Chuyen de Hoa Huu Co

MT S CHUYN HA HC HA HC HU C
duongtheh2ovn@gmail.com DNG TH
1
BI 1 I CNG PHNG PHP GII TON TRONG HU C
A.L THUYT
Hu ht dng bi ton lin quan n hp cht hu c thng l dng bi ton
t chy, v xc nh cng thc cu to, cng thc ha hc trong mt hp cht A.
Chng ta cng im qua mt s l thuyt, v cc dng ton ca hp cht hu c.
1. CC PHNG PHP BIN LUN XC NH CNG CNG THC HP
HP CHT HU C
1.1. Bin lun khi ch bit cng thc nguyn ca hp cht
Bi ton: Cho mt cng thc hu c A c dng tng qut CxHyOzNtXv (X =halogen).
Xc nh cng thc cng thc cu to ca A.
Gii
bt bo ha (s lng lin kt , s vng trong cng thc cu to ca A)
a =
2x+2-(y+v)+t
2
(1)
Da vo tnh cht ha hc chuyn v cc dng cng thc tng qut ca cc nhm
chc c cha trong A. (chng hn nh: Ru, ete, Xeton, aldehid, acid....)
Chuyn A c dng cng thc phn t v dng nu trong A c cha X: CnH2n+2-2a-zXz

A: CnH2n +2-2a-zXz _
n l s nguy t C trong A
a s lin kt trong A
z s nhm chc ca X

Ta lun c:
yH ca gc 2xC gc + 2 z (2)
Du = xy ra khi A l mt cht no
V d 1: Bin lun xc nh cng thc A ca mt acid hu c no mch h c
cng thc nguyn l (C2H3O2)n

2
Gii
Cch 1: xc nh CTPT ca A ta da vo bt bo ha
V trong A l mt acid hu c no mch h A c n lin kt
n=
2.2n+2-3n
2
= n =2 CTPT A: C4H6O4
Cch 2: p dng cng thc (2) v A l cht no nn: A c dng tng qut
CnH2n(COO)n C2nH3nO2n
2n =2n +2 n n =2 CTPT ca A: C4H6O4
V d 2 CTPT ca ru no A l CnHmOx. Hi m v n c gi tr nh th no A
l ru no:
Gii
V A ru no nn da vo cng thc tng qut xy dng mc l thuyt ta nh
dng c: CTTQ ca A l CnHm x (OH)x trong : m x =2n +2 x m =2n+2
Vy A l ru no th m =2n+2
Kt lun: CxHyOz l mt ru no th phi tha mn y = 2x+2
1.2. Bin lun khi ch bit MA
Bi ton Cho mt cng thc phn t c dng tng qut: CxHyOzNtClv, bit c khi
lng phn t ca hp cht A l MA. Xc nh cng thc A.
Gii
Nu A l hp cht hydrocarbon: CxHy th ta lun c:
_
M
A
=12x +y
y
hn
2x +2

T ta la chn gi tr nguyn ph hp. Nu cn thit da vo d kin bi ta c
th bit gii hn ca C (nu l kh x4).
Nu A l hp cht CxHyOz th ta bin lun theo oxy. V da vo d kin ca y
vi x thng qua xc nh c A.
V d 1 Xc nh cng thc ca hydrocarbon mch h ca A, c khi t khi so
vi H2 l 28. Xc nh A. Bit rng iu kin thng A th kh
Gii
Gi cng thc phn t tng qut ca A l: CxHy
MA =28.2 =56 g/ mol =12x+y(1)

3
]
y 2x+2
x 4
(2)
T (1) v (2) ta nhn thy: 56 14x+2 x 3,86 (3)
T (3) v (2) ta suy ra x =4 y =8 A l C4H8
V d 2 Mt hp cht ca A c cng thc phn t cha cc nguyn t C, H, O
c khi lng phn t l 60g/ mol. Xc nh A.
Gii
Gi cng thc hp cht ca A c dng CxHyOz. MA =12x+y+16z =60
z =
60-(12x+)
16
(1) bin lun theo z ta c: (1 z 2)
z=1 (1) tr thnh: 12x+y =44 (1x3) x =3, y =8 l nghim ph hp
z =2 (1) tr thnh: 12x+y =28 x =2, y =4 l nghim ph hp
Vy A c th l: C3H8O hoc A c th l: C2H4O2
1.3. Xc nh cng thc phn t trong cng mt dy ng ng
ng ng: l hin tng cc cht c cu to v tnh cht tng t nhau,
nhng v thnh phn phn t khc nhau mt hay nhiu nhm CH2. Nhng
cht c gi l nhng cht ng ng vi nhau, chng hp thnh mt dy
ng ng.
Theo nh ngha: Hp cht hu c l ng ng ca nhau, th chng s hp thnh
mt cp s cng c cng sai d =14 ( trong a1 l s hng u tin)
S hng cui an = a1 + (n-1)d (3)
Tng cc s hng:
Sn = (
a
1
+a
n
2
).n (4)
V d: Mt hp cht A c cha mt s cht hydrocarbon l dy ng ng ca
nhau. Khi lng phn t hydrocarbon ln nht gp 2,4 ln khi lng phn
t hydrocarbon nh nht. Tng khi lng phn t ca hydrocarbon trong A
l 204g/mol. Xc nh CTPT c trong A.
Gii
Gi Mmax l khi lng phn t ca hydrocarbon ln nht c trong A, Mmin l
khi lng phn t nh nht c trong A. Cc hydrocarbon trong A lp thnh
cp s cng c cng sai l 14

4
V trong A c cha cc hydrocarbon l ng ng ca nhau. p dng cc cng
thc 3, 4 ta lun c:
Mmax =Mmin +(n -1).14 (1) =2,4Mmin (1)
Sn =
M
max
+ M
mn
2
n =204 (2)
T (2) ta c:
3,4M
mn
2
*n =204 (3) lp t s (3) cho (2) ta c: n
2
n 12 =0
Gii ra ta c n =4, v n =-3 (loi) ta c n= 4 ta c Mmin =30g/ mol
Vy trong A bao gm c cng thc phn t hydrocarbon sau: C2H4, C3H6, C4H8, C5H10.
2. CC PHNG PHP XC NH CPTPT HP CHT HU C
2.1. Phng php 1
Nu mt hp cht A c cng thc phn t tng qut CxHyOzNt xc nh cng thc
phn t ca A ta c cng thc:
12x
m
C
=
y
m
H
=
1z
m
D
=
14t
m
N
=
M
A
a

a = mC + mH + mO + mN (5)
12x
%C
=
y
%H
=
1z
%D
=
14t
%N
=
M
A
1

2.2. Phng php 2: Xc nh cng thc phn t qua phn ng chy.
y l mt phng php ph bin nht, da vo phn ng chy xc nh cng
thc phn t.
CxHyOzNt +(x+
y
4
-
z
2
) O2 xCO2 +
y
2
H2O +
t
2
N2
a(mol) 44xa (g) 9ya (g) 14ta (g)
bi s cho bit cc d kin t d kin ta xc nh c cng thc phn t ca A.
Sau y xin gii thiu mt s cng thc tnh nhanh rt ra t phn ng chy, xc
nh cng thc A
Nu t chy 1 cht: S C : S H: S N = n
CD
2
: 2n
H
2
D
: 2n
N
2
(6)
S nguyn t Carbon trong A x =
n
CD
2
n
A
=
m
CD
2
44n
A
=
V
CD
2
22,4.n
A
(7)

5
S nguyn t Hydro trong A
y =
2.n
H
2
D
n
A
=
m
H
2
D
9.n
A
(8)
Bo ton nguyn t trong A mA = mC + mH + mO + mN (9)
Nhng h qu rt ra t phn ng t chy:
n
CD
2
= nA.S C (10)
n
H
2
D
=
S H
2
*nA (11)
T hai cng thc trn ta rt ra mt h qu quan trng:

S C
S H
=
n
CD
2
2n
H
2
D
(12)
i vi t chy mt hn hp ta s c:

S C
TB
S H
TB
=
n
CD
2
2n
H
2
D
(13)
V d 1 [Khi A - 2007] Khi t 1 amin n chc X, thu c 8,4 lt kh CO2,
1,4 lt kh N2 (cc kh o ktc) v 10,125gam nc. Xc nh CTPT ca X.
Gii
V A l amin n chc gi CTPT: CxHyNt
p dng cng thc (6): x:y:t =
8,4
22,4
: 2
1,4
22,4
: 2
10.125
18
=3:9:1 CTPT X: C3H9N
V d 2 Hn hp A gm 2 hydrocarbon c s mol bng nhau. t chy hn
hp A thy t l s mol ca CO2 vi H2O l 2:3. Xc nh cc hydrocarbon trong
A.
A.CH4, C2H6 B. C2H6, C3H8 C. C3H8, C4H10 D. CH4, C3H8.
Gii
p dng cng thc (12) ta c:
S C
TB
S H
TB
=
S C
TB
2
S H
TB
2
=
n
CD
2
2n
H
2
D
=
2
2.3
=
1
3


6
V hn hp A gm hai hydrocarbon c ch s mol l bng nhau, nn s CTB lun bng
trung bnh cng cc s C trong hydrocarbon trong A. p n D
V d 3 [D b H 2009] t chy 1.6 gam mt este E n chc c 3.52
gam CO2 v 1.152 gam H2O. Nu cho 10 gam E tc dng vi 150ml dung dch
NaOH 1M , c cn dung dch sau phn ng thu c 16 gam cht rn khan .
Vy cng thc ca axit to nn este trn c th l :
A. CH2=CH-COOH B. CH2=C(CH3)-COOH
C. HOOC(CH2)3CH2OH D. HOOC-CH2-CH(OH)-CH3
Gii
Ta tnh n
CO
2
=
3,52
44
=0,08 mol; n
H
2
O
=
1,152
18
=0,064 mol. p dng cng thc (12) ta c:
Trong hp cht este c t l:
S C
S H
=
n
CD
2
2n
H
2
D
=
,8
2,4
=
5
8
Cng thc phn t ca este c dng C5H8O2
Trong 10 gam este tng ng vi nE =
10
100
= 0,1 mol. Nh vy sau phn ng NaOH
cn d nNaOH d =0,15 0,1 =0,05mol mNaOHd =0,05.40 =2 gam. mmui =14gam
Mmui =
m
mu
n
E
=
14
0,1
=140 g/ mol Macid =140 (23 1) =118 g/ mol p n C
Cng thc cu to ca ca acid c dng: HOOC(CH2)3CH2OH. Dng este ca E l mt
este dng vng.

X l s liu ca phn ng CO2 tc dng vi dung dch kim.
CO2 l kh sinh ra t phn ng t chy phn ng
CO2 + dd kim d Mui trung ha
CO2 + dd kim _
HCD
3
-
CD
3
2-
Dng phng php bo ton nguyn t C
n
C
(CO2) = n
C(HCD
3
-
)
+ n
C(CD
3
2-
)

Khi lng ca bnh ng dung dch kim tng ln:
Mi hp cht hu c khi t chy: CnH2n+2-2aOx

7
nhchc =
n
H
2
D
-n
CD
2
1-h

mb = m
CD
2
+ m
H
2
D

Khi lng ca dung dch sau phn ng trong bnh tng ln:
mdd = m
CD
2
+ m
H
2
D
- m
Khi lng dung dch sau phn ng trong bnh gim xung:
mdd= m (m
CD
2
+ m
H
2
D
)
B. PHNG PHP GII
1. Phng php vit cc dng ng phn ca hp cht hu c
Hin tng cc cht c cng cng thc phn t nhng do cu to khc nhau nn
c tnh cht khc nhau, c gi l cc cht ng phn ca nhau.
V d: Vi cng thc C3H8O s c hai ng phn khc nhau, l ru v eter.
ng phn ca ru. (2 ng phn)
CH3 CH2 CH OH (n-propanol) CH3 CH CH3 (propan 2 ol)
OH
ng phn ete (1 ng phn): CH3 O CH2 CH3
vit c ng phn CxHyOzNtXz (X halogen) ca hp cht hu c ta cn
thc hin cc bc sau:
Bc 1 Xc nh bt bo ha qua cng thc
a =
2x+2-(y+v)+t
2

Bc 2 Xc nh cc nhm chc c trong phn t tng qut v da vo
bt bo ha trong mch. Xc nh cng thc cu to trong mch: mch h,
mch vng.
Bc 3 Vit cc dng ng phn m ta nh hng theo bc 2.
V d Vit cng thc cu to c th c ca C3H6O
Gii
bt bo ha: a =
2.3+2-6
2
=1 trong cu to ca hp cht ny c 1 lin kt
hoc 1 vng trong mch.

8
Trong mch mang nhm chc OH
CH2 =CH CH2 OH
Mch mang nhm chc ceton:
Mch mang nhm chc aldehid: CH3 CH2 CHO
Mch mang nhm chc ete
Ete khng no: CH2 =CH O CH3 (thng khng tn ti)
Ete vng no:

Gii thiu mt s cng thc tnh nhanh s ng phn:
1. Cng thc tnh s ng phn ancol n chc no, mch h : Cn H2n+2O2
S ng phn Cn H2n+2O2 = 2
n- 2
( 1 < n < 6 )
V d : S ng phn ca ancol c cng thc phn t l :
a. C3H8O =2
3-2
=2
b. C4H10O =2
4-2
=4
c. C5H12O =2
5-2
= 8
2. Cng thc tnh s ng phn anehit n chc no, mch h : Cn H2nO
S ng phn Cn H2nO = 2
n- 3
( 2 < n < 7 )
V d : S ng phn ca anehit n chc no, mch h c cng thc phn t l :
a. C4H8O =2
4-3
=2
b. C5H10O =2
5-3
= 4
c. C6H12O =2
6-3
= 8
3. Cng thc tnh s ng phn axit cacboxylic n chc no, mch h :
Cn H2nO2
S ng phn Cn H2nO2 = 2
n- 3
(2 < n < 7)
V d : S ng phn ca axit cacboxylic n chc no, mch h c cng thc phn
t l

9
a. C4H8O2 =2
4-3
=2
b. C5H10O2 =2
5-3
= 4
c. C6H12O2 =2
6-3
= 8
4. Cng thc tnh s ng phn este n chc no, mch h : Cn H2nO2
S ng phn Cn H2nO2 = 2
n- 2
(1 < n < 5)
V d : S ng phn ca este n chc no, mch h c cng thc phn t l :
a. C2H4O2 =2
2-2
=1
b. C3H6O2 =2
3-2
= 2
c. C4H8O2 =2
4-2
= 4
5. Cng thc tnh s ng phn ete n chc no, mch h : Cn H2n+2O
S ng phn Cn H2n+2O =
2
) 2 ).( 1 ( n n
( 2 < n < 5 )
V d : S ng phn ca ete n chc no, mch h c cng thc phn t l :
a. C3H8O =
2
) 2 3 ).( 1 3 (
=1
b. C4H10O =
2
) 2 4 ).( 1 4 (
= 3
c. C5H12O =
2
) 2 5 ).( 1 5 (
= 6
6. Cng thc tnh s ng phn xeton n chc no, mch h : Cn H2nO
S ng phn Cn H2nO =
2
) 3 ).( 2 ( n n
( 3 < n < 7 )
V d : S ng phn ca xeton n chc no, mch h c cng thc phn t l :
a. C4H8O =
2
) 3 4 ).( 2 4 (
=1

10
b. C5H10O =
2
) 3 5 ).( 2 5 (
= 3
c. C6H12O =
2
) 3 6 ).( 2 6 (
= 6
7. Cng thc tnh s ng phn amin n chc no, mch h : Cn H2n+3N
S ng phn Cn H2n+3N = 2
n-1
( n < 5 )
V d : S ng phn ca anin n chc no, mch h c cng thc phn t l :
a. C2H7N = 2
2-1
=1
b. C3H9N =2
3-1
= 3
c. C4H12N =2
4-1
= 6
8. Cng thc tnh s trieste ( triglixerit ) to bi glixerol v hn hp n axt
bo :
S tri este =
2
) 1 (
2
n n

V d : un nng hn hp gm glixerol vi 2 axit bo l axit panmitic v axit stearic
( xc tc H2SO4 c) th thu c bao nhiu trieste ?
S trieste =
2
) 1 2 ( 2
2
=6
9. Cng thc tnh s ng phn ete to bi hn hp n ancol n chc:
S ete =
2
) 1 ( n n

V d : un nng hn hp gm 2 ancol n chc no vi H2SO4 c 140
0
C c hn
hp bao nhiu ete? S ete =
2
) 1 2 ( 2
=3
2.Phng php bo ton nguyn t
Nguyn tc phng php Trong cc phn ng ha hc thng thng cc
nguyn t c bo ton.

11
H qu: T nh ngha ta nhn thy rng tng s mol nguyn t ca mt
nguyn t Z bt k no trc v sau phn ng u bng nhau.
Mt s lu
p dng tt phng php ny ta hn ch vit phng trnh phn
ng, ta nn vit dng s tm tt, trong chng ta s biu din cc
tm tt bi cho.
Nn quy v h s mol nguyn t ca tng nguyn t trong hp cht
hoc hn hp
Ch v h s, v hiu sut phn ng.
V d: t chy hon ton m gam hn hp Y gn CH4, C3H6, v C4H10 thu c 4,4
gam CO2 v 2,52 gam nc. m c gi tr l bao nhiu?
Gii
S bin i: _
CH
4
C
3
H
6
C
4
H
10
+O2 CO2 +H2O
T s phn ng ta c: mY =mC(CO2) +mH(H2O) =12*
4,4
44
+2*
2,52
18
=1,48gam
3.Phng php bo ton khi lng
Trong mt phn ng ha hc tng khi lng cht tham gia bng tng khi
lng sn phm to thnh.
m
T
=m
s

H qu: Cho phn ng dng tng qut A +B C +D
mA+mB =mC +mD t mi lin h ny ta i tm vi yu cu bi cho.
V d un132,8 gam hn hp 3 ru no, n chc vi H2SO4 c 140
o
C thu c
hn hp cc ete c s mol bng nhau v c khi lng l 111,2 gam. S mol ca mi
ete trong hn hp l bao nhiu?
Gii
Gi cng thc chung cho 3 ru no n chc l: R
OH
Phn ng tch nc: R
OH +R
OH
t
0
C
--: R
O - R
+H2O

12
S ete to thnh =
n(n+1)
2
=6 ete (n=3)
Theo nh lut bo ton khi lng ta c:
m
H
2
O
=mru - mete =132,8 111,2 =21,6 gam
Theo phn ng trn nete =n
H
2
O
=
21,6
18
=1,2mol nmi ete =
1,2
6
=0,2 mol
C. BI TON
Bi 1 [Khi A 2011] t chy hon ton 3,42 gam hn hp gm axit acrylic, vinyl
axetat, metyl acrylat v axit oleic, ri hp th ton b sn phm chy vo dung dch
Ca(OH)2 (d). Sau phn ng thu c 18 gam kt ta v dung dch X. Khi lng X
so vi khi lng dung dch Ca(OH)2 ban u thay i nh th no?
A. Tng 2,70 gam. B. Gim 7,74 gam. C. Tng 7,92 gam. D. Gim 7,38 gam.
Gii
PP: Bi ton ny i hi hc sinh cn phi nh cc cng thc ca cc cht m
cho.
CH2=CH COOH : acid acrylic; CH3COOCH2CH=CH2: Vinylaxetat
CH3 - ( CH2)7 - CH =CH -(CH2)7 COOH: acid oleic.
CH2=CH COOCH3: metylacrylat
Nhn xt: Cc acid v este u l dng n chc v c hai lin kt . Do vy cng
thc tng qut trung bnh ca hn hp trn c dng C
n
H
2n-2
O2.
Phn ng t chy: C
n
H
2n-2
O2 +
3n-3
2
O2 n CO2 +(n 1)H2O
a na (n 1)a
Theo bi ra ta c: n
CO
2
=0,18 mol =na mhh =(14n +30)a =3,42 a = 0,03 mol
n
H
2
O
= 0,15mol. Khi t chy ton b lng sn phm chy c dn vo bnh
ng Ca(OH)2 lm cho bnh nc vi tng ln.
msp chy =m
CO
2
+m
H
2
O
=0,18*44 +0,15*18 =10,62 gam
m =m
CO
2
+m
H
2
O
- m= 10,62 18 =-7,38gam p n D

13
Bi 2 [Khi A 2011] t chy hon ton x mol axit cacboxylic E, thu c y mol
CO2 v z mol H2O (vi z =y x). Cho x mol E tc dng vi NaHCO3 (d) thu c y
mol CO2. Tn ca E l
A. axit acrylic. B. axit oxalic. C. axit aipic. D. axit fomic
Gii
Khi t chy x mol E thu c y mol CO2 s CE =
x
(1)
Khi cho x mol E tc dng vi NaHCO3 thu c y mol CO2 S Cnhm chc =
x
(2)
T (1) v (2) ta nhn thy s CE =s Cnhm chc =
x
acid oxalic tha mn bi ton
Bi 3 [Khi A 2011] t chy hon ton x gam hn hp gm hai axit cacboxylic hai
chc, mch h v u c mt lin kt i C=C trong phn t, thu c V lt kh CO2
(ktc) v y mol H2O. Biu thc lin h gia cc gi tr x, y v V l
A. V =
28
( 30 )
55
x y . B. V =
28
( 62 )
95
x y C. V =
28
( 30 )
55
x y . D. V =
28
( 62 )
95
x y .
Gii
Lun nh dng cng thc tng qut ca hp cht hu c c cha C,H,O l
A: CnH2n +2-2aOz _
n l s nguy t C trong A
a s lin kt trong A
z s nhm chc ca O

y bi ton cho a = 3(v c 1 ni i C=C, v 2 lin kt trong nhm chc COOH)
Dng tng qut ca hn hp l CnH2n -4O4 nCO2 +(n-2)H2O
Gi a l s mol ca acid a =
n
H
2
D
-n
CD
2
1-h
y k = 3 a =
V
22,4
-y
2
(1)
Khi lng ca cc acid trong hn hp: (14n +60)a =x (2)
T (1) v (2) ta c: 14na +60a =x 14*
v
22,4
+60*
V
22,4
-y
2
=x x =
55
28
V -30y
V =
28
55
(x +30y) p n C

14
Bi 4 [Khi A 2011] Hn hp X gm C2H2 v H2 c cng s mol. Ly mt lng hh X
cho qua cht xc tc nung nng, thu c hh Y gm C2H4, C2H6, C2H2 v H2. Sc Y vo
dd brom (d) th khi lng bnh brom tng 10,8 gam v thot ra 4,48 lt hh kh
(ktc) c t khi so vi H2 l 8. Th tch O2 (ktc) cn t chy hon ton hn hp
Y l
A. 22,4 lt. B. 44,8 lt. C. 26,88 lt. D. 33,6 lt.

Gii
Tm tt:
+Br2

V1 V2 V3
Phng php: Bo ton khi lng mX =mY =mz +mT
Khi lng bnh brom tng ln: chnh l mz

Gi ta i tnh khi lng mT lc ta s tm c mX v mY. C th ta c li gi nh
sau:
M
Z
=8.2 =16g/ mol mz =16*
4,48
22,4
=3,2gam
mY =mX =10,8 +3,2 =14 gam 26a + 2a = 14 a = 0,5mol
t chy hn hp Y cng nh t chy hn hp X.
C2H2 +
5
2
O2 2CO2 +H2O (1)
H2 +
1
2
O2 H2O
Tng s mol oxy tham gia phn ng t chy l:
5
2
a +
1
2
a =3a =1,5 mol
V =22,4*1,5 =33,6 lt p n D
C
2
H
2
+H
2

hhY: C
2
H
4
, C
2
H
6
,
C
2
H
2
, H
2

m=10,8g
Kh T:
4,48 lt
m
Z
=m
dd brom


15
Bi 5 [Khi A 2011] t chy hon ton 0,11 gam mt este X ( to nn t mt axit
cacboxylic n chc v mt ancol n chc) thu c 0,22 gam CO2 v 0,09 gam
H2O. S este ng phn ca X l:
A. 2 B. 5 C. 6 D.4
Gii
n
CO
2
=
0,22
44
=0,005mol; n
H
2
O
=
0,09
18
=0,005 mol n
CO
2
=n
H
2
O

este em t l no n chc: CnH2nO2. Bo ton nguyn t ta s c
mO trong este =0,11 0,005*12 0,005*2 =0,04gam neste =
0,04
32
=0,00125 mol
S CX =
0,005
0,00125
=4 S HX =4 CTPT ca X l C4H8O2. Este no n chc n=4
p dng cng thc tnh s ng phn nhanh ta s c: s ng phn =2
n-2
=4
p n D


16
BI 2 ALKAN (PARAFIN) CnH2n+2 ( n 1)
A.KIN THC C BN
I. TNH CHT VT L
Dng tn ti ca alkan
Alkan tng ti th kh vi n =1 4
Alkan tn ti th lng vi n =5 16
Alkan tn ti th rn vi n 17
Alkan khng tan trong nc, trong mch ca chng ch c tng tc van der
Waals, nhit si tng nu phn t lng ca chng tng. Alkan tan rt tt
trong dung mi khng phn cc.
II.TNH CHT HA HC
1. Phn ng t chy (oxy ha hon ton)
Alkan t chy sinh ra lng nhit rt ln, sn phm thu c l nc v kh
CO2
CnH2n+2 +
3n+1
2
O2 nCO2 +(n+1)H2O +Q
Nhn xt: Khi t chy alkan ta c:
n
CO
2
<n
H
2
O

2. Phn ng dehydro ha
Phn ng dehydro ha alkan l mt phn ng phc tp, ty theo nhit , p
sut, cht xc tc m c nhng sn phm khc nhau.
CnH2n +H2 (alken)

CnH2n +H2 (cyclo alkan)
CnH2n+2 t
0
, P, xt CnH2n-2 +2H2 (alkin)
CnH2n -6 +4H2 (aren)
c bit: 2CH4 1500
0
C CH CH + 3H2
lm lnh nhanh
3. Phn ng th halogen
n
alkan
= n
H
2
O-
n
CO
2


17
n=m +v
n 3
Phn ng th ca alkan vi halogen l mt phn ng khng chn lc, c ch
xy ra theo c ch gc.
CnH2n+2 + Cl2 as CnH2n+2-X + HX
Kh nng th ca halogen:

c im ca phn ng th: Phn ng u tin cho carbon bc cao.

V d: (51%)

CH3CH2CH3 +Cl2
CH3CH2CH2Cl (49%)
4. Phn ng crackinh
Phn ng crackinh l phn ng b gy phn t c s C ln thnh nhng alken
v alkan c s C nh hn.
CnH2n+2 CmH2m + CvH2v+2
Ta lun c:

III. IU CH
1. Cng hydro t alken,alkin vi cht xc tc thch hp
Phn ng cng hydro vi cht xc tc Ni, nhit cao sinh ra alkan
CnH2n +H2 Ni CnH2n+2
CnH2n-2 +2H2 Ni CnH2n+2
2. Phng php tng mch carbon
Phn ng lm tng mch carbon dng mch i xng da vo phn ng
Wurtz
RX +Na R R +NaX
Phn ng ny khng dng iu ch nhng alkan bt i xng.
3. T hp cht dialkyl ng litium
Ngi ta s khc phc phn ng Wurtz bng phn ng ny iu ch nhng
alkan bt i xng. Phn ng ny c hai nh ha hc E.J.Corey v Herbert
Flo>Clo>Brom>Iod
m
T
=m
s

n
T
<n
S

18
House pht hin c lp vi nhau. Phn ng ny c thc hin gia dialkyl
ng litium, R2CuLi, v halogen RX (R c th ging hoc khc R).
R2CuLi + RX R R +RCu +LiX
Hiu sut phn ng t tt nht khi R l mt alkyl nht cp, cn R c th l
nht, nh hay tam cp u c.
4. Hon nguyn halogenur alkyl
Halogenur RX c th b kh halogen trong mi trng acid proton v xc
tc l km.
R X
H
+
,Zn
-- R H
5. T tc cht Grignard
Cho tc cht Grignard RMgX tc dng vi nc ngi ta thu c mt alkan
tng ng.
RMgX
H
2
O
-- R H
6. Phng php gim mch carbon
Ngi ta i t mui acid v cc kim loi kim: RCOONa trn vi xt v cht
CaO mc ch lm kh hn hp phn ng v ngn khng cho khng cho NaOH
n mn thy tnh.
RCOONa + NaOH
vI tI,xt
-- Na2CO3 +RH
Mt s phng php iu ch kh Metan
Al4C3 + H2O Al(OH)3 +CH4
C + H2
NI,500
0
C
-- CH4
CH3COONa + NaOH
vI tI,xt
-- CH4 +Na2CO3
Trng hp c bit ca phn ng:
2HCOOK + 2NaOH
vi ti,xt
-- H2 + Na2CO3 +K2CO3
7. Phn ng crakinh
IV.VN CN BIT
S ha gii alkan trong k ngh du ha cn c gi bng thut ng chuyn
mn l crackinh. C nhiu dng crackinh ty theo quy trnh sn xut ca cc
cng ty ha du trn th gii. Trong nhit crackinh, alkan c cho i ngang
qua mt phng un nng nhit rt cao. Nhng alkan kch thc ln c
chuyn sang nhng alkan c s Carbon nh hn, alken v hydro. Trong hi

19
nc cracking hydrocarbon c ha tan vo trong hi nc un nng
nhanh nhit 700 900
0
C / giy ri lm ngui cng tht nhanh. Trong
hydrocrackinh, phn ng c thc hin di s hin din ca ca hydrogen
v xc tc p sut cao, nhng nhit thp hn (250 400
0
C). Trong tt c
cc loi crackinh th xc tc crackinh l quan trng nht trong k ngh ch
bin du m v khng ch lm tng thm khi lng xng t s ct t nhng
hydrocarbon dy di thnh dy ngng hn m cn lm gia tng cht lng
ca xng. S crackinh ny c thc hin bng cch dn hi hydrocarbon
(un du m nhit cao) ngang qua xc tc silic alumin mn nhit
450
0
C v di p sut nh.
Di nh hng ca nh sng t ngoi (h) hoc nhit 200 400
0
C, clor
v brom tc dng vi alkan cho ra cloroalkan v bromo alkan v mt lng
HCl v HBr tng ng. S clor ha cho hn hp sn phm khng c ng
phn no tri hn, trong khi brom s cho mt sn phm chnh. Do s
clor ha ch dng trong k ngh iu ch dung mi khng tinh khit. Tri
li s brom ha s dng trong phng th nghim iu ch cc bromur alkyl
tinh khit vi hiu sut cao. Phn ng clor ha xy ra theo c ch gc t do
gm ba giai on chnh: giai on khi mo, giai on truyn, giai on kt
thc.
Vi alkan v c nhng c im v c cu nn c nhng phn ng biu tnh
sau:
Khng tan trong nc, dung dch baz, acid long. l c tnh ca tt
c cc hydrocarbon
Khng tan trong acid sulfuric m c, lnh. Nhng hp cht c cha
mt s nhm nh chc c oxygen hay nitrogen hoc bt bo ha u tan
c trong acid sulfuric m c lnh. Ngoi tr alkan, halogenur alkyl,
aren.
B.PHNG PHP GII TON
VN 1 DNG TON T CHY ALKAN
CnH2n+2 +
3n+1
2
O2 nCO2 +(n+1)H2O +Q
Khi t chy alkan ta lun lun c:
n
CD
2
< n
H
2
D
nalkan = n
H
2
O-
n
CO
2


20
n 3
S C trong alkan =
n
CD
2
n
H
2
D-
n
CD
2
S H trong alkan =
2 n
H
2
D
n
H
2
D-
n
CD
2

Nu t chy hydrocarbon m c n
CD
2
< n
H
2
D
kt lun ngay
hydrocarbon em t chy l Alkan.
VN 2 DNG CRACKINH ALKAN.
(X) (Y)

mX = mY
n=m +v
M
X
=
m
X
n
X
=
m
Y
n
X
=M
Y
*
n
Y
n
X
=
V
Y
V
X
*M
Y

y l dng cng thc tnh ton cho mi bi ton crackinh, nn vic tnh ton cho
phn ng rt n gin v hiu qu.
Dng bi ton quen thuc trong phn ng crackinh

Alkan
crackinh
+Br2
V (l)

V1 V2 V3
Da vo phn ng ta c: _
n
AIkan
= n
aIkcn
=n
AIkan
s
n
AIkan
b
= n
p
+n
d
H=
p
b
100%
_
V =V
3
V
p
= V
1
V
3
H=
V
1
-V
3
V
3
100%

y l cng thc quan trng mc d n i t nhng nhn xt ht sc thun ty,
nhng vic gii ton rt hiu qu, c ng dng rt nhiu trong thi i hc.

Alkan
sp

Alken
Alkan
d

Alken
+dd
Br
2

Alkan
sp

Alkan
d
n
alkan p
=n
alken
=n
Alkan sp

21
C. BI TP
Bi 1 t chy hon ton mt lng hirocacbon A thu c 26,4 gam CO2 v 16,2
gam H2O . Tm cng thc phn t ca A ?
Gii
n
CO
2
=
26,4
44
=0,6 mol; n
H
2
O
=
16,2
18
=0,9 mol. A thuc dy ng ng Alkan
S CA =
n
CO
2
n
H
2
O-
n
CO
2
=
0,6
0,9-0,6
=2 CTPT ca A: C2H6
Bi 2 [Khi A 2008] Khi crackinh ton b mt th tch alkan X thu c ba th tch
hn hp Y (cc th tch o cng iu kin nhit v p sut). T khi hi ca Y so
vi H2 l bng 12. Cng thc phn t ca X?
A. C6H14 B. C3H8 C. C4H10 D. C5H12
Gii
p dng cng thc M
X
=
m
X
n
X
=
m
Y
n
X
=M
Y
*
n
Y
n
X
=
V
Y
V
X
*M
Y
=
3
1
*12*2 =72g/ mol
CTPT ca X l C5H12 p n D
Bi 3 Khi crackinh ton b V lt alkan X thu c 35 lt hn hp Y gm 7 cht. Dn Y
qua bnh ng dung dch nc brom Br2 d, thy cn 20 lt. Gi tr V v hiu sut
phn ng l bao nhiu?
Gii
p dng cng thc tnh ton phn phng php gii ton (c k phn phng
php gii) ta s tnh ra nhanh.
V =V3 =20 lt
Hiu sut phn ng: H=
V
1
-V
3
V
3
100% =
35-20
20
*100% =75%
Bi 4 Crackinh hon ton mt alkan A thu c mt hn hp kh B gm hai alkan v
hai alken. T khi hi ca B so vi H2 l 14,5. Khi dn dung dch qua bnh ng dung
dch brom d, khi lng hn hp kh gim i 55,52%. Tm cng thc phn t ca A,
xc nh % th tch cc kh trong B

22
Gii
Phng trnh phn ng crackinh:
D + E
A
Crackinh
Alkan Alken hhB
F + H
Alkan Alken
Theo phn ng ta nhn thy: nB =2nA M
A
=
m
A
n
A
=
m
E
n
A
=M
Y
*
n
E
n
A
=14,5*2*2=58g/ mol
14n +2 =58 n =4 CTPT A l: C4H10
Nu A l C4H10 th D, F ln lt l: CH4, C2H6, v E, H l C3H6, C2H4.
Gi a,b ln lt l s mol ca C3H6 v C2H4 : 42a +28b =0,5552.58(a+b) b =
7
3
a (1).
(1)
====%V
CH
4
=%V
C
3
H
6
=
u
2(u+b)
100% =
u
2(u+
3
u)
*100% =15% %V
C
2
H
6
=%V
C
2
H
4
=35%
Bi 5 t chy 19,2 gam hn hp gm 2 alkan k tip nhau, thu c V lt CO2
(0
o
C,2atm). Cho V lt CO2 trn i qua dung dch Ca(OH)2 th thu c 30g kt ta.
Nu tip tc cho Ca(OH)2 cho n d th thu c 100g kt ta na. Xc nh cng
thc phn t ca 2 alkan v % th tch cc alkan trong hn hp.
Gii
Gi cng thc phn t tng ng ca hai alkan trong hn hp l: C
n
H
2n+2

Phng trnh phn ng t chy: C
n
H
2n+2
+
3n+1
2
O2 nCO2 +(n +1)H2O
2CO2 + Ca(OH)2 Ca(HCO3)2 +H2O
CO2 + Ca(OH)2 CaCO3 + H2O
Ca(OH)2 + Ca(HCO3)2 2 CaCO3 + H2O
p dng nh lut bo ton nguyn t C (CO2) =
100+30
100
=1,3 mol =na (1)
(14na +2)a =19,2
(1)
===== a =0,5 mol n=2,6 n1 =2 <n <n2 =3

23
Vy cng thc phn t alkan trong hn hp l: C2H6 v C3H8.
Theo cng thc n =
2x+3(0,5-x)
0,5
=2,6 x =0,2 %V
C
2
H
6
=
0,2
0,5
100% =40%.
Bi 6 Mt hn hp X gm hai hydrocarbon lin tip nhau trong dy ng ng v
u th kh (ktc). t chy X vi 64g O2 ly d thu c hn hp kh, dn hn
hp kh i qua bnh ng dung dch Ca(OH)2 d th c 100g kt ta v cn li mt
kh thot ra c 11,2 lt (0,4atm, 0
0
C). Xc nh CTPT hydrocarbon trong X?
Gii
V O2 em t ly d, nn kh thot ra sau cng l kh O2 cn d sau phn ng t
chy.
S mol kh O2 tham gia vo phn ng t chy =
64
32
-
0,411,2
22,4
23
273
=1,8 mol
Gi cng thc phn t tng ng ca cc hydrocarbon c trong X: C
x
H
y

Phn ng t chy ca hn hp X l C
x
H
y
+(x +
y
4
)O2 xCO2 +
y
2
H2O
n
CO
2
=
100
100
=1 mol =xa
ya
2
=2(1,8 1) =1,6 mol n
CO
2
<n
H
2
O

hn hp X l dy ng ng ca alkan a =1,6 -1 =0,6mol x =
1
0,6
=
5
3

CTPT c trong X l CH4, C2H6.
Bi 7 em crackinh mt lng n butan thu c mt hn hp A gm 5
hydrocarbon kh. Cho hn hp kh ny i qua bnh ng dung dch nc Br2 d th
khi lng brom tham gia phn ng l 25,6g v sau th nghim khi lng bnh
brom tng ln 5,32g. Hn hp kh X cn li sau khi i qua dung dch brom c t khi
hi so vi mtan l 1,9625. Tnh hiu sut phn ng.
Gii
V butan crackinh sn phm thu c l 5 cht: CH4, C2H6, C4H10 d , C2H4, C3H6.
n
Br
2
=
25,6
160
=0,16 mol nbutan p =
1
2
nAlken=
1
2
n
Br
2
=0,08mol
M
hhX
=1,9625*16 =31,4g/ mol; dung dch brom tng ln chnh l khi lng ca
alken tham gia phn ng.

24
Vy ta s tnh c M =
5,32
0,16
=33,25g/ mol
M1 =28 8,75
M
=33,25
M2 =42 5,25
n
C
2
H
4
=0,16*
8,75
5,25+8,75
=0,1 mol =n
C
2
H
4
n
C
3
H
6
=0,06 mol =n
CH
4

n
C
4
H
10
b
=n
C
4
H
10
p
+n
C
4
H
10
d
=0,08 +a (1)
Hn hp kh X sau khi thot ra khi dung dch bnh nc brom: CH4, C2H6, C4H10.
H
hh
alkan sp =
160,06+300,1
0,16
=24,75 g/ mol; M
hhX
=1,9625*16 =31,4g/ mol

Ta vn dng quy tc ng cho

24,75 26,6
31,4
58 6,65

0,16
u
=
26
6,65
a = 0,04 mol (2)
T (1) v (2) ta suy ra nbutan =0,08 +0,04 =0,12 mol H =
0,08
0,12
*100 =66,67%
Bi 8 Sau khi kt thc phn ng crackinh n butan thu c 22,4 lt hn hp A (gi
s ch gm c cc hydrocarbon). Cho A li t t qua dung dch brom d ch cn
13,44 lt kh B. t chy hon ton 0,6 lt kh B thu c 1,3 lt kh CO2. Tnh hiu
sut phn ng. Bit rng cc kh o cng ktc

Gii
Phn tch: i vi dng bi ton ny ta nn biu din dng s tm tt thun
tin hn trong vic gii bi ton, cc bn nn c li phn hng dn gii dng bi
tp ny.

25

Tm tt:
Crackinh 0,6 lt B +O2
1,3 lt CO2
V
V1 V2
p dng cng thc tnh hiu sut phn phng php gii ta c:
H =
V
1
-V
2
V
2
*100% =
22,4-13,44
13,44
=66,67%
Bi 9 t chy hon ton mt hn hp X gm hai hydrocarbon k tip nhau trong
dy ng ng thu c V
CO
2
: V
H
2
O
= 12 : 23. Xc nh cng thc phn t ca hai
hydrocarbon v phn trm th tch ca mi hydrocarbon c trong hn hp.
Gii
V t chy hai hydrocarbon thuc dy ng ng c
V
CO
2
V
H
2
O
=
12
23
<1 X thuc dy
ng ng ca Alkan. p dng nh lut bo ton nguyn t ta c:
n
n+1
=
12
23
n =
12
11
n1 =1 <n <n2 =2 A: CH4 (a mol) ; B:C2H6 (1 a (mol))
p dng tnh cht trung bnh ta c:
a+2(1-a)
1
=
12
11
a =
10
11
%V
CH
4
=90,91%
Bi 10 Trong mt bnh kn th tch 1 dm
3
c mt hn hp ng th tch gm
hydrocarbon A v O2 nhit 133,5
o
C, 1atm. Sau khi bt tia la in ln v a v
nhit ban u th khi lng nc to ra l 0,216g. Tm CTPT ca A.
Gii
Theo phng trnh kh l tng: pV =nRT n =
pV
RT
=
1.1
0,082.(237+133,5)
0,03 (mol)
V hn hp l ng mol nn nA =n
O
2
=
0,03
2
=0,015 (mol)
n
O(
CO
2
)
=2.0,015 -
0,216
18
=0,018 mol n
CO
2
=
n
O(
CO
2
)
2
=0,009mol
C
4
H
10

hh A
V =22,4 l
hhB
V =13,44l

26
Trong A c
S C
S H
=
n
CO
2
2n
H
2
O
=
0,009
20,012
=
3
8
A : C3H8
BI 3 CYCLO ALKAN CnH2n (n 3)
A. KIN THC C BN
I. TNH CHT VT L
im si v t trng ca cyclo alkan n hon thng cao hn alkan chi
phng tng ng.
Cyclo alkan khng tan trong nc nhng tan trong dung mi hu c t
phn cc.
II. TNH CHT HA HC
1. Phn ng chy
Khi t chy cycloalkan trong iu kin y khng kh oxygen, mt
nhit lng ti a ta ra c th o c gi l thiu nhit.
CnH2n +
3n
2
O2 nCO2 + nH2O +Q
Nhn xt: Khi t chy cyclo alkan ta lun c: n
CO
2
=n
H
2
O

2. Phn ng th
Di s xc tc ca nh sng hoc nhit , cyclo alkan cho phn ng th
gc t do nh alkan.
+ Cl2
us kt
===== + HCl
Cyclopropan cloro cyclopropan
3. Phn ng m vng
Phn ng ch yu xy ra i vi vng cng nh cyclopropan v
cyclobutan, sn phm l nhng hp cht ch phng tng ng. (vng 3,
vng 4 lm mt mu ung dch brom trong dung mi CCl4)
+ Br2 Br CH2 - CH2 CH2 Br

III. IU CH
1. Phn ng Wurtz
Phn ng Wurtz thng c thc hin trn cht nn l dihalogenur, xc
tc l kim loi Zn, hoc Na.


27
Phn ng ch thc s tt khi iu ch cyclopropan

Zn/ CCI
4
====== +ZnBr2

2. Phn ng cng to vng
Khi cho carben tc dng vi dung dch alken s cho ra cyclopropan
tng ng.
V d:
CH3CH=CHCH3 + CH2N2
hy
====
PHNG PHP GII BI TP
Ch yu dng bi tp ca cycloalkan lin qua n phn ca alken.
Chng ta ch cn nh c im ca cycloalkane vng 3 v vng 4 c th
tham gia vo qu trnh m vng nn chng c th lm mt mu dung
dch brom.
Dng phn ng t chy, khi t chy cycloalkan lun c
n
CD
2
= n
H
2
D

iu ny cng xy ra khi t chy alken.


28
BI 4 ALKEN CnH2n (OLEFIN) (n 2)
A. KIN THC C BN
I. TNH CHT VT L
Dng tn ti ca alken iu kin thng:
Th kh tng ng vi: n =2 4
Th lng tng ng vi n =5 18
Th rn n 19
Nhit si v nhit nng chy tng i thp, kh nng tan trong
nc km.
V trong alken ni i nn chng s xut hin phn cc, trong khng
gian n s hnh thnh hai dng E (cis) v Z (trans). Dng Z c nhit
nng chy cao hn dng E, nhng li c nhit si thp hn E.
II. TNH CHT HA HC
1. Phn ng oxy ha
a. Phn ng oxy ha hon ton (phn ng t chy)
Alken t chy sinh sn phm thu c l kh CO2 v hi nc v nhit
lng sinh ra.
CnH2n +
3n
2
O2 nCO2 + nH2O +Q
a na na
Phn ng t chy ca alken cng ging nh t chy ca cycloalkan lun
c:

H qu

S C (alken) =
n
CO
2
n
A

S H (alken) =
2n
H
2
O
n
A

Khi t chy mt hydrocarbon c n
CO
2
=n
H
2
O
th hydrocarbon l
cycloalkan hoc alken.
b. Phn ng oxy ha khng hon ton
Ngi ta iu ch aldehid trong cng nghip bng cch oxy ha nh cc
alken c ni i u mch.
V d: 2CH2 =CH2 + O2
PdCI
2
/ CuCI
2
========= 2CH3CHO
n
CO
2
=n
H
2
O


29
Oxy ha ni i alken thnh cc diol di tc nhn ca cht oxy ha mnh
KMnO4.
3CnH2n +2KMnO4 +4H2O CnH2n(OH)2 +MnO2 + 2KOH
V d: CH2=CH2 +KMnO4 +H2O + 2MnO2 + 2KOH
(hng) (en)

H qu: Dng KMnO4 nhn bit alken v alkin.
Nu dng cht oxy ha mnh nh: K2Cr2O7 phn ng s ct t ni i
trong alken to ra cc acid hoc aceton.
V d: +[O]
K
2
Cr
2
O
====== +CH3COOH

H qu: Phn ng ny dng nhn bit c ni i u mch v gia
mch ca alken.
2. Phn ng cng
a. Phn ng cng halogen
Phn ng ca alken v halogen din ra mt cch d dng i vi clo v
brom sn phm sinh ra l 1,2 di-halogenalkan.
CnH2n +X2
CCI
4
====== CnH2nX2
Ring i vi brom phn ng cng lm mt mu dung dch brom nn dng
nhn bit c nhng hydrocarbon ni i.
Ngi ta ng dng phn ng cng vng ny sn xut ra clorur polyvinil
(PVC).
b. Phn ng cng hydrogen
Phn ng cng hydrogen to ra alkan vi cht xc tc thng l Nikel.
CnH2n + H2
NI/ t
0
==== CnH2n +2
c. Phn ng cng HX (tc nhn bt i xng)
Quy tc Markovnikov: trong s cng hydracid vo ni i C=C, hydrogen
ca hydracid s gn vo carbon mang nhiu hydrogen nht y l sn
phm chnh ca alken phn ng cng HX.
Gii thch quy tc: H
+
- X
-
l mt cht phn cc nn theo quy tc in ni
no mang in dng th in tch m s tc kch vo, cn ni no mang
in m th in tch dng tc kch vo. y C cng nhiu H th cng m

30
H
+
tc kch vo, tng t X
-
s tc kch vo C t H hn.

V d: + HBr

Th t phn ng cng vo alken ca HX: HI >HBr >HCl>HF
d. Phn ng cng H2O
Phn ng cng H2O ca alken cng tun theo quy tc Markovnikov. Sn
phm ca phn ng ny l cc alcol, di s xc tc H
+
.
V d:
CH2=CH CH2 CH3 +H2O
H
+

====

3. Phn ng trng hp (a phn ha)
Phn ng ny gn lin vi thc tin vi i sng ca con ngi, c th ni
polyme c rt nhiu trong i sng, v n tr thnh vt liu thng dng. Cc
polymer ny thng c thc hin bng cc phn ng polymer ha t
nhng monomer.
Mt s monomer v polyme tng ng:
Monomer Cng thc Tn thng mi
polymer
Etylen H2C=CH2 Polyethylen (PE)
Propylen H2C=CHCH3 Polypropylen(PP)
Cloroetylen H2C=CHCl Poly(vinyl
chloride) (PVC)
Styren H2C=CH-Ph Polystyrene (PS)
Tetrafluoroetylen F2C=CF2 Teflon
Metacrylat metyl H2C=C(CH3)CO2Me Lucite
Acetat vinyl H2C=CHOAc Polyvinyl acetat
(PVA)

4. Phn ng ozon
S ozon gii gm ba giai on: cng ozon (O3) vo ni i, chuyn v nhanh
chng to ra ozonid, thy gii ozonid ra hai hp cht carbonyl (aldehid, ceton
tng ng).


31
V d: CH3CH2CH=CHCH3 +O3
zn/ H
2
0
====== CH3CH2CHO +CH3CHO
CH3CH=CHCH3 +O3
zn/ H
2
0
====== 2CH3CHO
CH3CH2CH=CCH3 +O3 CH3CH2CHO +
CH3
III. IU CH ALKEN
1. Kh nc ca alcol
Di s xut hin ca acid H3PO4 hoc H2SO4 hoc ngi ta dng
cht xc tc acid Lewis, nhit cao. Sn phm thu c l mt
alken.
V d: CH3CH2OH
H
+
,170
0
C
======= CH2=CH2 +H2O
CH3CH2CH2CH2OH
H
+
,170
0
C
======= CH3CH=CHCH3 +H2O
Lu :
Phn ng tch nc tun theo quy tc Zaixep
phn ng tch nc ca alcol l bc III >II >I
Phn ng tch nc ca alcol bc III thng xy ra phn
ng chuyn v.
2. Kh hydracid ca halogenur alkyl
Phn ng c nung nng v cht xc tc baz mnh thng l KOH trong mi
trng C2H5OH (EtOH)
V d: CH3CHCH3 +KOH
Lt0H,A
===== CH2=CHCH3 +KBr +H2O
Br
phn ng ca RX: R-I >R-Br, R-Cl >R-F, cn gi l hiu ng nguyn t.
3. Kh halogen ca dihhalogenur
dihhalogenur: cn gi l vic dihalogenur (vicinalis: k cn)
Phn ng c xc tc bng kim loi thng Zn, Mg, I
-

V d: CH3CHCH2CH3
Zn (bt)/ EtOH
=========== CH3CH=CHCH3
Br
4. Hydrogen ha xc tc
Phn ng hydrogen ha xc tc alkin, xc tc thng s dng l xc tc
Lindlar (Pd mn, Pb bt, v quinolin). Phn ng s ngng giai on Alken.
R C C R
H
2
/ Pd
====
(Z) Alken (Z =cis)

32
Nu dng cht xc tc Na/ NH3 (lng) th phn ng s to (E) Alken
5. Phn ng cracking
Alken c iu ch t phn ng cracking t cc alkan c s C ln di s
xc tc: Zeolite (cht ch yu dng trong cng nghip ha du). Hoc cracking
di iu kin nhit v p sut cao (Xc tc khng chn lc).
CnH2n+2
Xt,P
=== CmH2m + CvH2v+2
IV. NGUN K NGH
Trong k ngh, ch yu l k ngh ha du, hu ht l cc etylen v propylen
c iu ch t s cracking nhng alkan c trong kh thin nhin (1C 4C)
v nhng alkan c trong chng ct phn on c nhit si thp (4C 8C).
V mt k thut c nhiu phng php cracking. S cracking nhit ch yu
cho l etylen. S cracking hi nc ch yu l etylen, propylen, butadien,
isopren v cyclopentadien.
Nhng alken dy di hn c iu ch t s cracking nhng phn on
chng ct c nhit si cao hn. Nhng alken ny hoc c lp lm cht
nn cho cc phn ng tng hp hu c hoc khng c lp nm li trong
xng lm tng gi tr ca xng .
Etylen v propylen l hai alken n gin nht, c iu ch nht trong k
ngh. Vo khong 26 triu tn etylen, v 14 triu tn propylen c iu ch
ra ti M hng nm, chng c dng lm nguyn liu iu ch propylen,
etylen glycol, acid acetic, acetaldehyd, v nhiu hp cht khc.
B. PHNG PHP GII TON
VN 1: PHN NG HYDRO HA ALKIIN
Phn ng khng nh lng:
CnH2n-2 + 2H2
N|,t
=== CnH2n+2
CnH2n-2 + H2
Pd,t
==== CnH2n
Trong phn ng khng nh lng
C2H2 + H2
Xt,t
=== _
C
2
H
6
C
2
H
4
C
2
H
2
H
2

i vi dng ton phn ng hydro ha alkin chng ta cn nh nhng iu c bn
sau:
Ty vo cht xc tc bi cho bit sn phm: alken, alkan

33
Dng nh lut bo ton khi lng:
mt =ms
Tm tt s dng ton ca phn ng hydro ha alkin nh sau:

dd Br2

Da vo s tm tt trn ta c cc cng thc ng nh sau, gii quyt c
vi mi bi ton cho cc dng phn ng hydrogen ha alkin.

VN 2: HIU SUT PHN NG HYDROGEN HA ALKEN
Dng phng php 3 bc:
CnH2n + H2
N,t
0
=== CnH2n+2
x (mol) y(mol)
a a a
x-a y-a a (mol)
X
Y
Z
T
m
X
=m
Y
=m
z
+m
T

m
Br
2
= m
z
=m
X
- m
T

34
Gi x, y l s mol ban u alken v hydrogen tham gia phn ng, a l s mol
phn ng ca phng trnh.
Hiu sut phn ng hydrogen phn ng:

Nu x y
Nu y x
Phn ng hydrogen ha alken lun c

t chy hn hp sau cng ging nh t chy hn hp kh ngc li.
VN 3 PHN NG CNG Br2
Hn hp alken tc dng vi dung dch Br2
CnH2n + Br2
CCI
4
=== CnH2nBr2
S mol alken tham gia phn ng vi Br2:

Khi lng bnh brom tng

gim s mol:

Mt s lu :
Dung dch mt mu: dd Br2 thiu, alken d
Dung dch phai mu: Br2 d, alken ht.
VN 4 HN HP ALKEN V ALKAN T CHY
Cho mt hn hp gm alkan v alken em t chy, thu c kh CO2,
H2O xc nh cc hydrocarbon c trong hn hp.
H =
u
x
.100%
H =
u
*100%
m
T
=m
s
n
H
2
p
=nt ns
n
Br
2
=nalken p
m =m
alken p
n =nt - ns =nalken p

35
Gi CnH2n+2 (x mol), CmH2m (y mol). Dng nh lut bo ton nguyn t C
nx +my =n
CO
2

Da vo bi ton ta xc nh c mi lin h, ngoi phng php
thng thng (phng php 3 bc). Ta cng c th p dng cng thc
tnh cht gi tr trung bnh.

C. BI TP
Bi 1 un nng hn hp kh gm 0,12 mol C2H2 v 0,18 mol H2 vi xc tc Ni, sau
mt thi gian thu c hn Y. Dn ton b hn hp Y li t t qua dung dch brom
d th cn li kh Z gm 0,06 mol C2H6 v 0,02 mol H2. Khi lng dung dch brom
tng ln l bao nhiu?
Gii
y l dng ton m trnh by trn (cc bn xem li phng php gii).
p dng nh lut bo ton khi lng: mX =mY =m + mZ
Khi lng dung dch brom tng ln: m = mX mZ
Th s vo ta c: m = 0,12*26 + 0,18*2 (0,06*30 +0,02*2) =1,64 gam.
Bi 2 [Khi A 2008] un nng hn hp kh gm 0,06 mol C2H2 v 0,04 mol H2 vi
xc tc Ni, sau mt thi gian thu c hn hp kh Y. Dn ton b hn hp Y li qua
bnh ng dung dch Brom d th cn li 0,448 lt hn hp kh Z ( ktc) c t khi
so vi O2 l 0,5. Khi lng bnh dung dch brom tng l bao nhiu
Gii
Da vo phng php gii trn ta c th gii nhanh chng c bi ny:
Khi lng bnh dung dch Br2 tng ln:
m =0,06*24 + 0,04*2 -
4,48
22,4
*0,5*32 =1,32 gam
Bi 3 [Khi A 2010] un nng hn hp X gm 0,02 mol C2H2 v 0,03 mol H2 vi
xc tc Ni, sau mt thi gian thu c hn hp Y. Dn ton b hn hp Y li t t
qua dung dch Br2 d th cn li 280 mL hn hp kh Z c t khi so vi H2 l 10,08.
Khi lng dung dch Brom tng ln l bao nhiu?
n
alkan
= n
H
2
O
- n
CO
2


36
Gii
Bi ny cng tng t nh bi khi A 2008 ta c th gii quyt nhanh chng
Khi lng bnh dung dch Br2 tng ln l:
m = 0,02*26 + 0,03*2 -
280
22,41000
*10,08*2 =0,328gam
Bi 4 Hn hp X gm C4H8 v H2 c t khi hi so vi H2 bng 10. Dn hn hp qua
Ni, t
0
thu c hn hp Y c t khi hi so vi H2 bng 14. Tnh hiu sut phn ng
cng H2.
Gii
p dng nh lut bo ton khi lng: mX =mY
Dng quy tc ng cho xc nh cht no ht trc khi tham gia phn ng
C4H8 56 18
20
H2 2 36
(1)
==
n
C
4
H
8
n
H
2
=
18
36
=
1
2
Alken s ht trc Hydro
Gi x l s mol C4H8 2x l s mol H2, a l s mol alken tham gia phn ng.
M
X
M
Y
=
n
Y
n
X
=
x+2x-u
x+2x
=
10
14
=
5
7

u
x
=
6
7
H% =
6
7
*100% =85,71%
Bi 5 Cracking hon ton hn hp 6,6 gam propan thu c hn hp A gm hai
hydrocarbon. Cho qua bnh cha 125mL dung dch Br2 c nng a mol/ L, dung
dch brom s b mt mu. Kh thot ra s c t khi hi so vi metan l 1,1875. Tnh a
Gii
Phn tch: Theo bi hn hp A cha hai kh hydrocarbon, vy hai hydrocarbon
l: C2H4 v CH4
Phng trnh phn ng cracking: C3H8
t
0
,P,xt
===== C2H4 +CH4 (1)

37
Kh A i qua dung dch brom th C2H4 b gi li, nu dd Br2 d th C2H4 phi ht, kh
thot ra l CH4, v hin nhin kh CH4 c t khi so vi CH4 bng 1 <1,1875
iu ny chng t C2H4 cn d v dd Br2 thiu
T nhng phn tch trn ta d dng gii quyt c bi ton ny mt cch nhanh
chng.
npropan =
6,6
44
=0,15 mol =netylen =nmetan
Dng phng php ng cho tm ra s mol kh thot ra
C2H4 28 3
19
CH4 16 9
T s ng cho ta nhn thy
n
C
2
H
4
n
CH
4
=
1
3

0,15-x
0,15
=
1
3
x = 0,1
Vy s mol C2H4 tham gia phn ng vi dd Br2 l 0,1 mol a =
0,1
0,125
=0,8mol/ L
Bi 6 Hn hp X gm 1 alkan v 1 alken. t chy hon ton X sn phm thu c
dn qua bnh ng nc vi trong d, thy bnh tng ln 7,98gam, v c 12 gam kt
ta. Tm khi lng hn hp X v cng thc phn t ca cc hydrocarbon. Bit rng
alkan chim 60% th tch ca hn hp.
Gii
Phn tch: Khi lng bnh dung dch nc vi trong tng ln chnh l khi lng
ca nc v kh CO2. Do bnh ng vi trong d nn s mol kh CO2 chnh bng s
mol CaCO3.
Da vo phng php gii nh trn ta c th nhanh chng tm ra c s mol alkan
tham gia phn ng t chy.
Theo bi ra ta c: n
CO
2
=
12
100
=0,12 mol m
H
2
O
=
7,98-0,1244
18
=0,15 mol
nalkan =0,15 0,12 =0,03 mol nalken =
0,4
0,6
* 0,03 =0,02 mol
p dng nh lut bo ton nguyn t: mX =mC +mH =0,12*12 +0,15*2 =1,74 gam

38
Gi n l s C trong alkan, m l s C trong alken (m 2). p dng nh lut bo ton
nguyn t C ta c:
0,03n +0,02m =0,12 (n, m nguyn)
Vy ch c gi n =2 v m =3 l cp nghim ph hp.
Cng thc ca alkan l: C2H6
Cng thc ca alken l: C3H6
Bi 7 Hn hp kh A gm H2 v olefin CnH2n c t l s mol l 3:2. un nng hn hp
A gm xc tc bt Ni c hn hp B, c t khi so vi H2 l 11,25. Hiu sut phn
ng l h%.
a. Lp biu thc tnh hiu sut ca h theo n
b. Bit h > 40% . Xc nh cng thc phn t ca olefin v h.
Gii
nalken <n
H
2
s mol phi tnh theo alken. Gi s trong hn hp kh A c cha 3 mol
H2 v 2 mol Alken.
Phng trnh phn ng: CnH2n + H2
N,t
0
=== CnH2n+2
Ban u: 2 3 (mol)
Phn ng: a a a
Sau phn ng: 2-a 3-a a
Hiu sut phn ng: h =
u
2
*100% (1) (h1)
Hn hp kh B c MB =11,25*2 =22,5 g/ mol =
m
E
n
E
=
m
A
n
E
=
14n2+23
2-a+3-a+a
=
28n+6
5-a

a =
71
15
-
28n
22,5
(2)
(1),(2)
==== h =
71
30
-
14n
22,5
(n2)
b/ Vi h >40% =0,4 th vo ta c 2,19 n < 3,16 n =3
Co ng thc olefin: C3H6 h = 50%
Bi 8 Hn hp X gm ankan v anken c t l s mol 3:2 .t chy hon ton X , dn
hi chy qua dd Ca(OH)2 bnh tng 7,8 g v c 8 g kt ta . Phn dd nc lc tc

39
dng vi Ca(OH)2 d xut hin thm 4 g kt ta na . Tm cng thc phn t mi
cht .
Gii
Phn tch: i vi dng bi ton ny ci kh l phn cho sn phm chy tc dng vi
dung dch Ca(OH)2. Ty vo t l s mol CO2 vi Ca(OH)2 m phn ng to ra mui
CaCO3 (trung ha), v mui Ca(HCO3)2 (mui acid). Phn ny xin cc bn c dnh
cht thi gian xem li bi u mc x l s liu khi cho CO2 tc dng vi Ca(OH)2.
Gi cng thc ca Alkan l CnH2n+2, Alken l CmH2m (n1, m2) (1)
Theo bi ra ta c:
n
aIRan
n
aIRen
=
2
3
nalkan =x (mol) nalken =1,5x (mol)
Khi lng dung dch tng ln: mb = m
CO
2
+m
H
2
O

CO2
Cu(0H)
2
====== _
CaCO
3
Ca(HCO)
2
Ca(OH)
2
====== CaCO3
p dng nh lut bo ton nguyn t n
C
(CO2) =n
C(HCO
3
-
)
+n
C(CO
3
2-
)

nC =
4
100
+
8
100
=0,12 mol
(1)
== m
H
2
O
=7,8 0,12*44 =2,52 gam
n
H
2
O
=
2,52
18
=0,14 mol nalkan =0,14 0,12 =0,02 mol nalken =0,03 mol
p dng n lut bo ton nguyn t C ta c: 0,02n +0,03m =0,12 2n + 3m = 12
Vy ch c n =3, m =2 l gi tr ph hp. C3H8 ; C2H4
Bi 9 Ly hai th tch bng nhau ca 1 anken th kh cho phn ng ring l vi
dung dch clo , brom . Khi lng ca hai sn phm cng khc nhau 44 ,5 g
a. Tnh th tch anken dng 27,3
0
C v 1 at . Gi s hiu sut p u t 80 %
b. Vit cng tha cu to c th c ca anken bit rng khi lng sn phm cng
brom thu c l 108 g v nu cho phn ng vi HCl ch thu c 1 sn phm duy
nht.
Gii

40
Phn tch: Dng ton ny l cho cng mt alken tham gia phn ng cng vi
halogen. i vi dng ny ta dng phng php tng gim khi lng gii quyt
bi ton. (cc bn xem li phn gio khoa phn phn ng cng halogen).
a. Bng kin thc sch gio khoa ta c th tnh nhanh ra s mol ra ca alken
nalken =
44,5
160-71
=0,5 mol. p dng phng trnh kh l tng: p.V =nRT
V =
nRT
p
=
0,5
22,4
23
(27,3+273)
0,1
=5,5 lt.
b. V th tch ca hai phn ca alken l nh nhau nn s mol ca alken bng
nhau.
(14n + 160)*0,5 = 108 n = 4 Alken: C4H8
V alken tc dng HCl to ra 1 sn phm, nn alken mang tnh i xng.
CH3 CH =CH CH3 :(Z) but 2 en.
Bi 10 Cho mt lng anken X tc dng vi nc c cht hu c Y , thy khi
lng bnh ng nc ban u tng 4,2 g .nu cho lng X nh trn tc dng vi
HBr thu c cht Z thy khi lng Y , Z khc nhau 9,45 g .Tm cng thc phn t
v gi tn X , gi s cc phn ng xy ra hon ton.
Gii
Phn tch: Bi ny cng tng t nh bi 9, c ngha rng dng phng php tng
gim khi lng gii quyt bi ny nhanh chng. (Cc bn c th tham kho thm
trong cun K Thut Gii Nhanh Ton Ha Hc - Dng Th - 2011, hiu thm
phn phng php tng gim khi lng, hoc cc sch vit v phng php ny).

+HBr CnH2n+1Br (Y)
CnH2n
+H2O CnH2n+1OH (Z)
Khi lng bnh nc tng ln chnh l khi lng ca alken malken =4,2 gam
p dng phng php tng gim khi lng d dng tnh ra c s mol alken (v
phn ng cng vi t l 1:1).

41
nalken =
m
Y
-m
Z
M
Y
-M
Z
=
9,45
81-18
=0,15 mol Malken =
4,2
0,15
=28 n = 2 C2H4 (etylen)
Bi 11 Hn hp kh A gm H2 v alken X. t chy 6 gam hn hp A thu c 17,6
gam kh CO2. Mt khc cho 6 gam A tc dng vi dung dch Brom d th thy c 32
gam Br2 tham gia phn ng. Tm cng thc ca X v tnh % th tch mi cht trong A.
Gii
Phn tch: Dng bi ton ny l s kt hp ca phn ng t chy v phn ng cng
halogenur. Alken t chy thu c CO2, H2O cng vi halogen vi t l 1:1 ta tm
c s mol alken (H2 khng tham gia vo phn ng cng Halogenur).
p dng nh lut bo ton nguyn t C (alken) ta c: n
CO
2
=nC (alken) =
17,6
44
=0,4 mol
Phn ng ca alken vi Br2: n
Br
2
=
32
160
=0,2 mol =nalken s Calken =
0,4
0,2
=2
Co ng thc phn t ca alken l: C2H4 n
H
2
=
6-0,228
2
=0,2 mol
%V
H
2
=%V
C
2
H
4
=50%
Bi 12 Hn hp X gm 1 alkan v 1 alken. Cho 1,68 lt hn hp X qua dung dch
Brom d, bnh brom tng ln m gam, kh thot ra c th tch 1,12 lt. Nu t chy
1,68 lt X ri dn sn phm qua nc vi trong d th c 12,5 gam kt ta. Cc kh o
c (ktc). Xc nh cc hydrocarbon trong X.
Gii
Phn tch: Dng bi ton t chy, bi ny ch cn lu : alkan khng tc dng vi
dung dch Brom.
Khi cho X tc dng vi dung dch Brom th alken b gi li, kh thot ra l alkan
bnh tng brom tng ln chnh l khi lng ca alken b gi li.
nalkan =
1,12
22,4
=0,05 mol nalken =
1,68
22,4
0,05 =0,025 mol.
Sn phm t chy X dn qua nc vo i trong d n
C0
2
=
1,25
100
=0,125 mol
Gi n l s C ca alkan (n1), m l s C ca alken (m2). p dng nh lut bo ton
nguyn t C trong X ta c: 0,05n +0,025m =0,125 2n + m = 5

42
Ch c n =1, m =3 l cp nghim ph hp CH4, C3H6 l cc hydrocarbon trong X.
Bi 13 Trong bnh kn cha c th tch l 5,6 lt cha 0,15 mol H2 v 0,1 mol C2H4
cng mt t bt Ni. Nung nng bnh mt thi gian ri lm lnh bnh n 0
0
C, p sut
trong bnh lc l p. Hn hp sau phn ng tc dng va vi 0,8 gam Br2 trong
dung dch. Tm % th tch H2 tham gia phn ng, tnh hiu sut phn ng hydro
ha v p sut p.
Gii
Phn tch: Bi ton ny lin quan n phn ng hydrogen ha alken (xem li
phng php gii), v c lin quan n phng trnh kh l tng.
Phng trnh hydro ha alken: CnH2n + H2
N,t
0
=== CnH2n+2
nalken <n
H
2
s mol phi tnh theo alken
V hn hp sau phn ng tc dng vi dung dch Br2 alken cn d
nalken d =n
Br
2
=
0,8
160
=0,005 mol nalken p =0,1 0,005 =0,095 mol =n
H
2
p

H =
0,095
0,1
100% =95% % V
H
2
=
0,095
0,15
*100% =63,33%
n
suu p
=0,1 +0,15 0,095 =0,155 mol p =
n
s
.R1
v
=
0,155
22,4
23
273
5,6
=0,62 atm
Bi 14 Hn hp A gm anken v hidro c t khi so vi hidro bng 9 ,dn hn hp i
qua bt niken nung nng n khi phn ng hon ton thu c kh B c t khi so
vi H2 bng 15 . Tm CTPT ca X v tnh % th tch ca kh trong A v B .
Gii
Phn tch: Bi ny dng phng php t chn lng cht v bo ton khi lng d
dng suy ra p n. Nhng ci kh l ta khng bit H2 hay alken ht dng bi ton
ny nh mnh vo yu t gia hai cht phn ng ci no ht, ci no d.
Gi s trong hn hp A cha 1 mol hn hp kh gm alken v H2 (t chn lng
cht) nA =1 mol
p dng nh lut bo ton khi lng ta c: mA =mB
M
X
M
Y
=
n
Y
n
X
=
9
15
=
3
5
nY =0,6

43
Trng hp 1: Alken d v H2 tham gia phn ng ht (v phn ng xy ra hon
ton H = 100%).
n
H
2
p
=nX nY =1 0,6 =0,4 mol =n
H
2
b
nalken =1 0,4 =0,6 mol
MX =14n.0,6 +2.0,4 =9.2 =18 n = 2,048 loi (v n nguyn)
Trng hp 2: Alken ht v H2 d nalken =0,4 mol n
H
2

=0,6 mol
MX =14n.0,4+2.0,6 =9.2 =18 n = 3 (tha mn) CTPT alken: C3H6
% I
C
3
H
6
=40% % I
H
2
=60%.
Bi 15 Mt hn hp gm 3 anken C3H6,C4H8 , C5H10 . Nu t chy hn hp cho 6,72 l
hi nc (ktc) . Nu cho hn hp phn ng vi hydro d c xc tc, t chy sn
phm ri dn sn phm chy vo nc vi trong d , th khi lng kt ta sinh ra
l bao nhiu.
Gii
Phn tch: Bi ton ny thc cht l ly 3 alken trn em t chy ri dn vo nc
vi trong d hi c bao nhiu gam kt ta. Mc ch a ra bi ton ny nhm nhc
li mt ln na: Trong hu c phng php mnh gii ton l phng php bo
ton khi lng v nguyn t.
Cn lu : phn ng t chy alken lun c: n
CO
2
=n
H
2
O

Vy t nhng phn tch trn bi ton ny gii mt cch d dng: p dng nh lut
bo ton nguyn t C trong hn hp Alken: n
CO
2
=nC =n
H
2
O
=
6,72
22,4
=0,3 mol =n
m = 0,3.100 = 30 gam


44
BI 5 ALKADIEN (CnH2n-2) (n4)
A. KIN THC C BN
I. L TNH
Hai alkadien quan trng nghin cu THPT l:
Butadien -1,3 (ivinyl) l cht kh khng mu, c mi c trng
CH2 =CH CH =CH2 cht kh, t
s
0
=- 4
0
C.
Isopren (2 metylbutadien 1, 3): l cht lng khng mu, si 34
0
C.
CH2 =C CH =CH2 (Isopren)
CH3
u l nhng cht tan rt t trong nc v tan c trong mt s dung
mi phn cc
II. HA TNH
1. Phn ng cng (H2, X2, HX)
a. Cng ti a theo t l s mol 1:2
CH2 =CH CH =CH2 +2Br2
b. Cng theo t l 1:1
Phn ng cng theo t l 1:1 nh hng theo hai hng cng theo 1,2 v
nh hng cng theo 1,4. Cl
(1,2)
CH3 CH CH =CH2
CH2 =CH CH =CH2 +HCl

CH3 CH =CH CH2 - Cl
(1,4)
2. Phn ng trng hp
Trng hp (1,4) cho polymer n hi (cao su nhn to)
n(CH2 =CH CH =CH2)
Nu,xt,p
=====(-CH2 CH =CH CH2)n
cao su Buna
nCH2 =C-CH=CH2
Nu,xt
==== (- CH2 C=CH-CH2 -)n
CH3 CH3
Cao su isopren


45
nCH2=C-CH=CH2
Nu,xt
==== (-CH2-C-CH CH CH2-)n
Cl Cl
III. IU CH
1. iu ch Butadien 1,3
a. ehydro ha
Butadien 1,3 c iu ch bi qu trnh dehydro butan hoc buten
nhit cao (600
0
C) c mt cht xc tc (Cr2O3)
C4H10
Cr
2
O
3,t
0
======C4H6
C4H8
xt,t
0
=== C4H6
b. Dehydro ho v dehydrat ha t ru etylic nh xc tc MgO/ Al2O3 nhit
400
0
C 500
0
C.
2CH3CH2OH
MgO/ AI
2
O
3
,450
0
C
=============C4H6 +H2 +2H2O
c. i t acetylen
CHCH
CuCI/ NH
4
CI,150
0
C
============== CH2 =CH C CH
+H
2
,Pd
===== C4H6
d. Dehydrat ha butadiol 1,3 hoc butadiol 1,4
CH3 CH CH2 CH2 C4H6 + 2H2O
OH OH
e. Tng hp theo Konbe (c)
2CH2=CH-COONa +H2O
xt
CH2 =CH CH =CH2 +2CO2 +2NaOH +H2
2. iu ch Isopren
a. Dehydro ha isopentan v isopenten (t du m)
CH3 CH CH2 CH3
xt
CH2 =C CH2 CH2 CH3
xt
CH2 =C -CH =CH2
CH3 CH3 CH3
b. i t propen
CH2=CH
xt
CH2=C CH2-CH2-CH3
xt
CH2=C CH =CH2
CH3 CH3
IV. CAO SU TNG HP
Cao su tng hp l cht do c con ngi ch to vi chc nng l cht co
gin. Mt cht co gin l vt cht c c tnh c hc l chu c sc p thay i hnh

46
dng hn phn ln cc vt cht khc m vn phc hi hnh dng c. Cao su tng hp
c dng thay th cao su t nhin trong rt nhiu ng dng, khi m nhng c tnh
u vit ca n pht huy tc dng.
Cao su t nhin c ngun gc t nha cy cao su, tri qua phn ng trng hp
to thnh isopren vi i cht tp chp. iu ny gii hn cc c tnh ca cao su.
Thm vo , nhng hn ch cn t l cc lin kt i khng mong mun v tp
cht ph t phn ng trng hp m cao su t nhin. V nhng l do trn, cc ch s
c tnh ca cao su t nhin b suy gim t nhiu mc d qu trnh lu ha c gip
ci thin tr li.
Cao su tng hp c to ra t phn ng trng ngng cc cu trc n bao gm
isopren (2-methyl-1,3-butadien), 1,3-butadien, cloropren (2-cloro-1,3-butadien) v
isobutylen (methylpropen) vi mt lng nh phn trm isopren cho lin kt chui.
Thm vo , cc cu trc n ny c th trn vi cc t l mong mun to phn
ng ng trng hp m kt qu l cc cu trc cao su tng hp c cc c tnh vt l,
c hc v ha hc khc nhau.
T nhng nm 1890, khi cc phng tin giao thng ng b s dng bnh hi ra
i, nhu cu cao su tng ln rt nhanh. Cc vn chnh tr khin cho gi cao su t
nhin dao ng rt ln. Ngun cung thiu ht, c bit l trong nhng nm chin
tranh a n nhu cu phi to ra cao su tng hp.
Nm 1879, Bouchardt ch to c mt loi cao su tng hp t phn ng trng hp
isopren trong phng th nghim. Cc nh khoa hc Anh v c sau , trong thi
gian 1910-1912, pht trin cc phng php khc cng to ra cht do t isopren.
c l quc gia u tin thnh cng trong vic sn xut cao su tng hp quy m
thng mi. Vic ny din ra trong Th chin th nht, khi nc ny khng tm
ngun cao su t nhin. Cao su tng hp ny c cu trc khc vi sn phm ca
Bouchardt, n da trn s trng hp butadien l thnh qu ca nghin cu trong
phng th nghim ca nh khoa hc Nga Sergei Lebedev. Khi chin tranh chm dt,
loi cao su ny b thay th bng cao su t nhin, mc du vy cc nh khoa hc vn
tip tc cng cuc tm kim cc cht cao su tng hp mi v cc quy trnh sn xut
mi. Kt qu ca nhng n lc ny l pht minh ra cao su Buna S (Cao su styren-
butadien). y l sn phm ng trng ngng ca butadien v styren, ngy nay, n
chim mt na sn lng cao su tng hp ton cu.
Cho n nm 1925, gi cao su t nhin tng n ngng m rt nhiu cng
ty bt u tm kim cc phng php sn xut cao su nhn to nhm cnh tranh vi
sn phm thin nhin. M, qu trnh tm kim tp trung vo cc nguyn liu khc
vi nhng g ang c nghin cu Chu u. Hng Thiokol bt u bn cao su
tng hp Neoprene nm 1930. Hng DuPont, da trn kt qu nghin cu trong
phng th nghim Nieuwland cng tung ra th trng loi cao su tng t nm
1931.


47
BI 6 ALKIN (CnH2n-2) (n 2)
A. KIN THC C BN
I. L TNH
Dng tn ti ca alken iu kin thng:
Th kh tng ng vi: n =2 4
Th lng tng ng vi n =5 18
Th rn n 19
Rt t tan trong nc tan c trong mt s dung mi hu c
II. HA TNH
1. Phn ng oxy ha
a. Phn ng oxy ha hon ton
Alkin chy sinh ra kh CO2 v hi nc km theo nhit lng ta ra .
CnH2n-2 +
3n+1
2
O2 nCO2 + (n-1)H2O +Q
Phn ng t chy ca Alkin lun c:

n
CD
2
< n
H
2
D

H qu:

b. Oxy ha khng hon ton
Alkin cng ging nh alken, phn t d b ct t ti v tr ni ba do
nhng tc nhn oxy ha mnh nh: Ozon, hoc KMnO4. V ni ba km
hot tnh hn ni i, do hiu sut cc sn phm c c do s ct
t hn thng thp hn alken.
V d: 3C2H2 +8KMnO4 3K2C2O4 +8MnO2 + 2KOH + 2H2O
2. Phn ng cng
a. Cng H2
Phn ng xy ra theo hai giai on
CnH2n-2
Pd/ PbCO
3
======= CnH2n
NI,t
o
=== CnH2n+2
b. Cng halogen
Phn ng cng ca alkin xy ra theo hai giai on, giai on sau s
xy ra kh khan hn giai on u.
CnH2n-2
+X
2
=== CnH2n-2X2
+X
2
===CnH2n-2X4
nAlkin =n
CD
2
- n
H
2
D


48
Nhn xt: Alkin cng lm mt mu dung dch Brom nhng thng xy
ra chm hn alken.
c. Phn ng cng HX
Phn ng cng HX xy ra theo hai giai on, giai on sau thng
xy ra kh khn hn giai on u.
Phn ng cng tun theo quy tc Markovnikov Cl
V d CHC CH3 + HCl CH2 =C CH3
+HCI
=== CH3 C CH3
Cl Cl
d. Cng H2O (hydrat ha)
Axetylen tc dng vi nc to ra aldehid
C2H2 + H2O
HgS0
4
,t
0
=80
0
C
============ CH3CHO (Aldehid acetic)
Cc ng ng ca axetylen phn ng vi nc sinh ra ceton
R - CC R +H2O
Xt,t
0
===

e. Cng acid
Acetylen tc dng vi acid acetic to vinylacetat di s xc tc ca
km acetat
CH CH + HOOCCH3
Zn(CH
3
COO)
2
========== CH2=CHOOCCH3
1ng hp
======== (CH2 CH-)n
OCOCH3
Poly Vinyl Acetat (P.V.A)
f. Phn ng th vi cc ion kim loi nng ha tr I (Ag
+
, Cu
+
)
Phn ng ny ch xy ra cho cc alkin c ni ba u mch, phn ng ca
acetylen v cc alkin -1 tc dng vi dung dch AgNO3 / NH3 cho kt ta
mu vng v tc dng vi dung dch CuCl/ NH3 cho kt ta mu .
V d:
CHCH + 2AgNO3 +NH3 AgCCAg + NH4NO3
(vng nht)
R - CCH + AgNO3 +NH3 R C CAg + NH4NO3
CHCH + 2CuCl + NH3 CuC CCu + NH4Cl
()
Nhn xt:
Phn ng ny dng nhn bit alkin u mch.
Phn ng ny dng nhn bit alkin vi cc hydrocarbon khc

49
Theo phng trnh phn ng ta nhn thy

g. Phn ng trng hp
Acetylen c cc phn ng sau y:
Phn ng nh hp:
2CHCH
Xt,t
0
===CH=CH-CCH
Phn ng tam hp
3CHCH
600
0
,C
=====C6H6 (benzen)
Phn ng trng hp
nCHCH (CH2)n (nha Cupren).
3. Tnh acid
Hydrogen ni vi carbon ca ni ba trong cc hp cht acetylen v
alkin cui dy c tnh acid. Trong tt c cc alkin u mch th acetylen
l alkin c tnh acid mnh nht.
V d:
HCCH + Na NaCCNa + H2
III. IU CH
1. iu ch Acetylen
Than a Than cc
CaC2 C2H2
a vo i CaO
Trong k ngh du kh acetylen cn c tng hp bng s oxid ha
metan nhit 1500
0
C
6CH4 + O2
1500
0
C
===== 2CHCH + 2CO +10H2
T C v H2
C + H2
h quang In
========== C2H2
iu ch t cc mui acetylenur
AgCCAg + 2HCl HCCH + 2AgCl
2. iu ch cc dy ng ng ca acetylen
Phn ng ehydro ha alkan v alken.
CnH2n+2
Xt,P,t
0
===== CnH2n
Phng php tng mch Carbon
Ag - CC R +RCl
Xt,t
c
=== R C C R +AgCl
nacetylen =2.nAg+ = n nng ng =nAg+ =n

50
i t dn xut ihalogen

+KOH
Lt0H
==== R1 - CC-R2 +2KCl +H2O

B. PHNG PHP GII TON
VN 1: PHN NG TH CA ALKIN VI CC KIM LOI NNG (Ag
+
, Cu
+
)
PHNG PHP
Ch c cc Alkin u mch tc dng c vi dung dch AgNO3/ NH3
(CuCl/ NH3).
i vi acetylen phn ng vi AgNO3/ NH3 lun cho t l:

i vi cc ng ng c ni ba u mch lun c:

Lp t s T =
n
aIRn
n

+Nu 0 <T <1: Trong hn hp c cha acetylen
+T =1: trong hn hp khng c cha acetylen
VN 2: PHN NG CHY CA ALKIN
PHNG PHP
Phn ng t chy:
CnH2n-2 +
3n+1
2
O2 nCO2 + (n-1)H2O
Phn ng t chy alkin lun cho

t chy hn hp alken v alkin lun c:

n
C
2
H
2
=2n
Ag
+ = 2n
nalkin =n
Ag
+ = n
n
CO
2
<n
H
2
O

nalkin =n
CO
2
- n
H
2
O

nalkin =n
CO
2
- n
H
2
O


51
VN 3: PHN NG CNG H2
PHNG PHP
Cc bn xem li phn phng php gii ca alken
y cn ch vn dng linh hot nh lut bo ton khi lng
VN 4: PHN NG CNG Br2
PHNG PHP
Phn ng tng qut ca hydrocarbon khng no ni chung v alkin ni ring:
CnH2n+2-2k +kBr2
xt
CnH2nBr2k (k l s lin kt )
T phn ng ta c nhn xt quan trng:

C. BI TP
Bi 1 Trn 28,2 gam mt hn hp gm 3 hydrocarbon lin tip thuc dy ng ng
ca acetylen vi mt lng d H2 ri thi qua mt ng Ni t nng phn ng xy
ra hon ton, th tch ca hn hp sau phn ng gim i 26,88 lt (ktc). Xc nh
cng thc ca 3 hydrocarbon trn.
Gii
Phn tch: bi ni rt r l 3 hydrocarbon trn thuc dy ng ng ca
acetylen (CnH2n-2). Mu cht ca bi ton ny l hn hp kh gim sau phn ng
chnh s gim ca kh H2. V alkin tc dng vi H2 vi xc tc Ni to alkan theo t l
1:2 nn d dng suy ra c s mol alkin.
Gi cng thc phn t tng ng cho 3 hydrocarbon trn l: C
n
H
2n-2
(n2)
T phn tch trn ta c th tnh c s mol ca 3 hydrocarbon:
nhh =
1
2

26,88
22,4
=0,6 mol Mhh =
28,2
0,6
=47 g/ mol 14n 2 =47 n =3,5
Theo tnh cht gi tr trung bnh ta c 2 cp nghim ph hp vi bi ton:
Cp nghim 1: C3H4, C4H6, C5H8; Cp nghim 2: C2H2, C3H4, C4H6.
k =
n
E
2
n
hydocabon


52
Bi 2 Trong bnh kn th tch l 6,72 lt (ktc) cha hn hp gm hydrocarbon A v
H2 nung nng vi xc tc l Ni a v nhit ban u, p sut trong bnh l p, thu
c 1 kh B duy nht c t khi hi so vi hn hp ban u bng 3. t chy B thu
c 8,8 gam CO2 v 5,4 gam H2O. Xc nh CTPT ca A v p.
Gii
Phn tch: Bi ton ny dng nh lut bo ton nguyn t C d dng tm ra c
CTPT ca A. Mc ch a ra bi ton ny khng phi xc nh CTPT ca A m ci
chnh l n tp li mt s nh lut kh.
Phng trnh kh l tng: pV =nRT (vi R =
22,4
273
=0,082)
trng thi 1,2 ng vi: p1, T1, V1, n1; p2, T2, V2.
p dng phng trnh kh l tng: p1V1 =n1RT1
p2V2 =n2RT2
iu kin ng nhit v ng p:
V
1
V
2
=
n
1
n
2

iu kin ng tch v ng nhit

Bi ton ni rt r l sau phn ng ca hydcarbon A vi hydrogen thu c kh B
l duy nht A l hp cha no H2 tham gia phn ng va vi A B l Alkan
nhh =
6,72
22,4
=0,3 mol; n
CO
2
=
8,8
44
=0,2 mol; n
H
2
O
=
5,4
18
=0,3mol
nB =n
H
2
O
- n
CO
2
=0,3 0,2 =0,1 mol =nA n
H
2
=0,3 0,1 =0,2 mol
S CA =
n
CO
2
n
A
=
0,2
0,1
=2; S lin kt A =k =
n
H
2
n
A
=
0,2
0,1
=2 CTPT ca A l C2H2
V iu kin ng tch v ng nhit ta p dng cng thc nh phn tch trn
p
1
p
2
=
n
1
n
2
= 3 p2 =
1
3
p1 =
1
3
(atm). (Gi s hn hp ban u c p sut p =1atm)

p
1
p
2
=
n
1
n
2


53
Bi 3 Mt hn hp kh gm H2, 1 olefin, v 1 ng ng ca acetylen. Cho 135mL
hn hp kh i qua Ni nung nng th sau phn ng cn li 60mL mt hydrocarbon no
duy nht. Mt khc t chy hon ton 60mL hn hp th thu c 180mL kh CO2.
Bit cc th tch kh o cng iu kin. Xc nh cng thc hai hydrocarbon v
thnh phn phn trm khi lng hn hp kh trn.
Gii
Phn tch: V hn hp sau khi nung nng thu c ch duy nht mt hydrocarbon
no duy nht Olein v alkin c cng s C Tng s mol ca H2 bng tng s mol
ca hai hydrocarbon.
Cch 1 (Dng phng php thng thng)
Nh phn tch trn th ta gi CTPT ca olefin l CnH2n v ca alkin l CnH2n-2 (n2)
Gi x, y, z ln lt l th tch ca olefin, alkin v H2.
Phng trnh phn ng: CnH2n +H2 CnH2n+2
x x x
CnH2n-2 +2H2 CnH2n+2
y 2y y
Theo bi ra ta c: x +y +z =135 (mL)
z =x+2y (mL) x = 45 (mL), y = 15 mL, z = 75mL
x +y =60 (mL)
Phn ng chy: CnH2n +
3n
2
O2 nCO2 +nH2O
x nx
CnH2n-2 +
3n-1
2
O2 nCO2 +(n-1)H2O
y ny
V
CO
2
=n(x+y) =180mL 60n = 180 n =3 Olein: C3H6; alkin: C3H4
%m
H
2
=5,68% ; %m
C
3
H
6
=71,68%; %m
C
3
H
4
=22,72%

54
Cch 2 V hn hp trn c s C l nh nhau, nn gi CTPT tng ng cho hai
hydrocarbon trn l: C
n
H
2n+2-2k
vi th tch l a
Phng trnh phn ng: C
n
H
2n+2-2k
+k H2 CnH2n+2
a ka a
Theo bi ra ta c: a +ka =135mL ; Alkan c th tch a =60mL ka =75mL
Phn ng t chy Alkan:
CnH2n+2 +
3n+1
2
O2 nCO2 +(n+1)H2O
a na
Th tch kh CO2 thot ra: na =180 n = 3 Olefin: C3H6; alkin: C3H4
Vn dng tnh cht gi tr trung bnh trong lin kt
k =
2x+
(x+)
=
75
60
=
5
4
x = 45 y =15 (mL)
%m
H
2
=5,68% ; %m
C
3
H
6
=71,68%; %m
C
3
H
4
=22,72%
Bi 4 Hn hp A gm propin v 1 ng ng trn theo t l mol l 1:1 . Cho 0,672 lt
hn hp A (ktc) tc dng va ht vi 45mL dung dch AgNO3/ NH3 1M. Tm cng
thc phn t ca alkin cn li.
Gii
Phn tch: S dng phng php gii trn ta lp t l: T =
n
AIRn
n
Ag
+

T l ny c: 0 <T <1 : Khng nh ngay trong hn chc chn c cha acetylen
n
Ag
+ =0,045.1 =0,045 mol; nA =
0,672
22,4
=0,03 mol T =
0,03
0,045
=
2
3
<1
CTPT ca alkin cn li: C2H2
Bi 5 Khi nung 15,68 lt CH4 (ktc) trong mt bnh kn th thu c 26,88 lt (ktc)
hn hp kh A gm CH4, C2H2, C2H4, H2. Nu cho hn hp kh A i qua nc Brom th
nc Brom b nht mu, thu c hn hp kh B c phn t gam trung bnh
32
9
. Nu
cho hn hp kh A i qua Pt nung nng th thu c hn hp kh C. Bng phng

55
php thch hp, t hn hp C tch thnh hai hn hp C1 v C2, trong C1 gm cc
kh khng lm mt mu dung dch Brom, c khi lng ln hn C2 l 0,48 gam. Hn
hp C2 c phn t gam trung bnh 26,8. Tnh thnh phn phn trm theo phn t
gam cc kh trong hn hp C.
Gii
Phn tch: Trc ht l bi ton ny qu di, khin cho cc bn c cm thy c
ch bi v bi ton ch. Nu bi ton ch th ta nn phn tch theo dng s
tm tt cho d nh. Th hai bi ton ny l bi ton vn dng kin thc tng hp
v hydrocarbon m chng ta hc. Do vy gii quyt bi ton cn vn dng tt
c kin thc tng hp gio khoa m ta hc. Bi ny ni chung l kh, ni chung
khng kho lo d b tc gi nh la cho nn chng ta phi ht sc bnh tnh
i ph. Bi ny ti xin gii thch k tng bc v sao li ra nh th (xin qu c
gi lng th v s c nhiu ngi ni l khng cn thit. Nhng mc ch ca ti
a n cho cc em hc sinh hiu thm (c bit l nhng em cha hiu) nm bt r
c v sao li ra nh th? V ti sao li ra nh vy?
Tm tt
15,68 lt CH4
t
0
C
==hh A: 26,88 lt _
H
2
C
2
H
2
C
2
H
4
CH
4

+ Br
2
==== B (M
B
=
32
9
) _
CH
4
H
2

Pt
C _
C
1
hhng mt mu Br
2
C
2
: M
C
2
=26,8
(m
C
1
m
C
2
=0,48 g)
Nhn thy rng s mol nA =
26,88
22,4
=1,2 mol; n
CH
4
=
15,68
22,4
=0,7 mol. Sau phn ng ca
CH4 vi nhit ta nhn thy s C trong A tng ln nhng khi lng ca chng khng
i (bo ton khi lng) so vi ban u. T nhng nhn xt ta c mt cng
thc: n
CH
4 b
=2(n
C
2
H
2
+n
C
2
H
4
) +n
CH
4 d
=0,7mol (1)
Phn tch: V sao li ra cng thc (1)? (s c nhiu bn t cu hi ny)
Nh chng ta c qua kin thc gio khoa phn iu ch acetylen t Mtan:
2CH4
1500
0
C
===== C2H2 +3H2 (I)

56
2CH4
t
0
C2H4 +2H2 (II).
Thy ngay iu ny nh bo ton nguyn t C th c th suy ra c cng thc nh
trn.
Mt khc: nA =n
H
2
+n
C
2
H
2
+n
C
2
H
4
+n
CH
4
d
=1,2 mol (2)
Theo phng trnh (I), (II) ta nhn thy rng: n
H
2
=3n
C
2
H
2
+2n
C
2
H
4
(3)
Hn hp B: cha H2 v CH4 d dng quy tc ng cho ta d dng tm ra c mi
lin h ca s mol n
H
2
v n
CH
4
d
.
CH4 16
14
9

MB =
32
9
n
H
2
=8n
CH
4
d
(4)
H2 2
112
9

Gii (1), (2), (3), (4) : n
H
2
=0,8 mol, n
CH
4
d
=0,1 mol =n
C
2
H
4
, n
C
2
H
2
=0,2 mol
p dng nh lut bo ton khi lng: mA =mC =m
CH
4 b
=0,7.16 =11,2 gam
Mt khc mC =m
C
1
+m
C
2
=11,2 (*) kt hp vi m
C
1
m
C
2
=0,48 g (**)
Gii ra ta c m
C
1
=5,68 gam gm: C2H6, H2 v m
C
2
=5,36 gam gm C2H2, C2H4.
m
C
2
=5,36 =24n
C
2
H
2
+28n
C
2
H
4
(***)
Dng quy tc ng cho ta c th tm ra mi lin h s mol ca C2H2 v C2H4.
C2H2 26 1,2
M
C
2
=26,8 n
C
2
H
2
=1,5n
C
2
H
4
(****)
C2H4 28 0,8
T (***), (****) gii ra ta c n
C
2
H
2
d
=0,12mol, n
C
2
H
4 d
=0,08 mol
n
C
2
H
2
p =0,2 0,12 =0,08 mol; n
C
2
H
4
=0,1 0,08 =0,02 mol
n
C
2
H
6 to thnh

=0,08 +0,02 =0,1 mol n
H
2
d
=0,8 - 0,02 2. 0,08 =0,62 mol

57
n
C
=0,1 mol +0,62 mol+0,08mol +0,12mol +0,1mol =1,02mol.
%V
H
2
=
0,62
1,02
*100% =60.78% ; %V
C
2
H
6
=
0,1
1,02
*100% =9,80% =%V
CH
4

%V
C
2
H
4
=
0,08
1,02
*100% =7,84% ; %V
C
2
H
2
=
0,12
1.02
*100% =11,76%
Bi 6 t chy hon ton hn hp 2 kh hydrocarbon ng ng X (c th tch 2,24
lt 0
0
, 1at) v Y hp th ton b kh CO2 bng dung dch Ba(OH)2 d c 133,96g
kt ta. Xc nh cng thc cu to ca X,Y, bit s mol cng nh s nguyn t
Carbon xa X nh hn Y v hn hp X,Y to vi dung dch Cu
+
trong NH4OH
13,68gam kt ta mu . Tnh hiu sut phn ng bit n phi trn 70%.
Gii
Phn tch: V X, Y u tc dng c vi Cu
+
trong NH4OH X, Y u c th cha ni
ba u mch. (C th c X v Y u tc dng c vi Cu
+
hoc ch c X hoc Y tc
dng c vi Y). Gi nY l s mol ca Y v n, m l s C ca X v Y.
Theo bi ra ta c: _
y >0,1
m>n
n 2,m 3

nX =
2,24
22,4
=0,1 mol; n
CO
2
=
133,96
197
=0,68 mol =0,1n +ym y =
0,68-0,1n
m
>0,1
5 m+ n < 6,8 (n,m Z) ]
n+m=5
n+m=6

Vi n +m =5 n = 2 v m =3 cp nghim alkin: C2H2 v C3H4
Vi n +m =6 n = 2 v m =4 Cp nghim alkin: C2H2 v C4H6
Cch 1
Trng hp 1 Vi cp nghim C2H2 v C3H4 HCCH, HCC-CH3 t suy ra
c: y =0,16 mol
Vit nhanh phn ng vi Cu
+
ta c kt ta ca cc alkin vi ng nh sau:
2Cu
+
+HCCH CuCCCu
Cu
+
+HCC-CH3 CuCC-CH3
m = 148.0,1 + 103.0,16 = 31,28 gam H% =
13,68
31,28
*100% =43,73% <70% (loi)

58
Trng hp 2 Vi cp nghim C2H2 v C3H4 t suy ra c: y =0,12 mol
Kh nng 1: X, Y u tc dng c vi Cu
+
Y co cu to: HC C-CH2-CH3
m = 0,1*148 + 0,12*117 = 28,84 gam H% =
13,68
28,84
*100% =47,43 <70% (loi)
Kh nng 2: Y khng tc dng c vi Cu
+
Y co cu to: H3C-CC-CH3
m = 152*0,1 = 15,2 gam H% =
13,68
15,2
*100% =90% (tha mn)
Vy X l C2H2 v Y l C4H6 c CTCT: H3C-CC-CH3
Cch 2 (Gii quyt bi ton bng phng php suy lun)
Da vo tnh cht ca hiu sut: H =
Ing thc t
Ing I thuyt
*100%>70%
ml thuyt <
13,68
70
100 =19,54 gam mY < 19,54 -13,68 =5,86g iu ny ch
ng khi Y khng tc dng c vi Cu
+

cp nghim ph hp ch c th X l C2H2 v Y l C4H6 c CTCT: H3C-CC-CH3
Bi 7 t chy hon ton hydrocarbon A mch h thu c s mol CO2 gp 2 ln s
mol H2O. Mt khc, nu ly 0,1 mol A tc dng vi dung dch AgNO3/ NH3 d thu
c 15,9gam kt ta. Tm cng thc ca A.
Gii
V t chy A thu c s mol n
CO
2
=2n
H
2
O
v A tc dng c vi AgNO3 nn chc
chn A c ni ba u mch. (Lu ta khng c khng nh l Alkin).
Gi cng thc phn t tng qut ca A l CxHx (v theo gi thit n
CO
2
=2n
H
2
O
).
Da vo khi lng sn phm to thnh ca A tc dng vi AgNO3, ta nhn thy rng
A khng th cha hai ni ba u mch, bi v nu c hai ni ba u mch th lc
khi lng ca Ag c trong sn phm l 2.108.0,1 =21,6gam >15,9 gam.
Phng trnh phn ng vi AgNO3/ NH3:
CxHx + Ag
+
CxHx -1Ag
13x + 107 =
15,9
0,1
=159 x = 4 CTCT A: C4H4 HCC-CH=CH2.


59
Bi 8 Hn hp Z c 0,15 mol CH4, 0,09 mol C2H2 v 0,2 mol H2. Cho hn hp Z i qua
bnh ng mt t bt Ni nung nng, c hn hp Y, sau dn hn hp Y qua bnh
ng nc Brom d, thy bnh brom tng ln 0,82gam. Hn hp kh T thot ra c t
khi hi so vi H2 l 8. Tnh s mol mi cht trong T.
Gii
Phn tch: Dng bi ton ny trnh by rt k phn phng php gii ton
Alken. Cc bn dnh cht thi gian n li bi c vi 2 mc ch:
+Th nht: Cng c li kin thc, nm vng v su hn
+Th hai: Nhm to cho cc bn mt thi quen xem li bi trc khi chuyn sang
bi mi.
Hn hp Z c: mZ =0,15*16 +0,09*26 +0,2*2 =5,14 gam =mY
Khi lng bnh brom tng ln chnh l khi lng ca cc Hydrocarbon cha no.
m(C2H2, C2H4) =0,82 gam mT =5,14 0,82 =4,32 gam.(CH4, C2H6, H2)
Lu : S mol ca CH4 trc v sau lun khng i v bng 0,15 mol
nT =
4,32
8.2
=0,27 mol n
H
2
+n
C
2
H
6
=0,27 0,15 =0,12 mol (1)
Mt khc mT =m
H
2
+m
C
2
H
6
+0,15*16 =4,32 m
H
2
+m
C
2
H
6
=1,92g (2)
Gii (1), (2) ta c n
H
2
=n
C
2
H
6
=0,06 mol
hn hp Z gm _
0,06 mol H
2
0,06 mol C
2
H
6
0,15 mol CH
4

Bi 9 t chy hn hp A gm hai hydrocarbon mch h X, Y cng dy ng ng,
sn phm thu c, dn qua bnh ng dung dch 105mL Ba(OH)2 2M thu c 39,4
gam kt ta v dung dch B c khi lng nh hn khi lng dung dch Ba(OH)2
ban u l 27,38 gam. Dung dch B un nng thy c khi lng kt ta. Tm cng
thc ca X, Y bit rng nX =
4
9
nA. Tm khi lng X, Y trong A.
Gii

60
Phn tch : bi ni rt r v ta c th khng nh c ngay : CO2 tc dng vi
dung dch Ba(OH)2 thu c hai mui. tm c dy ng ng ca X, Y ta phi
da vo s so snh ca s mol CO2 v H2O. Mu cht bi ton l lm sao tm c
mi lin h ny. Da vo s tng gim khi lng dung dch B so vi Ba(OH)2 ban
u, v khi lng kt ta to thnh. y bi ton khng ni r X, Y l s Carbon
ca X hay Y ln nn chng ta phi xt tng trng hp. T nhng phn tch trn
chng ta s tin hnh gii quyt bi ton mt cch nhanh chng.
Sn phm t chy dn qua bnh ng dung dch Ba(OH)2 to ra hai mui :
Ba(OH)2 +CO2 BaCO3 + H2O
x x x
Ba(OH)2 +2CO2 Ba(HCO3)2
y 2y y
Theo bi ra ta suy ra c x, y _
x +y =0,21
x =
39.4
197
=0,2
x = 0,2 mol, y = 0,01 mol
n
CO
2
=x +2y =0,2 +2*0,01 =0,22 mol ( 1)
Lu : m c im mu cht bi ton ny, cc bn nn c li phng php
gii ton bi u tin. S rt c ch cc bn rt nhiu.
Theo bi : mdd B +27,38 =m
dd(BaOH)
2
m
CO
2
+m
H
2
O
m + 27,38 = 0
m
CO
2
+m
H
2
O
=12,02 gam (2)
(1),(2)
==== m
H
2
O
=2,34 gam n
H
2
O
=0,13 mol.
n
CO
2
>n
H
2
O
X, Y thuc dy ng ng ca alkin, hoc alkadien c CTPT : CnH2n-2
nA =n
CO
2
- n
H
2
O
=0,22 0,13 =0,09 mol n =
0,22
0,09
=
22
9

V CTPT ca alkadien mun tn ti phi c n 4 X, Y l dy ng ng ca alkin.
Trng hp 1: X l C2H2 vi s mol l 0,04 mol (v nX =
4
9
nA) nY =0,05 mol
0,04*2 + 0,05n = 0,22 n = 2,8 (loi)
Trng hp 2: Y l C2H2 vi s mol l 0,05 mol 0,04*n + 0,05*2 = 0,22 n =3

61
Vy X l C3H4 v Y l C2H2 vi khi lng X, Y l :
_
m
C
2
H
2
=0,05 26 =1,3 gam
m
C
3
H
4
=0,04 40 =1,6 gam

Bi 10 Cho hn hp kh A (ktc) gm hai hydrocarbon mch thng X, Y. Ly 322,56
mL hn hp A cho t t qua dung dch Br2 d thy c 3,84 gam Br2 tham gia phn
ng. Sau phn ng khng thy kh thot ra khi dung dch. Mt khc t chy hon
ton 322,56mL A thu c 1,6896 gam CO2 . Tm cng thc phn t ca X, Y.
Gii
Phn tch : Dng bi ton kt hp tnh cht ca Hydrocarbon cha no, phn ng
cng v phn ng t chy. Bi ny ta nn gi cng thc tng ng ca X, Y (hay
cn gi l CTPT trung bnh). gii bi ny ta vn dng trit phn tnh cht trung
bnh.
nA =
322,56
22400
=0,0144mol; n
Br
2
=
3,84
160
=0,024 mol ; n
CO
2
=
1,6896
44
=0,0384 mol.
Gi cng thc phn t trung bnh ca X, Y : C
n
H
2n+2-2k

Theo bi ton ta c th tnh c s lin kt trong X, Y.
T cng thc ca bi m u (cc bn xem li bi s 1 nm vng hn) ta c :
k
=
n
E
2
n
A
=
0,024
0,0144
=
5
3

Vn dng tnh cht gi tr trung bnh : k1 =1 <k
<k2 =2
Mt khc t chy A : ta lun tnh c s CTB trong A thng qua cng thc :
S CTB =
n
CO
2
n
A
n =
0,0384
0,0144
=
8
3

Vn dng tnh cht gi tr trung bnh : n1 =2 <n <n2
Vy trong A th s c 1 cht l C2H4 (ng vi k1 =1).
Gi a, b ln lt l s mol ca X, Y a + b = 0,0144 mol (1)
Trng hp 1 : X l C2H4 v Y l hydrocarbon mch h c k : CnH2n +2-2k (hoc
ngc li, v vai tr X, Y l tng ng nhau).

62
p dng tnh cht gi tr trung bnh ta c : n =
8
3
=
2u+nb
u+b
2a + nb = 0,0384 (2)
k
=
a+kb
a+b
=
5
3
a + kb = 0,024 (3)
T (1), (2), (3) bin i bng cch rt ht a trong biu thc ta c mt biu thc
n gin :n =k+1 ch c cp nghim : n =3, k =2 l cp nghim ph hp _
X: C
2
H
4
Y: C
3
H
4

Trng hp 2 : X l C2H2 (k =2), vy Y s c k =1 v c CTPT : CmH2m
Lc ny ta s : k
=
2u+b
u+b
=
5
3
2a +b =0,024 (4)
T (1), (2), (4) : Gii ra ta c m =4 Y l C4H8 _
X: C
2
H
2
Y: C
4
H
8

Nhn xt : Bi ton ny tng i hay, hay l ch chng ta bit mt cht hoc X
hoc Y c n =2, v ta cng bit c k =1 trong hn hp A. Do vy cc bn s d b
tc gi dn dt n trng hp 1 v kt lun ngay nghim ny l cp nghim duy
nht. Cho nn bi ton ny vn dng ti a phng php trung bnh, cng nh cn
phi c mt s suy lun sc bn mi khng th b st nghim c.


63
BI 7 AREN CnH2n - 6 (n 6)
A. KIN THC C BN
I. GII THIU
Aren l tn gi mt nhm hp cht hydrocarbon c c cu sn carbon chnh
cha ti thiu l mt vng benzen. V d : Toluen, naptalen, antracenAren cn
c gi l hydrocarbon hng phng (t hng phng c s dng dch
thut ng aromatic (Anh), aromatique (Php), nhm mc ch trnh hiu lm nu
dch n gin l thm v ngay khi ngh aromatic, cc nh ha hc phng Ty
nhn mnh rng, trong lnh vc ha hc t ny khng c ngha l thm thng
thng. Do tnh hng phng l c tnh ca aren, ni ln bn c bit ca
nhm hp cht do c h thng in t tip cch trong phn t nn a n s
cng hng trn u, khc vi trng hp cng hng trong mch h, khng phi
tnh cht d chu c th ngi c (thm). (Theo GS.TSKH L Ngc Thch, Ha
Hc Hu C Cc Nhm nh Chc Chnh HKH T Nhin TP. H Ch Minh).
II. DANH PHP
1. Tn thng thng

Benzen Toluen Cumen
HC
CH
2

Styren o Xilen m Xilen

p Xilen biphenyl

64
2. Tn theo h thng
Benzen c chn lm tn tc, tn cc nhm th c t trc v vit
lin vi t benzen

Bromobenzen n propylbenzen nitro benzen
Nu c nhiu nhm th, th v tr ca nhng nhm th ny c s v tr theo
nguyn tc s nh nht v khi vit th tun theo th t mu t.
CH
3
Br
CH
3

4 bromo 1, 3 dimetylbenzen 2 metyl 1,4 dinitrobenzen
III. L TNH
Do tnh phn cc thp, nn hu ht cc aren thng c l tnh tng t nhau
nh cc hydrocarbon khc. t tan trong nc, tan tt trong cc dung mi hu
c khng phn cc. Hu ht chng nh hn nc, im si tng theo phn t
khi. im chy ty thuc vo hnh dng phn t, ng phn para c im
chy cao hn cc ng phn khc v t tan nht. V nu cng i xng th n
cng d kt thnh mng tinh th lm cho im chy cng cao v ha tan
cng thp.
Benzen l cht lng khng mu, c mi thm c trng, t
s
0
=80
0
C. Benzen nh
hn nc (d = 0,9g/mL), khng tan trong nc, tan tt trong dung mi hu
c nh ru, aceton, ete v bn thn benzen cng l dung mi tt ha
tan m, cao su, nha ng
IV. HA TNH
c im chung ca cc aren v tnh cht ha hc l : D th, kh cng bn
vng vi tc nhn oxi ha.

65
1. Phn ng th
a. Halogen ha
Benzen v cc ng ng khng phn ng vi dung dch brom nhng phn ng
d dng vi Brom dng nguyn cht khi c mt bt st lm cht xc tc.

+ Br2
Pc
=== + HBr

Toluen tham gia phn ng th vi Brom vng mt cch d dng hn v to
ra sn phm gm hai ng phn

+ HBr

o - Bromobenzen
+ Br2
Pc
====

+ HBr

p Bromobemzen
Quy lut th vng benzen : Khi vng benzen c cha sn cc nhm y
in t : Gc alkyl, - OH, - OCH3, - NH2, - N(CH3)2 th phn ng th d dng
hn benzen v u tin v tr th ortho v para. Ngc li khi vng benzen
c sn nhm th ht in t : -NO2, - CHO, - COOH,) th phn ng th xy ra
kh khn hn benzen v u tin xy ra v tr meta.

66
Lu : Di tc dng ca nh sng (khng c cha bt st) cc ng ng li tham
gia phn ng th v tr ca gc alkyl mt cch d dng hn hn metan.

+ Br2
uskt
===== + HBr

b. Phn ng nitro ha
Khi un nng nh benzen vi hn hp HNO3 m c v H2SO4 m c s xy ra
phn ng th to thnh nitrobenzen.

+ HNO3
H
2
SO
4
===== + H2O

Ring i vi Toluen phn ng nitro ha xy ra d dng hn, phn ng xy ra
nhit phng v to ra hn hp 3 ng phn : o, m, p nitrotoluen.

+ HNO3
H
2
SO
4
=====

NO
2

67
c. Phn ng sulfo ha
un nng benzen vi H2SO4 m c ng thi trng ct nc ra khi hn hp
phn ng s thu c acid benzensulfonic.

+ HOSO3H
170
0
C
==== + H2O

ng dng ca phn ng : Phn ng sulfo ha dodecylbenzen C6H5 C10H21 c
dng trong vic sn xut bt git tng hp.
d. Alkyl ha (Alkyl ha Friedel Crafts).
Phn ng ny c tm thy do hai nh ha hc Charles Friedek (Php) v Jame
Mason (M) bo co vo nm 1887 khi cho halogenuralkyl RX tc dng vi
benzen di s hin ca nhm clorur (AlCl3 khan) phn ng cho ra akylbenzen
tng ng. Phn ng ny rt hu dng v n cho php gn trc tip mt nhm
alkyl vo nhn benzen. Tuy nhin c mt s gii hn nh khng th thay RX bng
Ar X hoc vinyl halogenur. Nhng clorur benzyl th c th s dng c.

+ RX
AICI
3
==== + HCl

C th thay dn xut halogen bng ancol hoc alken alkyl ha benzen.

+ CH3 CH2 OH
H
2
SO
4
=====

+ CH2 =CH2
H
2
SO
4
=====


68
Nu alken l propen ta s thu c sn phm chnh Cumen :

+ CH2=CH CH3
H
2
SO
4
=====

Cumen
2. Phn ng cng
Phn ng cng vng thng xy ra kh khn hn so vi cc hydrocarbon khng
no.
a. Phn ng cng Hydrogen

+ H2
xt
====
Benzen cyclohexan
b. Phn ng cng clor

+ 3Cl2
askt
===

1,2,3,4,5,6 hexaclorocyclohexan
(Thuc su 6,6,6)
3. Phn ng oxi ha
a. Oxi ha hon ton (phn ng chy)
Benzen v cc ng ng ca benzen chy trong oxy cho ngn la mu sng,
v sinh ra nhiu mui than, v hm lng Carbon nhiu.
CnH2n 6 +
3n-3
2
O2 nCO2 + (n-3)H2O


69
Nhn xt : Phn ng t chy sinh ra n
H
2
O
<n
CO
2

nA =
n
CO
2
-n
H
2
O
3

b. Phn ng oxi ha khng hon ton
Benzen khng tham gia phn ng vi cc tc nhn oxi ha mnh, nhng
Toluen v dy ng ng tc dng c vi KMnO4, K2Cr2O7 un nng s b
oxi ha cc mch nhnh to ra mui v acid hu c.
V d :

+ KMnO4
t
c

=== +2MnO2 + KOH + H2O

Acid benzoic
H qu : Phn ng ny nhn bit Benzen v Toluen.
Lu : Nu nhm alkyl trn vng benzen di hn nhm CH3 th phn ng
oxi ha mch nhnh vn u tin xy ra v tr i vi vng .
V d :
C6H5CH2CH2CH3 + KMnO4 C6H5COOH
V. IU CH
1. i t ngun chng ct du m
Cc Aren c iu ch bi qu trnh chng ct nha than v qu trnh
Reforming du m thu c mt lng ln benzen, toluen v naphtalen.
2. ehydro ha vng n hexan v n heptan thu c benzen v toluen :
CH3(CH2)4CH3
AI
2
0
3
/ C
2
0
3,
500
0
C
============== C6H6 +4H2
CH3(CH2)5CH3
Xt,p,t
c
===== C6H5CH3 +4H2
3. Dehydro ha cyclohexan
C6H12
Xt,t
0
=== C6H6 +3H2
4. Trng hp acetylen
3C2H2
C,600
0
===== C6H6
5. Alkyl ha benzen iu ch cc dy ng ng
C6H6 +CnH2n+1Cl
AICI
3
==== C6H5CnH2n+1 +HCl

70
VI. VN M RNG
THPT phn ng th nhn benzen tng i n gin, y xin m rng vn
th nhn benzen (ch yu cho cc bn c tham kho thm). Vn ny c trch
t cun sch : Ha Hc Hu C Cc Nhm nh Chc ca thy : GS. TSKH L Ngc
Thch B Mn Ha Hu C i Hc Khoa Hc T Nhin TP. H Ch Minh (ni tc
gi ang theo hc).
1. phn ng
Ch c mt mt sn phm c to ra khi tc nhn thn in t tc kch vo
benzen. Nhng nu trn nhn hng phng c trc mt nhm th, th
nhm th ny nh hng trn phn ng ca cht nn v nh hng v tr gn
vo ca tc nhn thn in t.
2. phn ng
Mt s nhm th lm tng hot phn ng lm cho cht nn phn ng hn so vi
benzen. Ngc li, mt s nhm th gim hot cht nn lm cho n phn ng
km hn benzen.
V d : Cng nh s nitro ha, nhng mi cht nn sau y c mt phn ng
khc nhau.

100 1 0,033 6. 10
-6

Vn tc nitro ha tng i
3. S nh hng
Bn cht nhm th - Y sn c trn nhn benzen quyt nh v tr gn vo nhm
th th hai. Ba sn phm th orto - , meta -, para -, khng to thnh cng s
lng.
V d : S nitro ha trn mt s cht nn khc nhau

+ HNO3
H
2
S0
4
====

NO
2

71

Y orto meta para
Gim hot nh hng meta
-N
+
(CH3)3 2 87 11
-NO2 7 91 2
-COOH 22 76 2
-CN 17 81 2
-COOC2H5 28 66 6
-COCH3 26 72 2
-CHO 19 72 9
-SO3H 21 72 7
Gim hot nh hng orto, para
-F 13 1 86
-Cl 35 1 64
-Br 43 1 56
-I 45 1 54
Tng hot nh hng orto, para
CH3 63 3 34
-OH 50 0 50
-NHCOCH3 19 2 79
Bng so snh s nh hng phn ng nitro ha trn C6H5Y
Tng qut cc nhm th trn nhn hng phng c th chia thnh ba loi : Tng
hot nh hng orto, para, Gim hot nh hng orto, para, Gim hot nh
hng meta.
phn ng v s nh hng trong phn ng th thn in t hng phng
chu s nh hng bi tc ng ca hiu ng cm v hiu ng cng hng.
Nhng nhm th -OH, -OCH3, -NH2 l nhng nhm tng hot v hiu ng tng
cng l y in t vo nhn benzen (hiu ng cng hng mnh hn hiu ng
cm).
Nhng nhm th -CN, -CO, -COO, -NO2 l nhng nhm th gim hot bi v c hai
loi hiu ng cng hng v hiu ng cm u rt in t.
Cn nhm th gim hot v hiu ng tng cng l rt in t (hiu ng cm mnh
hn hiu ng cng hng).
Nhng nhm th Alkyl cho hiu ng cng hng dng nn tng hot phn ng
v cho s nh hng orto v para.


72
B. PHNG PHP GII TON
VN 1 : PHN NG NITRO HA BENZEN
PHNG PHP
Phn ng nitro ha benzen theo l thuyt th benzen phn ng vi HNO3 vi
s hin din ca H2SO4 c nng. Ty vo thi gian m chng s th vo vng
benzen mt, hai hay ba nhm NO2.
Lc ta biu din phng trnh di dng tng qut :
C6H6 + xHO NO2
H
2
SO
4
===== C6H6 x(NO2)x +xH2O
iu kin ca x thng l : 1 x 3.
VN 2 : NHN BIT V TCH BENZEN V ALKYL BENZEN
PHNG PHP
Nhn bit :
Benzen : khng tan trong nc, khng lm mt mu dung dch nc brom,
khng b cc tc nhn oxi ha mnh nh : KMnO4, K2Cr2O7.
Thuc th nhn bit : Dng hn hp HNO3/ H2SO4
Hin tng : Cht lng nitrobenzen c mi hnh nhn.
ng ng benzen : khng tan trong nc, khng lm mt mu dung dch
nc brom.
Thuc th nhn bit : dung dch KMnO4 un nng.
Hin tng : mu ca dung dch nht t t.
Tch
Benzen v cc alkylbenzen khng tan trong nc nn dng phng php lc
tch.
C. BI TP
Bi 1 Hn hp X gm hai hydrocarbon A, B c khi lng a gam. Nu em t chy
hon ton X th thu c
132a
41
gam CO2 v
45a
41
gam H2O. Nu thm vo X mt na
lng A c trong X ri t chy hon ton thu c
165a
41
gam CO2 v
60,75a
41
gam H2O.
Tm CTPT ca A,B bit X khng lm mt mu dung dch brom v A, B thuc
hydrocarbon hc.
Gii

73
Phn tch : y ta c n s a th cch tt nht ta nn dng phng php t chn
lng cht tnh ton cho d dng. i vi nhng bi ton c cha n th ta nn
dng phng php t chn lng cht gii quyt bi ton cho d dng.
Ta chn a =41 m
CO
2
=132 gam n
CO
2
=3 mol ; m
CO
2
=165 gam n
CO
2
=3,75 mol
m
H
2
O
=45 gam n
H
2
O
=2,5 mol ; m
H
2
O
=60,75 gam n
H
2
O
=3,375 mol
S mol CO2 v H2O c trong
1
2
A l :
n
CO
2
=3,75 3 =0,75 mol ; n
H
2
O
=3,375 2,5 =0,875mol
S C
A
SH
A
=
n
CO
2
2n
H
2
O
=
3
7

CTG ca A l : (C3H7)n 7n 3n.2 +2 n 2 A: C6H14 l duy nht.
S mol CO2, H2O sinh ra t B : n
CO
2
=3 2*0,75 =1,5; n
H
2
O
=2,5 0,875*2 =0,75
S C
A
SH
A
=
n
CO
2
2n
H
2
O
=
1,5
0,752
=1 CTG ca B l : (CH)n n = 6 l cng thc tha mn.
Vy A l : C6H14 v B l : C6H6.
Bi 2 Cho 0,5 kg benzen tc dng vi hn hp gm 0,9 kg H2SO4 96% v 0,72 kg
HNO3 66%. Gi s benzen c chuyn ht thnh nitro benzen v nitrobenzen c
tch ht ra khi hn hp acid d. Tnh khi lng nitrobenzen thu c v khi
lng ca cc acid d. (Bit phn ng xy ra c hiu sut t 100%).
Gii
Phn tch : y l dng ton thun ty ca phn ng nitro ha benzen, gii quyt
dng ton ny ta dng phng php 3 dng gii quyt. (Lu l i vi dng bi
ton ny th ta vit tt c cc tc cht v dng cng thc tng qut, thun tin cho
vic tnh ton).
Phng trnh phn ng : C6H6 + HNO3
H
2
S0
4
==== C6H5NO2 +H2O
M =78 M =63 M =123
Ban u : 0,5 kg 0,72kg 0 kg
Phn ng : x x x
Sau phn ng : 0,5 x 0,72 x x

74
Khi lng nitrobenzen thu c l : m =
1230,5
63
=0,7885 gam
Khi lng HNO3 nguyn cht ban u l : m =
0,7266
100
=0,4752 kg
Khi lng H2SO4 nguyn cht l : m =
0,996
100
=0,864 kg
Khi lng HNO3 tham gia phn ng vi Benzen : mp =
0,578
63
=0,4038 kg
Khi lng HNO3 nguyn cht cn d : 0,4752 0,4038 =0,0714 kg
Bi 3 Nitro ha benzen bng mt hn hp dung dch HNO3/ H2SO4 thu c hai cht
hu c A, B. t chy hon ton 7,275 gam hn hp A, B thu c CO2, H2O v 0,84
lt kh N2 (ktc). Tm cng thc cu to ca A, B v tnh phn trm khi lng ca A,
B trong hn hp.
Gii
Phn tch : y khng ni r l nitro ha theo t l bao nhiu, nn ta vit phng
trnh di dng tng qut.
C6H6 + xHO NO2
H
2
SO
4
===== C6H6 x(NO2)x +xH2O
(A, B)
t chy 7,275g thu c n
N
2
=
0,84
22,4
=0,0375 mol A p dng bo ton nguyn t N2
trong A, B ta c : xa =0,0375*2 =0,075 mol
78+45x
x
=
7,275
0,075
=97x =1,5
T tnh cht gi tr trung bnh suy ra : Chc chn trong hn hp A, hoc B s cha 1
nhm nitro (-NO2) v cn li cht kia s cha nhiu hn 1 nhm th nitro.
Gi s nh A l : C6H5NO2 vi s mol l a B l : C6H4(NO2)2 vi s mol l b
Vn dng tnh cht gi tr trung bnh ta c : a =b =0,025 mol
%mA =
1230,025
7,275
*100% =42, 27% %mB =(100 42,27)% =57,73%

CTCT ca A, B :

75
Bi 4 Mt cht hu c A c CTPT l C8H8 tc dng c vi dung dch brom theo t
l 1 :1, nhng tc dng vi H2 theo t l 1 :4. Tm cng thc cu to ca A
Gii
Phn tch : y l dng ton cho bit CTPT bt chng ta i tm CTCT, gii quyt
nhng bi ton dng ny, bc u tin chng ta phi tnh c bt bo ha
xem xt trong CTCT ca cht c dng vng, h hay kt hp c hai. Bc tip theo
chng ta da vo d kin bi ton ri d ton v vit CTCT ca chng.
bt bo ha : a =
82-8+2
2
=5
Nh vy t nhng phn tch trn ta c : A tc dng vi dung dch brom theo t l
1 :1 Trong A cha nhm CH=CH2 bt bo ha cn li l 4
Mt khc A tc dng vi H2 theo t l 1 :4 A co 4 lin kt Trong A c cha 3
lin kt v mt vng
CTCT ca A l :

Styren (vinylbenzen)
Bi 5 Hydrocarbon A c CTPT l C8H10 khng lm mt mu nc brom khi b hydro
ha chuyn thnh 1,4 dimetylcyclohexan. Xc nh CTCT ca A gi tn chng.
Gii
bt bo ha cha trong A : a =
82-10+2
2
=4
Theo d kin bi ton khi b hydro ha A chuyn thnh 1,4 dimetylcyclohexan
A co cha vng, v c cha hai nhm th metyl ( - CH3) A co 1 vng v 3 lin kt
. Mt khc A khng tham gia phn ng vi dung dch brom 3 lin kt ny nm
trong vng A co CTCT :

1,4 dimetylbenzen
HC
CH
2

76
Bi 6 Cho 13,8 gam alkylbenzen A tc dng vi dung dch brom c bt Fe xc tc thu
c hai dn xut monobrom c khi lng 20,5 gam. Trong mi dn xut u c
46.784% brom trong phn t. Tm cng thc phn t ca A v hiu sut phn ng.
Gii
Phn tch : bi cho bit hai d kin quan trng : th nht l A tc dng vi
brom theo t l 1 :1 (mono). Th hai l cho bit t l phn trm ca brom. m bi
ton ny ta da vo d kin bi ton theo t l phn trm ca Brom. Nhng im
mu cht quan trng y l lm sao gi mt CTPT ca A sao cho ph hp.
Gi CTPT ca mi ng phn l C6H4-CnH2n+1Br. Theo bi ra ta c :
46,784 =
80
157+14n
*100 n = 1 CTPT ca mi ng phn l : C7H7Br CTCT ca A

o- bromobenzen
+Br
Pc
====

p bromobenzen
nA =
13,8
92
=0,15 mol =nsp theo p msp theo p =0,15*171 =25,65 gam
Hiu sut phn ng l : H=
20.5
25,65
*100% =79,92%
Bi 7 Hydrocarbon A l cht lng, t khi hi so vi khng kh l 2,7. t chy hon
ton A thu c CO2 v H2O c t l khi lng
m
CO
2
m
H
2
O
=
4,9
1
. Bit rng khi cho A tc
dng vi brom khan t l 1 :1 c mt bt Fe xc tc thu c cht B v kh D. Kh D

77
hp th hon ton bi 2 lt dung dch NaOH 0,5M. trung ha NaOH d cn 0,5 lt
dung dch HCl 1M. Xc nh A.
Gii
Phn tch : c k bi ton ta c th d on c bi ton ny lin quan n nhm
hydrocarbon thm. (C mt xc tc Fe khi cho A tc dng vi Brom). Nu chng ta b
cun theo nhng d kin ca tc gi th chng ta s mt thi gian. y ch cn
d kin t l khi lng ca kh CO2 v H2O c th suy ra c p n bi ton.
Ta c MA =2,7*29 =78 g/ mol C6H6 (d on trong u).
Mt khc
m
CO
2
m
H
2
O
=
4,9
1

44n
CO
2
18n
H
2
O
=
4,9
1

n
CO
2
2n
H
2
O
=
S C
A
S H
A
=1 CTG : (C6H6)n n =1
Vy cng thc A l C6H6.
Bi 8 Hydrocarbon A c cha vng benzen khng c kh nng lm mt mu dung
dch brom. %C chim 90%. A tc dng vi brom theo t l 1 :1 cho 1 sn phm duy
nht. Tm cng thc phn t ca A v vit cng thc cu to ca A.
Gii
Phn tch : y bi ton ni kh r l A cha vng benzen, A tc dng vi Br2 theo
t l 1 :1 sinh ra mt sn phm duy nht A co tnh i xng cao. M c mu cht
bi ny kh d dng nh t l %C ta c th tm c CTPT.
Gi CTPT ca A l CxHy %C = 99% %H = 10%
12x
=
90
10

x
=
9
12

CTG A : (C9H12)n n = 1 (ph hp vi dy ng ng benzen) CTPT A : C9H12
V A tc dng vi Br ch sinh ra 1 sn phm duy nht A co tnh i xng cao.

1,3,5 trimetylbenzen

78
Bi 8 NGUN HYDROCARBON THIN NHIN
A. KIN THC C BN
I. DU M
1. L tnh
Du m l mt hn hp lng, snh, c mu nu en, c mi c trng, nh hn
nc v khng tan trong nc. Du m c xem l sn phm phn hy rt
chm ca nhiu xc ng thc vt vi su di t nh tc dng ca cc vi
khun ym kh. Du m c khai thc t cc m du di lng t (trong lc
a cng nh thm lc a). Du m nm trong ti du gm 3 lp : Lp trn
cng l lp kh c p sut cao gi l kh ng hnh, lp gia l du lng, lp
cui l lp nc mn.
2. Thnh phn du m
L mt hn hp vi hng trm cc cht hydrocarbon khc nhau v cc cht hu
c c cha cc nguyn t Oxy, lu hunh, nit. Hm lng Carbon khong %C =
82 87% ; H% =11 14% cn li l %O, %S, %N Khng c du no ging du
no. Vit Nam du ca chng ta thuc loi du sch (hm lng S rt t). Lu
hunh l cht gy ng c xc tc v lm hao mn thit b (H2S l nguyn nhn
chnh).
3. Chng ct du m
Phn on Nhit si
0
C
S Carbon
trong phn
t
ng dng
1. Kh <40 C1 C4 Nhin liu, nguyn
liu dng tng hp
hu c.
2. Ete du ha 40 70 C5 C6 Dung mi
3. Xng nh 40 - 200 C5 C11 Nhin liu, dung
mi hu c
4. Xng thng 120 - 240 C8 C11 Nhin liu dung
mi hu c.
5. Du ha 150 - 310 C12 C18 Nhin liu t.
6. Du diezen 250 - 350 C13 C30 Nhin liu.

Bng chng ct phn on theo nhit ca du m


79
Phn cn li sau khi chng ct mazut, em i chng ct phn on Mazut
c :
- Du nhn bi trn my.
- Vasolin hn hp hydrocarbon lng v rn dng trong y hc.
- Parafin hn hp cc hydrocarbon rn , dng lm nn v cht cch in.
- Hc n dng lm nha ng.
Ch s Octan (ch s kch n): dng nh gi cht lng xng, ch s cng
cao th xng cng tt. Theo quy c xng c ch s octan 100 l xng ch cha
iso- octan.

2,2,4 trimetylpentan
- Xng c ch s octan bng 0 l n heptan.
4. Ch bin du m bng phng php ha hc
a. Crackinh
- Crackinh bng nhit nhng phn on nng ca du m (du diezen, du
mazut) nh thu c kh v xng c phn t lng nh hn.
b. Reforming :
- L qu trnh dng nhit v xc tc nhm bin i cc hydrocrbon khng
nhnh thnh c nhnh, t khng vng thnh c vng.
II. KH DU M V KH THIN NHIN.
1. Kh ng hnh
- C trong ti du, tan mt phn trong du m, mt phn lp trn to kh.
- Thnh phn ha hc cha : 24% metan, 20% etan, 17% propan, 8% butan,
2% pentan, phn cn li l cc cht khc : CO2, N2
2. Kh thin nhin
- Thng gp vng c du m, hoc khu vc ring b nn di p sut ln.
- Thnh phn ha hc : 95% metan, 0,6% etan, 0,3% propan, 0,1% cc ng
ng khc, cn li khong 4% H2S, N2


80
III. THAN M
- Than m c than gy, than bo, than bn Ch c than bo (than m) c
dng iu ch than cc v cung cp mt lng nh hydrocarbon.
1. Chng ct than bo trong l cc (1000
0
C) lm lnh
- Kh l cc : 65% H2, 25% CH4, cn li l CO2, N2
- Lp nc +NH3 : lm phn.
- Lp nha than : cht lng nht mu sm.
- Than cc thu c dng luyn kim.
2. Chng ct nha than
- Thu c nhiu loi hydrocarbon thm : benzen, toluen, xilen Cn cn li l
cht rn mu en dng lm nha ng.


81
BI 9 ALCOL (R(OH)n n 1)
A. KIN THC C BN
I. RU NO N CHC
Ru no n chc c cng thc phn t tng qut : CnH2n+1OH, ROH (n1)
1. Tnh cht vt l
- Tt c cc ru n chc, a chc u nh hn nc (d <1)
- Phn t alcol gm c hai phn : Phn R (cc gc hydrcarbon) khng tan c
trong nc, tan trong cc dung mi khng phn cc. Phn OH tan c
trong cc dung mi phn cc (v d : nc, acid). Do s ha tan ca cc
alcol cn ph thuc rt nhiu vo thnh phn ca R- v OH.
+ Nhng alcol tan v hn trong nc thng l nhng alcol c gc
hydrocarbon mch ngn (C1 C3). Ngc li nhng alcol c mch
hydrocarbon di th s tan trong nc c phn kh khn.
+Alcol ha tan c trong nc nh c s lin kt hydrogen lin phn t ca
nhm hydroxyl ( - OH) vi nc.

- Tng t nh cc hp cht khc im si ca alcol tng theo khi lng phn
t. im si ca alcol cao hn alkan, cycloalkan tng ng v alcol to c
lin kt hydrogen lin phn t.
2. Bc ru danh php.
a. Bc ru
- Bc ca ru l bc ca Carbon m nhm OH gn trc tip ln n Ru
c bc ti a l 3.
R- CH2 OH
Ru bc 1

Ru bc 2 Ru bc 3
b. Danh php
- Danh php thng thng : Ru + Tn alkyl + ic
V d : C2H5 OH : Ru metylic ; C3H7 OH : Ru propylic


82
- Danh php IUPAC :
+Chn mch chnh c dy carbon di nht c cha nhm hydroxyl (- OH), tn
tc ca alcol ly theo tn ca hydrcocarbon tng ng vi dy chnh (Alkan,
alken, cycloalkan). Thm tip v ng - ol vo sau tn tc.
+ nh s cc carbon trn mch chnh sao cho carbon mang nhm hydroxyl
mang ch s nh nht.
+ nh s cc nhm th (nu c) cng theo quy tc trn v vit theo k t A,
B, C
1 2 5
3 4

2 metylpentan 2 ol
3. Mt s ru khng bn
a. Ru c nhm OH gn vo carbon c cha ni i
- Ru ny khng bn trong mi trng trung tnh hoc acid, lp tc chuyn v
aldehyd hoc ceton.
V d
CH3CHO

- Ru khng no ch tn ti khi nhm OH gn vo nguyn t Carbon mang ni
n Trong pha n t ru c s C 3. (tr trng hp nhn thm).
V d
CH2 =CH CH2 OH
Ru allylic
Propenol
Phenol
b. Ru cha nhiu nhm OH gn trn cng mt nguyn t C
- Ru ny s khng bn v cc nhm OH s tng tc qua li vi nhau
Chng s hydrat ha ln nhau to ra aldehyd, ceton hoc acid.

R CHO

Nhn xt : S nguyn t Oru S nguyn t Cno

83
4. Tnh cht ha hc
Trong nhm chc hydroxy OH, nguyn t oxy c m in ln nn ht e
mnh Hai lin kt C O v O H mt phn no b phn cc v pha oxy
d b t trong qu trnh tham gia phn ng ha hc.
_
(1)Tc dng vi kim loi kim kh H
2

(2)Tc dng vi acid c oxy este
(3)Oxy ha khng hon ton aldehyd,ceton

R O H

_
(1)T 1 phn t iu alken
(2)T 2 phn t iu ete
(3)Tc dng vi acid khng c oxy este

Nu gc R y electron cng mnh thi lin kt C O cng phn cc d b ct
t D dng tch nc (phn ng este ha i vi acid v c, phn ng
tch nc alken) lin kt O H cng km phn cc kho b ct t
phn ng este ha vi acid hu c (phn ng este), phn ng vi kim loi
kim c phn hn ch.
a. Tc dng vi kim loi kim
ROH + Na RONa +
1
2
H2
Nhn xt : nru =nNa =2n
H
2

Natri alcolat R ONa l mt cht rn b thy phn hon ton
RONa + H2O ROH + NaOH
H qu : Phn ng ny c dng ti to ru.
b. Phn ng este ha
Cc phn ng este ha thng l thun nghch, khng hon ton . Mun phn
ng xy ra vi hiu sut cao, ngi ta dng H2SO4 c xc tc v ht nc lm
chuyn dch cn bng v pha thun.
ROH +RCOOH RCOOR +H2O

H
2
SO
4

84
Ru c bc khc nhau th kh nng tham gia este ha cng khc nhau.
Ru bc I > Ru bc II > Ru bc III

c. Phn ng dehydrat ha (loi H2O)
Dehydrat ha t mt phn t ru Alken, phn ng tun theo quy tc
Zaixep. Phn ng c thc hin nhit trn 170
0
C vi xc tc l H2SO4
- Quy tc Zaixep :Phn ng tch nc tun theo quy tc nhm OH s b tch
nguyn t bc cao hn
V d :

But 2 en (sp chnh)

H
2
SD
4,
17
C
=========

But 1 en (sp ph)
Dehydrat ha t hai phn t ru ete
- Phn ng dehydrat ha t hai phn t ru sinh ra ete nhit di 170
0
C
ROH + ROH
140
0
C
==== R O R +H2O
2ROH
140
0
C
====R O R +H2O
Nhn xt : Nu c x ru khc nhau s to ra s ete ti a l :
S ete ti a =
x(x+1)
2

Trong s ete s c x ete i xng
n
H
2
D
= n
ete

1
2
n
alul

p dng nh lut bo ton khi lng :

malcol p = mete + mnc


85
Phn ng dehydrat ha v dehydro ha ng thi Alkadien
C2H5OH
AI
2
0
3
,450
0
C
========= CH2 =CH CH =CH2 +H2 + H2O
Buta 1, 3 dien
d. Phn ng oxi ha khng hon ton
Ru bc I
[O]
== Aldehyd
[O]
== Acid
V d : RCH2OH
+ O
2
,Cu/ t
0
========RCHO
+O
2,
Mn
2+
=======RCOOH
Ru bc II
[O]
== Ceton
V d :
+0
2
,Cu/ t
0
======= + H2O

Ru bc III khng b oxy ha bi cc tc nhn oxy ha mnh trong mi
trng trung tnh, mi trng kim. Chng ch b oxy ha trong mi trng
acid sinh ra mt hn hp sn phm gm acid v ceton.
Oxy ha ru bng xc tc men
C2H5OH +O2
mcn gIm
======= CH3COOH +H2O
Nhn xt : Da vo sn phm ca s oxy ha ru ta c th phn bit c bc ca
ru tham gia phn ng.
e. Phn ng oxy ha hon ton (phn ng chy).
Ru no chy sn phm sinh ra gm nc v kh CO2
CnH2n+1OH + O2 nCO2 +(n+1)H2O
Nhn xt :
- Khi t chy ru no lun c : n
CD
2
< n
H
2
D

nru = n
H
2
D
- n
CD
2

f. Phn ng vi trihalogenur phosphor (PX3)
Alcol tc dng vi trihalogenur phosphor sn phm thu c l halogenur
alkyl tng ng
3ROH + PX3 3RX + H3PO3
V d : C2H5OH +PBr3 C2H5Br +H3PO3

86
C
O
g. Tng hp Williamson
u tin chuyn ha alcol thnh alkoxid, sau cho alkoxid tc dng vi
halogenur alkyl. Phng php ny tng qut hn, c th iu ch c eter i
xng v bt i xng vi hiu sut cao.
ROH
+ Nu
=== RONa
R
|
X
==ROR
h. ru
ru l s mL ru etylic c trong 100mL hn hp ru vi nc
ru =
v
r
v
dd
*100
5. iu ch
a. T Alken
Alcol c th c iu ch bng s thy ha alken. Bi v s thy ha trc
tip alken vi dung dch acid t dng trong phng th nghim cho nn hai
phng php gin tip sau y thng dng hn :
Hydrobor ha oxid ha Cho sn phm cng syn, s thy ha tun theo
quy tc phn Markovnikov (do c hiu ng lp th nn Bor s tc kch vo
Carbon c t hydrogen hn)
V d :
CH3CH=CH2
1.BH
3
,1HP
2.0H
-
,H
2
0
2

========= CH3 CH2 CH2 OH
b. T halogenur alkyl
RX +OH
-
ROH
- Phn ng xy ra tt trong trng hp halogenur alkyl nht cp v nh cp.
Cn halogenur tam cp thng cho sn phm ph l alken, sn phm ny tr
nn quan trng trong iu kin s dng baz mnh v un nng.
V d :
C2H5Cl +KOH C2H5OH +KCl
c. Hon nguyn ha hc nhm carbonyl

Mt trong nhng phng php tng qut nht iu ch alcol l hon
nguyn hp cht carbonyl.
- Hon nguyn [H] (k hiu quc t ch s hon nguyn) theo ngha hu
c l phn ng thm hydrogen vo phn t bt bo ha, ngc li vi phn
ng oxid ha.
- Aldehyd hon nguyn Alcol bc nht


87
[H]
========

Aldehyd alcol bc nht
V d : CH3CH2CHO
[H]
===== CH3CH2CH2 OH
HCHO
[H]
=======CH3 OH
- Ceton hon nguyn Alcol bc hai

[H]
========

V d :

[H]
=====

Aceton propan 2 ol
C nhiu tc cht dng hon nguyn nhm carbonyl thnh alcol thnh alcol
tng ng, nhng ch yu ngi ta dng NaBH4, v LiAlH4.
- T acid v ester ru bc nht.
[H]
====

V d : CH3COOH
[H]
===== CH3CH2 OH

[H]
=====

V d : CH3COOC2H5
[H]
===

d. Mt s trng hp c bit iu ch ru
iu ch ru metylic

88
H
2
C CH
2
OH OH
CO +2H2
ZnO,200
0
C,500atm
============== CH3 OH
iu ch ru etylic : thy phn tinh bt v cenluloz
(C6H10O5)n +nH2O
mantaz
===== nC6H12O6
C6H12O6
mcn ru,32
0
C
=========== CO2 + C2H5OH
II. RU A CHC R(OH)n (n 2)
Ru a chc l hp cht hu c c cha nhiu nhm OH lin kt vi nhng
nguyn t carbon khc nhau.
- Hai cht quan trng :

Etylen Glicol Glycerin
- Glycerin l cht lng mu snh c dng xir, khng mu tan v hn trong
nc c v ngt, ht m t
s
0
=290
0
C (dng trong cng nghip da, mc in, kem
nh rng).
- Etylen Glicol l cht lng dng xir, khng mu, khng mi v ngt, c.

1. Tnh cht ha hc
a. Tc dng vi kim loi kim
R(OH)n + nNa R(ONa)n +
n
2
H2
Nhn xt : Phn ng gia ru a chc v kim loi kim lun c :
n
H
2
nru =
2
n
n
H
2

b. Phn ng este ha

89
Phng trnh phn ng tng qut ru a chc vi acid c dng nh
sau :
mR(OH)n + nR(COOH)m Rm - (COO)m.n Rn + m.nH2O

c. Phn ng vi Cu(OH)2

+OH Cu OH +

ng (II) Glycerat
(phc mu xanh thm)
Nhn xt : Phn ng gia ru a chc v ng (II)
hydroxid l mt phn ng c trng ca ru a chc.
N dng phn bit gia ru a chc vi ru n
chc. Phn ng cho kt ta dng phc mu xanh
thm nh hnh bn.

d. Phn ng dehydrat ha
H
2
C
H
C CH
2
OH OH OH
KHSO
4
-2H
2
O
H
2
C C CH
OH
H
2
C C
H
CHO

H
2
C CH
2
OH OH
KHSO
4
-H
2
O
H
2
C
CH
OH
H
3
C CHO

e. Phn ng oxy ha
Ty theo iu kin oxy ha (cht oxy ha) ta c th thu c cc sn phm l
aldehyde, acid hoc kh CO2.
Glycerin c th b oxy ha thnh cc cht sau:


90
Glyceraldehyd HOOC CH2 COOH
Acid propanoic

Acid Glycerid
2. iu ch ru a chc
a. iu ch Etylen Glycol
+ i t phn ng oxy ha etylen
3C2H4 +2KMnO4 + 4H2O 3C2H4(OH)2 +2MnO2 +2KOH
+ i t phn ng cng halogen ca etylen
CH2 =CH2 + Cl2 Cl CH2 CH2 Cl C2H4 (OH)2
+ i t oxid etylen

+ H2O HO CH2 CH2 OH
b. iu ch Glycerin
+X phng ha cht cht bo

+ i t propen
Phn ng th halogen vo propen (Phn ng th alken thng xy ra
nhit cao). Sn phm thu c tu phn ng th l allylclorua, cht
ny tin hnh phn ng haloform to ra 1,3 iclo propan 2 ol t
cht ny cho tc dng vi NaOH ta s c Glycerin.
CH2 =CH CH3 +Cl2
500
0
C
Cl CH =CH CH3 +HCl

+Cl
2
+H
2
O

H
2
C
H
C CHO
OH OH

91

+Ln men Glucozo c mt NaHSO3
C6H12O6
NaHSO
3
+CH3 CHO +CO2

III. VN CN BIT
1. Ru etylic
tanol, cn c bit n nh l ru tylic, ancol etylic, ru ng
cc hay cn, l mt hp cht hu c, nm trong dy ng ng ca ru metylic,
d chy, khng mu, l mt trong cc ru thng thng c trong thnh phn
ca ung cha cn. Trong cch ni dn d, thng thng n c nhc n
mt cch n gin l ru. tanol l mt ancol mch thng, cng thc ha
hc ca n l C2H6O hay C2H5OH. Mt cng thc thay th khc l CH3-CH2-OH th
hin carbon nhm metyl (CH3) lin kt vi carbon nhm metylen (CH2),
nhm ny li lin kt vi oxy ca nhm hydroxyl (OH). N l ng phan ho hc
ca imetyl te. Ethanol thng c vit tt l EtOH, s dng cch k hiu ho
hc thng dng i din cho nhm tyl (C2H5) l Et. tanol c con ngi
s dng t thi tin s nh l mt thnh phn gy cm gic say trong ung
cha cn. Cc cn b kh trong cc bnh gm 9000 nm tui tm thy min
bc Trung Quc gin tip cho thy vic s dng cc ung cha cn trong s
nhng ngi sng thi k mi. Vic chit n ra di dng tng i
nguyn cht c thc hin ln u tin bi cc nh gi kim thut Hi gio v
h l nhng ngi pht trin ra ngh thut chng ctru trong thi k ca
ch khalip (vua cha Hi gio) thi k Abbasid (ting Rp: al-
Abbsidn). Cc ghi chp ca Jabir Ibn Hayyan (Geber) (721-815) cp ti
hi d chy ca ru c un si. Al-Kind (801-873) cng miu t r rng
qu trnh chng ct ru. Vic chng ct tanol ra khi nc c th to ra cc
sn phm cha ti 96% tanol. tanol nguyn cht ln u tin thu c vo
nm 1796 bi Johann Tobias Lowitz, bng cch lc tanol chng ct quathan ci.
Antoine Lavoisier m t tanol nh l mt hp cht ca cacbon, hir v
xy, v nm 1808, Nicolas-Thodore de Saussure xc nh c cng thc ha
hc ca n. Nm 1858, Archibald Scott Couper cng b cng thc cu trc ca
tanol: iu ny lm cho tanol tr thnh mt trong cc hp cht ha hc u
tin c s xc nh cu trc ha hc.

92
tanol ln u tin c tng hp nhn to vo nm 1826, thng qua cc c
gng c lp ca Henry Hennel Anh v S.G. Srullas Php. Michael Faraday
iu ch tanol bng phn ng hyrat ha tylen vi xc tc axt nm 1828, theo
mt cng ngh tng t nh cng ngh tng hp tanol cng nghip ngy nay.
tanol c sn xut bng c cng nghip ha du, thng qua cng ngh
hyrat ha tylen, v theo phng php sinh hc, bng cch ln men ng hay
ng cc vi men ru.
Hyrat ha tylen
tanol c s dng nh l nguyn liu cng nghip v thng thng n
c sn xut t cc nguyn liu du m, ch yu l thng qua phng php
hyrat ha tylen bng xc tc axt, c trnh by theo phn ng ha hc sau.
Cho etilen hp nc 300 C, p sut 70-80 atm vi cht xc tc l acid
wolframic hoc acid phosphoric:
H2C=CH2 +H2O CH3CH2OH
Cht xc tc thng thng l axt phtphoric, c ht bm trong cc cht c
xp cao chng hn nh iatomit (t cha to ct) hay than ci; cht xc tc
ny ln u tin c cng ty du m Shell s dng sn xut tanol mc
cng nghip nm 1947. Cc cht xc tc rn, ch yu l cc loi xt kim loi
khc nhau, cng c cp ti trong cc sch v ha hc.
Trong cng ngh c, ln u tin c tin hnh mc cng nghip vo
nm 1930 bi Union Carbide, nhng ngy nay gn nh b loi b th tylen u
tin c hyrat ha gin tip bng phn ng ca n vi axt sulfuric m c
to ra tyl sulfat, sau cht ny c thy phn to thnh tanol v ti to
axt sulfuric:
H2C=CH2 +H2SO4 CH3CH2OSO3H
CH3CH2OSO3H +H2O CH3CH2OH +H2SO4
tanol s dng cng nghip thng thng l khng ph hp vi mc ch
lm ung cho con ngi ("bin tnh") do n c cha mt lng nh cc cht c
th l c hi (chng hn mtanol) hay kh chu (chng hn denatonium-
C21H29N2OC7H5O2-l mt cht rt ng, gy t). tanol bin tnh c s UN l UN
1987 v tanol bin tnh c hi c s l UN 1986.

93
Ln men
tanol s dng trong ung cha cn cng nh phn ln tanol s dng
lm nhin liu, c sn xut bng cch ln men: khi mt s loi men ru nht
nh (quan trng nht l Saccharomyces cerevisiae) chuyn ha ng trong iu
kin khng c xy (gi l ym kh), chng sn xut ra tanol v cacbon ixt CO2.
Phn ng ha hc tng qut c th vit nh sau:
C6H12O6 2 CH3CH2OH +2 CO2
Qu trnh nui cy men ru theo cc iu kin sn xut ru c gi
l ru. Men ru c th pht trin trong s hin din ca khong 20% ru,
nhng nng ca ru trong cc sn phm cui cng c th tng ln nh chng
ct.
sn xut tanol t cc nguyn liu cha tinh bt nh ht ng cc th tinh
bt u tin phi c chuyn ha thnh ng. Trong vic men bia, theo
truyn thng n c to ra bng cch cho ht ny mm hay mch nha. Trong
qu trnh ny mm, ht to ra cc enzym c chc nng ph v tinh bt to ra
ng. sn xut tanol lm nhin liu, qu trnh thy phn ny ca tinh bt
thnh glucoza c thc hin nhanh chng hn bng cch x l ht vi axt
sulfuric long, enzym nm amylas, hay l t hp ca c hai phng php.
V tim nng, glucoza ln men thnh tanol c th thu c t xenluloza.
Vic thc hin cng ngh ny c th gip chuyn ha mt loi cc ph thi v ph
phm nng nghip cha nhiu xenluloza, chng hn li ng, rm r hay mn
ca thnh cc ngun nng lng ti sinh. Cho n gn y th gi thnh ca cc
enzym cellulas c th thy phn xenluloza l rt cao. Hng Iogen Canada
a vo vn hnh x nghip sn xut tanol trn c s xenluloza u tin vo
nm 2004.
Phn ng thy phn cellulose gm cc bc. Bc 1, thy phn xenluloza
thnh mantoza di tc dng ca men amylaza.
(C6H10O5)n C12H22O11
Bc 2, thy phn tip mantoza thnh glucoza hoc fructoza di tc dng
ca men mantaza.
C12H22O11C6H12O6

94
Bc 3 phn ng ln men ru c xc tc l men zima.
C6H12O6 2 C2H5OH +2 CO2
Vi gi du m tng t nh cc mc gi ca nhng nm thp nin 1990 th
cng ngh hyrat ha tylen l kinh t mt cch ng k hn so vi cng ngh
ln men sn xut tanol tinh khit. S tng cao ca gi du m trong thi gian
gn y, cng vi s khng n nh trong gi c nng phm theo tng nm
lm cho vic d bo gi thnh sn xut tng i ca cng ngh ln men v cng
ngh ha du l rt kh.
Lm tinh khit
i vi hn hp tanol v nc, im si hn hp (azeotrope) cc i nng
96% tanol v 4% nc. V l do ny, chng ct phn on hn hp tanol-
nc (cha t hn 96% tanol) khng th to ra tanol tinh khit hn 96%. V
vy, 95% tanol trong nc l dung mi ph bin nht.
Hai hng cnh tranh nhau c th s dng trong sn xut tanol tinh cht.
ph v im si hn hp nhm thc hin vic chng ct th mt lng
nh benzen c th thm vo, v hn hp li c chng ct phn on mt ln
na. Benzen to ra im si hn hp cp ba vi nc v tanol nhm loi b
tanol ra khi nc, v im si hn hp cp hai vi tanol loi b phn ln
benzen. tanol c to ra khng cha nc. Tuy nhin, mt lng rt nh
(c phn triu benzen vn cn, v th vic s dng tanol i vi ngi c th
gy tn thng cho gan.
Ngoi ra, sng phn t c th s dng hp th c chn lc nc t dung
dch 96% tanol. Zeolit tng hp trong dng vin trn c th s dng, cng nh
l bt yn mch. Hng tip cn bng zeolit l c bit c gi tr, v c kh nng
ti sinh zeolit trong h khp kn v c bn l khng gii hn s ln, thng qua
vic lm kh n vi lung hi CO2nng. tanol tinh cht c sn xut theo cch
ny khng c du tch ca benzen, v c th s dng nh l nhin liu hay thm
ch khi ha tan c th dng lm mnh thm cc loi ru nh ru vang
pooct (c ngun gc B o Nha hay ru vang sherry (c ngun gc Ty
Ban Nha) trong cc hot ng nu ru truyn thng.
S dng

95
tanol c th s dng nh l nhin liu cn (thng thng c trn ln
vi xng) v trong hng lot cc quy trnh cng nghip khc. tanol cng c s
dng trong cc sn phm chng ng lnh v im ng bng thp ca n.
Ti Hoa K, Iowa l bang sn xut tanol cho t vi sn lng ln nht.
N d dng ha tan trong nc theo mi t l vi s gim nh tng th v th
tch khi hai cht ny c trn ln nhau. tanol tinh cht v tanol 95% l
cc dung mi tt, ch t ph bin hn so vi nc mt cht v c s dng trong
cc loi nc hoa, sn v cn thuc. Cc t l khc ca tanol vi nc hay cc
dung mi khc cng c th dng lm dung mi. Cc loi ung cha cn c
hng v khc nhau do c cc hp cht to mi khc nhau c ha tan trong n
trong qu trnh v nu ru. Khi tanol c sn xut nh l ung hn hp
th n l ru ng cc tinh khit.
Dung dch cha 70% tanol ch yu c s dng nh l cht ty u. tanol
cng c s dng trong cc gel v sinh khng khun ph bin nht nng
khong 62%. Kh nng kh trng tt nht ca tanol khi n trong dung dch
khong 70%; nng cao hn hay thp hn ca tanol c kh nng khng khun
km hn. tanol git cht cc vi sinh vt bng cch bin tnh protein ca chng v
ha tan lipit ca chng. N l hiu qu trong vic chng li phn ln cc loi vi
khun v nm cng nh nhiu loi virus, nhng khng hiu qu trong vic chng
li cc bo t vi khun.
Ru vang cha t hn 16% tanol khng t bo v c chng trc vi
khun. Do iu ny, vang Bordeaux thng thng c lm nng thm bng
tanol ti t nht 18% tanol theo th tch ngn chn qu trnh ln men nhm
duy tr ngt v trong vic pha ch lu tr, t thi im n tr thnh c
kh nng ngn chn vi khun pht trin trong ru, cng nh c th lu tr lu
nm trong cc thng g c th 'th', bng cch ny vang Bordeaux c th lu tr
lu nm m khng b hng. Do kh nng st khun ca tanol nn cc ung
cha trn 18% tanol theo th tch c kh nng bo qun lu di.
tanol l ngun nguyn liu ha hc a dng, v trong thi gian qua c
s dng vi phm vi thng mi tng hp hng lot cc mt hng ha cht vi
sn lng ln khc. Hin nay, n c thay th trong nhiu ng dng bng cc
nguyn liu ha du khc r tin hn. Tuy nhin, trn th trng ca cc quc gia
c nn nng nghip pht trin nhng cc c s h tng ca cng nghip ha du
th cn cha pht trin nh Trung Quc, n v Brasil th tanol c th c s

96
dng sn xut cc ha cht m c cc nc phng Ty pht trin sn xut
ch yu t du m, bao gm tylen v butaien.
Cc nguy him
tanol v hn hp ca n vi nc cha trn 50% tanol l cc cht d
chy v d dng bt la.
tanol trong c th ngi c chuyn ha thnh axtalht do
enzym alcohol dehydrogenas phn hy ru v sau thnh axt axtic bi
enzym axtalht dehydrogenasphn hy axtalht. Axtalht l mt
cht c c tnh cao hn so vi tanol. Axtalht cng lin quan ti phn ln
cc triu chng lm sng lin quan ti ru. Ngi ta thy mi lin quan
gia ru v cc nguy c ca bnh x gan, nhiu dng ung th v chng
nghin ru.
Mc d tanol khng phi l cht c c c tnh cao, nhng n c th gy ra
t vong khi nng cn trong mu t ti 0,4%. Nng cn ti 0,5% hoc
cao hn ni chung l dn ti t vong. Nng thm ch thp hn 0,1% c th
sinh ra tnh trng say, nng 0,3-0,4% gy ra tnh tng hn m. Ti nhiu
quc gia c lut iu chnh v nng cn trong mu khi li xe hay khi phi
lm vic vi cc my mc thit b nng, thng thng gii hn di 0,05% ti
0,08%. Ru mtylic hay mtanol l rt c, khng ph thuc l n vo c th
theo cch no (da, h hp, tiu ha).
Ngi ta cng ch ra mi lin quan t l thun gia tanol v s pht trin
ca Acinetobacter baumannii, vi khun gy ra vim phi, vim mng no v
cc vim nhim h bi tit. S pht hin ny l tri ngc vi s nhm ln ph
bin cho rng ung ru c th git cht nhiu loi vi khun gy cc bnh
tryn nhim. (Smith v Snyder, 2005)
2. Etylen Glycol
Etylen glycol c iu ch u tin vo nm 1859 bi nh ha hc ngi
Php Charles Adolphe Wurtz thng qua phn ng x phng ha gia glycol
iacetat vi KOH. Vo nm 1860 iu ch etylen glycol t phn ng hydrat
ha oxid etylen. Trc chin tranh th gii th nht Etylen Glycol khng c
sn xut mt cch rng ri, chin tranh th gii th nht n ra, ti c
etylenglycol c dng nh vt liu sn xut cht n.
Phng php sn xut hin nay

97
Etylenglycol c sn xut t etylen thng qua bc trung gian l to cht
oxid etylen cho phn ng vi nc theo phng trnh ha hc di xc tc l
acid
C2H4O +H2O HOCH2CH2OH
Etylenglycol l cht ch yu dng trong cht chng ng chim trong 40%
trn th trng. Bi v mc cht ny gi r v t cht ny c th ch bin c
nhiu cht c nhiu ng dng.
Cht lm lnh v cht truyn nhit
Etylenhlycol l cht c dng trong cng nghip ch yu l cht truyn nhit
lm lnh trong i lu ca ng c trong ca xe hi hay mn hnh my tnh.
Ngoi ra etylenglycol c dng trong my iu ha v my bm a nhit.
B. PHNG PHP GII TON
VN 1 PHN NG TCH NC CA ALCOL
PHNG PHP
C 2 cch tch nc t ru:
Tch nc sinh alken: Vi ru no n chc phn ng tch nc s sinh ra
alken.
CnH2n+1OH CnH2n + H2O
Nhn xt: Vn dng nh lut bo ton khi lng ta c
nru p = nalken = nnc mru = malken + mnc
Phn ng tch nc ca t 2 ru n chc
2R OH
H
2
SO
4
R O R + H2O

ROH + ROH R O R +H2O
Nhn xt: T phn ng trn ta c nhng nhn xt quan trng sau y
Nu c x ru khc nhau s to ra s ete ti a l :

S ete ti a =
x(x+1)
2
n
H
2
D
= n
ete

1
2
n
alul


98
T 2 cng thc trn ta c h qu nh sau :
- nru 1 =nru 2 =nru 3 ==nru n n
mi ete
=
n
ete
n
=
n
H
2
D
n

- V hin nhin s khng th b qua c nh lut bo ton khi lng :
mru =mete + m
H
2
O

- Mt nhn xt v cng quan trng m thng thng chng ta qun : Oxy trong
ete lun gn trn Carbon no.
V d : S khng tn ti dng ete : CH3 CH2 =CH O CH2 CH3
VN 2 PHN NG CA RU VI KIM LOI KIM
PHNG PHP
Phng trnh tng qut ca r tc dng vi kim loi kim :
R(OH)n + Na R(ONa)n +
n
2
H2
Nu ta gi nr l s mol ru, Mr l khi lng phn t trung bnh ca ru,
khi lng ca ru ban u l mr. T phng trnh ta c nhng h thc
quan trng.

n
n
H
2
=
2
n

m
n
H
2
=
2
n
M
r
=
m
2n
H
2
*n

Thng qua cng thc trn ta c th bin lun v xc nh cng thc phn t
ca ru.
Vn dng phng php tng gim khi lng ta c th suy ra mt cng thc.
Nu khi lng mui to thnh c khi lng phn t l MY, th lc ta c :
MY =MX +(23 n)
mY =mX +(23 n)nr

VN 3 NHN BIT RU N CHC VI RU A CHC
PHNG PHP
Ru a chc c cc nhm OH k cn th s tham gia phn ng vi Cu(OH)2
to dung dch phc mu xanh thm (xem li phn ng c trng ca ru a
chc). Ru n chc khng c phn ng ny.
VN 4 PHN NG ESTE HA CA RU
PHNG PHP
Dng bi ton ny thng lin quan n hiu sut phn ng nn ta c th tnh
ton thng qua hiu sut phn ng.

99
ru =
V
r
V
dd
*100
Cng nh c nhn ta c cu : Ty c m ng bin La cm m gp mm.
Bi ton ha hc l mun mu mun v, do vy gii quyt mt bi ton
iu u tin chng ta ai cng bit l phi c kin thc c bn.
Phn ng este ha dng tng qut :
mR(OH)n + nR(COOH)m Rm - (COO)m.n Rn + m.nH2O
i vi dng ton ny khng c ci mc chung no thit lp cng thc, ch
bit chng ta s vn dng nhng cng c gii ton hu hiu sau :
+Hiu sut : H =
Ing thc t
Ing I thuyt
*100%
+Vn dng nh lut bo ton khi lng
+Vn dng k thut gii ton v kin thc c bn.
VN 5 RU
PHNG PHP
ru l s mL ru etylic c trong 100mL hn hp ru vi nc

VN 6 PHN NG OXY HA RU
PHNG PHP
Dng bi ton ch yu xoay quanh oxy ha ru bc 1
Phng trnh tng qut : R(CH2 OH )m+mCuO
t
0
C
== R(CHO)m +mCu +nH2O
X(mX, MX) T(mT) Y (mY, MY) S(mS)
Vi trng hp c bit : CH3OH
CuO,t
0
C
====== HCHO
Phng php dng bi ton oxy ha ru bc 1 ch yu l phng php tng
gim khi lng.

100
Do tc nhn [O] trong CuO ly mt 2mH trong ru nn lc khi lng
phn t MX s gim i 2m.
MY =MX 2m
Mt khc lng rn sau phn ng s b gim i 16g bi s kt hp ca [O] vi
2H ca ru
mrn T =mrn S +16m.nX p
T cng thc trn ta c cng thc h qu nh sau :
m = mrn T - mrn S =16m.nX p
Lu : Nu m = 1 (ru n chc) th cng thc trn ta d dng suy ra c
cc gi tr cn tm.
BI TP
Bi 1 Cho 23 gam alcol X tc dng vi Na d thu c 8,4 lt H2 (ktc). Bit phn
t khi ca MX <120. Tm cng thc ca X .
Gii
Phn tch : V bi cha cho bit ru em phn ng vi Na l ru n chc
hay a chc, nn chng ta c gi theo cng thc tng qut ca ru R(OH)n
p dng cng thc m chng ta chng minh phn phng php gii
MX =
m
X
2n
H
2
*n =
23
2
8,4
22,4
*n =
92
3
n <120 n < 3,91
Vi MX, n l nguyn nn n ch nhn gi tr l 3 MX =92g/ mol CTPT ru a
chc l C3H5 (OH)3
Bi 2 t chy 0,7 mol mt alcol mch h thy cn ng 2,8 mol O2,. Xc nh
cng thc cu to ca alcol v gi tn chng.
Gii
Phn tch : bi cha ni r cho ta bit l alcol mch h trn l n chc hay
a chc, no hay cha no. Cho nn ta ngh n cch gi CTPT ca ru l R(OH)n,
nhng cng thc ny ch hiu qu khi ru th hin tnh cht ha hc. Cn i

101
vi qu trnh t chy mt cht m cha bit r s chc ca n, th tt nht cc
bn nn gi theo cng thc tng qut CxHyOz. vi iu kin ca x,y,z nh th no
(cc bn nn c li bi 1) ta lun c nhng iu kin sau :
_
1 z x
y 2x +2
(*)
91CxHyOz +(x+
y
4
-
z
2
) O2 xCO2 +
y
2
H2
Theo bi ra ta c:
n
CO
2
n
ru
=
2,8
0,7
=4 x+
y
4
-
z
2
=4 4x + y 2z =16 (1)
T (1) ta c: 4x9 +y =16 +2z 16 + 2.1 = 18 (theo iu kin (*))x
18-
4

Theo iu kin (*) y 2x+2 - y - (2x+2) x
18-2x-2
4
x
8
3
(2)
Mt khc theo (*) ta c: 4x +y 2z =16 4x + 2x + 2 2z 16 4x + 2(x z) 14
V x z x <
14
4
=3,5 (3) (x, y, z Z) x = 3
Vy vi x =3 y = 4 + 2z (y 2x+2 = 8) z 2
z y CTPT ru
1 6 C3H6O
2 8 C3H8O2

Nhn xt i vi nhng dng bi ton nh th ny (ngha l d kin t hn n) th
chng ta phi vn dng trit cc tnh cht ca Hydro v Carbon. Bn cnh cng
cn nm vng th thut ton hc, gii quyt mt cch nhanh chng.
Bi 3 Hn hp gm 3 alcol X, Y , Z c khi lng nhau. em t chy mi ru trn
th nhn thy n
CO
2
: n
H
2
O
=3: 4.
CTPT ca X, Y, Z ln lt l:
A. C2H6O, C3H8O, C4H10O C. C3H8O, C3H8O2, C3H8O3
B. C3H8O, C4H10O, C5H8O D. C3H6O, C3H6O, C3H6O3
Gii

102
Phn tch Nh bi m u ti gii thiu, i vi vic t 1 cht hu c sinh ra s
mol CO2 v H2O ta ch vic p dng cng thc lin quan (cc bn xem li bi 1).
S C
S H
=
n
CD
2
2n
H
2
D
; nhchc =
n
H
2
D
-n
CD
2
1-h

Vy nu p dng cng thc trn th rt d dng suy ra c p n C.
Bi 4 Khi tch H
2
O t ancol n chc A iu kin thch hp th thu c cht hu c
D c tkhi i v i A bng 1,7. Ancol A l
A. CH
3
OH B.C
3
H
5
OH C. C
2
H
5
OH D. C
3
H
7
OH
Gii
Phn tch: Da vo bi v d kin ta nhn thy r y l phn ng tch nc ca
ru sinh ra ete (V MD >MA). CTPT ca ete c dng R O R CTPT ru ROH
Theo bi ra ta c:
2R +16
R+17
=1,7 R = 43 (C3H7 - ) ru C3H7OH
Bi 5 [Khi B 2008] un nng gm hn hp 2 ru no n chc mch h k tip
nhau trong dy ng ng vi H2SO4 c 140
0
C. Sau khi kt thc phn ng thu
c 6 gam hn hp gm 3 ete v 1,8 gam H2O. CTPT ca 2 ru trn l:
A. CH3OH v C2H5OH C. C3H5OH v C4H7OH
B. C2H5OH v C3H7OH D. C3H7OH v C4H9OH
Gii
Ta c: n
H
2
O
=
1,8
18
=0,1mol nr =0,2mol
p dng nh lut bo ton khi lng: mru =mete +mnc =6 +1,8 =7,8 gam
M
ru =
7,8
0,2
=39 a p a n A (Tnh cht gi tr trung bnh).
Bi 6 [Khi A 2009] X phng ha hon ton 66,6 gam gm hai 2 este HCOOC2H5
v CH3COOCH3 bng dung dch NaOH, thu c hn hp X gm 2 alcol. ung nng
hn hp X vi H2SO4 c, 140
0
C, sau khi phn ng hon ton thu c m gam
nc. Gi tr m l
A. 18 gam C. 16,02 gam
B. 8,10 gam D. 4,05 gam

103
Gii
Phn tch : bi ni rt r l phn ng x phng ha hon ton hn hp 2este no
n chc 2 ru no n chc l CH3OH, C2H5OH. Nu cc bn nhanh s nhn
thy rng 2 este ny c cng khi lng phn t. Rt d dng tnh c tng s
mol ca hn hp 2 este tng s mol hn hp ru. M theo phng php gii nu
tnh c tng s mol ru Tng s mol nc v ete
T nhng phn tch trn ta d dng tnh c
nhh este =
66,6
74
=0,9 mol =nX m = 18*
0,9
2
=8,10 gam a p a n B
Bi 7 [Khi A 2012] Trong alcol X, oxy chim 26,67% v khi lng. un X vi
H2SO4 c nng thu c alken Y. Phn t khi ca Y l :
A. 56. B. 70. C. 28. D. 42.
Gii
Phn tch: Ru X tch nc alken ru no n chc CTPT ca X CnH2n+1OH
%mO =
16
14n+17
*100 =26,67 n =3 X l C3H7OH Y l C3H6 (42) a p a n D
Bi 8 [Khi B 2012] Oxi ha 0,08 mol mt ancol n chc, thu c hn hp X
gm mt axit cacboxylic, mt anehit, ancol d v nc. Ngng t ton b X ri chia
lm hai phn bng nhau. Phn mt cho tc dng ht vi Na d, thu c 0,504 lt kh
H2 (ktc). Phn hai cho phn ng trng bc hon ton thu c 9,72 gam Ag. Phn
trm khi lng ancol b oxi ha l
A. 50,00% B. 62,50% C. 31,25% D. 40,00%
Gii
Phn tch: bi cho bit rt r hn hp X gm acid, aldehyd, ancol, nc. T
nu bi ny chng ta t n gii h phng trnh (theo phng php i s) th
chng ta mt nhiu thi gian. Chng ta rng, khi ru oxy ha ru n chc
ra aldehyd hay acid th ta lun c: n
H
2
O
=nacid =naldehyd
n
ru d
+n
H
2
O
=nru p
Khi aldehyd n chc phn ng trng gng s xy ra hai trng hp:

104
Nu aldehyd em tham gia phn ng trng gng l aldehyd formic th ta lun c:
nHCHO =4nAg
Nu l aldehyd n chc khc: naldehyd =2nAg
T nhng phn tch trn ta d dng gii quyt bi ton:
V chia hn hp X thnh hai phn bng nhau Xem nh alcol tham gia phn ng
mi phn l: 0,04 mol
1
2
hn hp X +Na H2 (gm nc, acid, ru d phn ng)
(n
H
2
=
0,504
22,4
=0,0225mol) nacid =2n
H
2
0,04 =0,005 mol (xem li phn tch)
1
2
hn hp X phn ng trng bc Ag (nAg =
9,72
108
=0,09 mol)
Nu X l RCHO naldehyd =
1
2
nAg =0,045 >0,04 loi Aldehyd l HCHO v acid s
l HCOOH cng tham gia phn ng trng bc naldehyd =
n
Ag
- 2n
ccid
4
=
0,09-20,05
4
=0,02
%malcol p =
n
ccid+n
cldchjd

0,04
=
0,005+0,02
0,04
*100% =62,5% a p a n B
Bi 9 [Khi B 2012] un nng m gam hn hp X gm cc cht c cng mt loi
nhm chc vi 600 ml dung dch NaOH 1,15M, thu c dung dch Y cha mui ca
mt axit cacboxylic n chc v 15,4 gam hi Z gm cc ancol. Cho ton b Z tc
dng vi Na d, thu c 5,04 lt kh H2 (ktc). C cn dung dch Y, nung nng cht
rn thu c vi CaO cho n khi phn ng xy ra hon ton, thu c 7,2 gam mt
cht kh. Gi tr ca m l
A. 40,60 B. 22,60 C. 34,30 D. 34,51
Gii
Phn tch: V hn hp X c cc cht ng chc vi nhau (ngha l s chc bng
nhau) acid n chc alcol cng n chc. Chng ta cn lu phn ng
RCOONa + NaOH
Cu0,t
0
C
-- Na2CO3 +RH (xem li bi Alkan)
T nhng phn tch trn ta gii quyt bi ton nh sau:
Gi cng thc phn t trung bnh ca X l RCOOR

Nu0H
-- RCOONa +R
OH

105
R
OH +Na
1
2
H2 nX = nZ =nNaOH p =nY =2*
5,04
22,4
=0,45 mol
nNaOH phn ng vi mui RCOONa =0,6*1,15 0,45 =0,24 mol =nRH
R + 1 =
7,2
0,24
=30 R C2H6 - acid trn l C2H6COOH CTPT X: C2H6COOR

Bo ton khi lng : mX +mNaOH p =mmui +mZ
mx =96.0,45 +15,4 - 40*0,45 =40,6 gam a p a n A
Bi 10 [Khi B 2012] Cho hn hp X gm ancol metylic, etylen glicol v glixerol.
t chy hon ton m gam X thu c 6,72 lt kh CO2 (ktc). Cng m gam X trn cho
tc dng vi Na d thu c ti a V lt kh H2 (ktc). Gi tr ca V l
A. 3,36 B. 11,20 C. 5,60 D. 6,72
Gii
Phn tch: Bi ny rt th v, nu cc em khng bnh tnh s mt nhiu thi gian
bi ny. tng ca ngi ra cng rt c o, cho 3 ru phn vi s nhm
chc tng dn. em t chy bit c s mol ca CO2, nu em 3 ru ny phn
ng vi Na d thu c V =?
Nhn xt: Mi ru no (a chc, n chc) ta lun c S C S O
ba cht cho trn ta nhn thy mt iu rng: C 3 cht u c s C bng s O.
M O y l nhm nh chc co bao nhiu O co by nhiu Hchc
T nhng nhn xt trn ta suy ra: n
C
X
=n
0
X
=n
C0
2
=
6,72
22,4
=0,3 mol
V =
22,40,3
2
=3,36 lt p n A
Bi 11 [Khi B 2008] Cho m gam mt alcol no n chc X qua bnh ng CuO
nung nng d. Sau khi phn ng hon ton, khi lng cht rn gim 0,32 gam. Hn
hp thu c c t khi i vi H2 l 15,5. Gi tr ca m l:
A. 0,46 B. 0,64 C. 0,92 D. 0,32
Gii
Phn tch: Bi ny c hng dn mc phng php gii, cc bn xem li.
y chng ta s chng minh cng thc tnh m

106
m = (4*dhh
H
2
16)*
m
1

Chng minh cng thc ny tht n gin, da vo phng php gii ta chng
minh c MX =MY +2 (1)vi s mol tham gia phn ng chnh l s mol ca O trong
CuO b ly i m = (MY +2)
m
1
(2)
Ta s i tm MY da vo t khi hi hn hp, vi lu nh phng php nu
nY =nnc Mhh =
M
Y
+18
2
=2*dhh
H
2
MY =4dhh
H
2
18 (3). T (3) th vo (2) ta c
cng thc ng khung nh trn.
T cng thc ng khung ta suy ra c kt qu ca bi ton:
m =(4*15,5 16)*
0,32
16
=0,92 gam a p a n C
Bi 12 Cho mt ancol no n chc qua bnh dng CuO(d) nung nng. Sau khi phn
ng hon tan khi lng cht rn trong bnh gim 0,64g. Hn hp hi thu c c
t khi i vi H2 l 19. t ht lng ru trn ri dn sn phm chy vo bnh dd
NaOH d thy khi lng bnh NaOH tng m gam. Gi tr ca m l?
Gii
p dng cng thc chng minh bi 11 mru =(4*19 16)*
0,64
16
=2,4 gam
Mru =
2,4
0,64
16
=60 CTPT ca ru l: C3H7OH vi s mol l 0,04 mol
T y d dng tnh c khi lng bnh NaOH tng ln chnh l khi lng ca
CO2 v H2O. m = 3*0,04*44 + 4*0,04*18 = 8,16 gam.
Bi 13 Cho m gam hn hp X gm hai ru (ancol) no, n chc, k tip nhau trong
dy ng ng tc dng vi CuO (d) nung nng, thu c mt hn hp rn Z v
mt hn hp hi Y (c t khi hi so vi H2 l 13,75). Cho ton b Y phn ng vi
mt lng d Ag2O (hoc AgNO3) trong dung dch NH3 un nng, sinh ra 64,8 gam
Ag. Gi tr ca m l
A. 7,8. B. 8,8. C. 7,4. D. 9,2.
Gii

107
Phn tch: y l bi p dng thun ty vo phng php gii nu trn, mun
tm c m iu u tin ta phi xc nh c cng thc ca 2 ru, v tm c
s mol ca 2 ru.
Ta d dng tnh c phn t khi trung bnh ca ru da vo cng thc bi 11
MX =MY +2 =4*13,75 16 =39 CTPT ca 2 ru l: CH3OH v C2H5OH
Quy tc ng cho ta suy ra
M =32 7
39 nmetylic =netylic

M =46 7
Hai aldehyd tng ng l: HCHO v CH3CHO sinh ra s mol bc tng ng theo t l
2:4 nmi ru =
64,8
1086
=0,1 mol m = 39*0,2 = 7,8g a p a n A
Bi 14 Cho 10mL alcol etylic 92
0
tc dng ht vi Na thu c V lt (ktc). Bit khi
lng ring ca nc l 1g/ mL v ca ru l 0,8g/mL. Xc nh V
Gii
Theo cng thc ru: ru =
V
r
V
dd
*100 =92 Vr =9,2mL nnc =0,8mL
mr =0,92*0,8 =0,736g nr =0,016 mol ; mnc =0,8*1 =0,8g nnc =0,044mol
n
H
2
=
1
2
*(0,016+0,044)=0,0644mol V = 1,354 lt
Bi 15 T l th tch CO2 v H2O bin i nh th no nu t chy ng ng bng
cc alcol metylic.
Gii
V l ng ng ca ru metylic Dy ng ng l ru no CTPT CnH2n+2O
Phng trnh phn ng t chy :
CnH2n+2O +
3n
2
O2 nCO2 +(n+1)H2O

108
Lp t s T =
n
H
2
O
n
CO
2
=
n+1
n
=1 +
1
n
(v n 1) lim
n
T =1 1< T 2
Vy khi t chy ru no n chc ta lun c : 1<T 2 Vi T =
n
H
2
O
n
CO
2

Lu : y chnh l cng thc m chng ta c th p dng trc tip bin lun bi
ton, khi t chy ru no n chc. (Cng p dng c cho ru no a chc).
Bi 16 [C Khi A 2008] t chy hon ton mt ru (ancol) a chc, mch h
X, thu c H2O v CO2 vi t l s mol tng ng l 3:2. Cng thc phn t ca X.
Gii
Phn tch: y bi ton ni rt r l t chy mt ru a chc (cha ni r no
hay khng no). Nhng ta da vo bi 15 ta xc nh c ru no hay cha no. Th
hai nu xc nh c X ta phi da vo cng thc T =
n
H
2
O
n
CO
2
=
n+1
n

V bi cho bit T =3 :2 =1,5 (1 ;2] Alcol em t chnh l ru no a chc

n+1
n
=
3
2
n =2 CTPT ca ru no a chc : C2H4(OH)2 (Etylenglycol).
Bi 17 [Khi A 2008]: Khi phn tch thnh phn mt ru (ancol) n chc X th
thu c kt qu: tng khi lng ca cacbon v hiro gp 3,625 ln khi lng oxi.
S ng phn ru (ancol) ng vi cng thc phn t ca X l?
Gii
Phn tch: Bi ny ni rt r, ru em t chy l ru n chc CTPT ca
ru l R OH. xc nh c cng thc ca ru ta ch cn da vo d kin
Tng khi lng ca carbon v hydro gp 3,625 ln khi lng oxy (trong phn t
X ch c mt oxy).
Theo bi ra ta c: Ru s c cng thc phn t dng: CxHyO (y 2x+2) (1)
12x+y =3,625*16 = 58 (y 2x+2) x = 4 v y =10 l cp nghim ph hp.
CTPT ca ru X l: C4H10O.
Bi 18 [Khi A 2010] Hn hp M gm ancol no, n chc X v axit cacboxylic n
chc Y, u mch h v c cng s nguyn t C, tng s mol ca hai cht l 0,5 mol
(s mol ca Y ln hn s mol ca X). Nu t chy hon ton M th thu c 33,6 lt

109
kh CO2 (ktc) v 25,2 gam H2O. Mt khc, nu un nng M vi H2SO4 c thc
hin phn ng este ho (hiu sut l 80%) th s gam este thu c l:
A. 22,80 B. 34,20. C. 27,36. D. 18,24
Gii
Phn tch: Bi cho bit ru X l ru no n chc, nhng cha cho bit acid
carboxylic Y l no hay cha no. Nhng bi cho bit hai cht ny cng s C S
Carbon trung bnh trong hn hp M chnh l s Carbon trong X v Y (Tnh cht gi tr
trung bnh). Ci mu cht y l chng ta phi tm c CTPT ca Y, nhng bi
ton li cha cho chng ta bit Y l no hay cha no. tm c Y l no hay cha no
ta da vo cng thc m chng ta khng bao gi qun. t chy mi hp cht hu
c ta lun c:
nhchc =
n
H
2
D
-n
CD
2
1-h

T cng thc ny m ta d dng tm ra c s lin kt c trong Y.
T nhng phn tch trn ta gii quyt nhanh chng bi ton nh sau:
S C
M =
n
CO
2
n
M
=
33,6
22,4
0,5
=3 Trong X v Y u c 3C CTPT ca ru X: C3H7OH.
p dng cng thc t chy ta c:
0,5 =
2S,2
18
-
33,6
22,4
1-k
=1,2 iu ny chng t rng Y l mt acid carboxylic cha no.

Hoc ta c th l lun nh sau: V khi t chy hn hp M th X t chy lun c
n
CO
2
<n
H
2
O
;m bi cho bit n
CO
2
>n
H
2
O
Acid l cha no n chc mch h.
n y ta vn tnh cht gi tr trung bnh v th thut ton hc.
Gi k1, k2 l s lin kt c trong X v Y k1 =0. Theo tnh cht gi tr trung bnh ta
c: k2*nY =1,2*0,5 k2*nY =0,6 (1) (Vi nY >nX; nX +nY =0,5, k2 nguyn) 2nY >0,5
0,25 < nY <0,5 1,2 < k2 <2,4 k2 =2 CTPT Y: C2H3COOH (acid acrylic).
nY =0,3 nX =0,2 (mol)
C3H7OH +C2H3COOH C2H3COOC3H7 +H2O

110
S gam este thu c l: 0,2*0,8* 114 =18,24 gam a p a n D.
Bi 19 [Khi B 2010] t chy hon ton mt lng hn hp X gm 2 ancol (u
no, a chc, mch h, c cng s nhm -OH) cn va V lt kh O2, thu c 11,2 lt
kh CO2 v 12,6 gam H2O (cc th tch kh o ktc). Gi tr ca V l
A. 11,20. B. 4,48. C. 14,56. D. 15,68
Gii
Phn tch: Ru no a chc c cng s nhm OH nn khi t chy lun c
n
CO
2
<n
H
2
O
nX =n
H
2
O
n
CO
2
=
12,6
18
-
11,2
22,4
=0,2. Do vy ta s d dng tm ra c
CTPT ca ru tm ra c s nhm OH (ngha l tm ra c s O trong X).
S C
X =
n
CO
2
n
X
=
0,5
0,2
=2,5 Tnh cht gi tr trung bnh ta c:
Ru a chc th nht l C2H4(OH)2 CTPT tng ng ca hn hp X: C2,5H7O2
t hn hp X: C2,5H7O2 +3,25 O2 2,5CO2 +3,5H2O
V = 3,25*0,2*22,4 = 14,56 lt a p a n C
Bi 20 [Khi B 2010] t chy hon ton m gam hn hp X gm ba ancol (n
chc, thuc cng dy ng ng), thu c 8,96 lt kh CO2 (ktc) v 11,7 gam H2O.
Mt khc, nu un nng m gam X vi H2SO4 c th tng khi lng ete ti a thu
c l :
A. 5,60 gam. B. 6,50 gam. C. 7,85 gam. D. 7,40 gam.
Gii
Phn tch: bi cha cho bit hn hp 3 alcol trn l no hay cha no, nhng
cho ta bit c s mol H2O v CO2 Xa c nh c dy ng ng ca hn hp X.
y c 3 ru s to s ete ti a l:
n(n+1)
2
=6 vi s mol bng na s mol ru
n
CO
2
=
8,96
22,4
=0,4 mol; n
H
2
O
=
11,7
18
=0,65 mol n
CO
2
<n
H
2
O
Hn hp X thuc Alkanol
CTPTTB ca hn hp X c dng: C
n
H
2n+2
O vi nX =n
H
2
O
- n
CO
2
=0,65 0,4 =0,25

111
S C
=
n
CO
2
n
X
=
0,4
0,25
=1,6 CTPTTB ca X l: C1,6H5,2O.
CTPTTB ca ete l (C1,6H4,2)2O mete =62,8*
0,25
2
=7,85gam a p a n C.
Bi 21 [Khi A 2009] t chy hon ton 0,2 mol mt ancol X no, mch h cn va
17,92 lt kh O2 ( ktc). Mt khc, nu cho 0,1 mol X tc dng va vi m gam
Cu(OH)2 th to thnh dung dch c mu xanh lam. Gi tr ca m v tn gi ca X
tng ng l
A. 9,8 v propan-1,2-iol. B. 4,9 v propan-1,2-iol.
C. 4,9 v propan-1,3-iol. D. 4,9 v glixerol.
Gii
Phn tch: bi cho bit alcol X em t chy l alcol a chc no
CTPT X: CnH2n+2Ox, da vo s mol oxy em t chy ta c th tnh ra s CX
Bin lun CTPT ca ru v tnh ton thng qua phn ng to phc
Lu : 2 nhm OH k cn nhau mi cho phn ng to phc loi p n C
C 4 p n u c p n ru l 3C ch tm x trong ru
nX =2n
(CuOH)
2
n
(CuOH)
2
=0,05 m
(CuOH)
2
=98*0,05 =4,9g loi A
Ta c: n
O
2
=
17,92
22,4
=0,8mol
n
O
2
n
X
=
0,8
0,2
=4
3n+1-x
2
=4 3*3 +1 x =8 x = 2
Vy X l propan1,2-diol. a p a n B
Bi 22 [Khi A 2009] Khi t chy hon ton m gam hn hp hai ancol no, n
chc, mch h thu c V lt kh CO2 ( ktc)v a gam H2O. Biu thc lin h gia m,
a v V? Gii
Phn tch: y l dng ton quen thuc ca phn ng t chy, chng ta c th dng
phng php bo ton nguyn t gii quyt nhanh chng. (Cc bn c th dng
phng php 3 dng gii quyt bi ton).
t chy ru no n chc (Dng CnH2n+2O) ta lun c cng thc sau:
m =a -
V
5,6

m
C
n
H
2n+2
O
=m
H
2
O
4 n
CO
2


112
Bi 10 PHENOL (C6H5OH)
A. KIN THC C BN
I. L TNH V C CU PHENOL
1. L tnh
o Phenol l cht rn mu trng, d b oxy ha
thnh mu hng nht.
o nhit thng, t tan trong nc, khi
nhit t
0
=70
0
C tan nhiu trong nc.
o c tnh, c tnh st trng, lm bng da nng.
o Nhit nng chy: t
0
=43
0
C.
o im si ca phenol: t
0
=181,7
0
C.
im si ca phenol cao hn cc hydrocarbon
cng C l do phenol c th to c lin kt hydro
lin phn t.

2. C cu
o Phenol l tn gi chung dng ch nhm hp cht c
cng thc tng qut l ArOH (Ar: Aromatic: vng
thm). Vi Ar l mt hay nhiu nhn hng phng, c
hoc khng c nhm th.
o Trong phenol nhm hydroxyl ni trc tip vi Carbon
sp
2
ca nhn hng phng.
o Phenol c tnh cng hng ngoi, do ni n C O ch c 136pm,
so vi C O trong MeOH l 142pm.


113
CH
2
-OH
benzylic
CH
2
-CH
2
-OH
phenyletylic

o Nhiu c tnh phn nh phenol cho phn ng cng hng ngoi, s
ngn i ca ni C O nh:
OH ca nhm phenol t tnh baz.
Hydrogen ca nhm OH c nhiu tnh acid hn
Tc cht tc kch vo vng hng phng ti v tr orto v para
nhanh hn so vi benzen.
3. Phn bit ru thm v phenol.
Phenol l hp cht hu c trong cng thc cu to c nhm OH lin kt trc
tip vi nhn hng phng.
V d:

Ru thm l hp cht hu c trong cng thc cu to c nhm OH lin kt
trc tip mch nhnh ca nhn hng phng.

II. DANH PHP
1. Tn thng thng
Hu ht cc phenol hin din trong t nhin u c tn thng thng.


114

2. Danh php IUPAC
a. Trong trng hp Ar-OH c mt vng hng phng
Chn phenol lm tn tc, vi carbon mang nhm chc hydroxy nh s 1.
V d:

b. Tn nhm th
Trong trng hp trn vng hng phng c nhm th nh chc khc u
tin hn phenol. Lc nhm chc OH (hydroxyl) ch c gi l nhm th -
hydroxy trong tn hp cht.

115
OH
COOH
Acid4-hydroxybenzoic
V d:

III. TNH CHT HA HC
1. Phn ng th ca nguyn t H nhm OH.
a. Phn ng vi kim loi kim.

+
1
2
H2

b. Phn ng vi dung dch kim

Phenol c Ka =1,3.10
-10
nh hn Ka1 nhng ln hn Ka2 ca acid carbonic
H2CO3 (K1 =4,5.10
-7
; K2 =4,7.10
-11
). Nn H2CO3 c th y phenol ra khi
phenolatnatri to ra mui NaHCO3 (khng to mui Na2CO3).
C6H5ONa + H2O + CO2 C6H5OH +NaHCO3

116
OH
+ 3Br
2
OH
Br
Br
Br
2,4,6-Tribromophenol
+ 3HBr
c. Phn ng nhn bit phenol
Phenolat ca st to phc c mu tm dung nhn bit phenol
C6H5OH + FeCl3 [Fe(OC6H5)6]
3+
+6H
+
+ 3Cl
-

(phc mu tm)
2. Phn ng th ca nhn hng phng
Phenol tham gia phn ng th d hn benzen v hydrocarbon thm , do trn
vng benzen c mt electron tng ln, c bit ti v tr o, p- nn cc tr
c nh hng cho cc sn phm chnh.
a. Tc dng vi dung dch brom ngay nhit thng.

(Kt ta trng).
Phn ng cng tng t cho dung dch Cl2
Iod khng tham gia phn ng th vi phenol.
b. Tc dng vi dung dch HNO3 c
Phenol tc dng vi dung dch HNO3 c to ra kt ta cam


117
c. Phn ng trng ngng vi formaldehyd poly phenolformaldehyd.

IV. IU CH PHENOL
1. i t Benzen

2. i t Cumen

3. i t nha than .
Phenol c iu ch t nha than , trong qu trnh chng ct
du m.
4. i t mui arensulfonat natrium.


118
V. VN CN BIT
1. Lch s ra i
Phenol c pht hin vo nm 1834, khi n c chit xut t nha
than , vn l ngun chnh cho n khi s pht trin ca ngnh cng
nghip ha du. Cc cht st trng c tnh ca phenol c s dng bi Sir
Joseph Lister (1827-1912) trong k thut phu thut tin phong ca ng v
cht kh trng, mc d kch ng da do tip xc lin tc vi phenol cui cng
dn n vic thay th v khun (vi trng min ph) cc k thut trong phu
thut. Lister quyt nh rng nhng vt thng mnh phi c ra sch.
ng sau c ph nhng vt thng vi mt ming gi hoc lint c bo
him trong carbolic acid. N cng l thnh phn hot cht trong mt s thuc
gim au ng ung nh Chloraseptic phun cng nh Carmex . Phenol cng
l thnh phn chnh ca khi carbolic Ball , mt thit b trn th trng ti
London vo th k 19 nh l bo v ngi s dng chng li bnh cm v cc
bnh khc. Th chin th hai Tim phenol c i khi c s dng nh mt
phng tin nhanh chng thc hin . c bit, phenol c s dng nh mt
phng tin git ngi ca c quc x trong th chin th hai . c s
dng bi c quc x vo nm 1939 nh mt phn ca n git cht m du
chng trnh, phenol, r tin v d lm v nhanh chng gy cht ngi, tr
thnh c t tim ca s la chn thng qua nhng ngy cui cng ca cuc
chin. Mc d Zyklon-B bt vin, pht minh bi Gerhard Lenz , c s dng
trong cc phng hi ngt tiu dit cc nhm ln ca ngi dn, pht xt
c c bit rng tiu dit ca cc nhm nh hn l kinh t hn thng qua
tim ca tng nn nhn, mt lc, vi phenol. tim Phenol c trao cho hng
ngn ngi dn trong cc tri tp trung , c bit l Auschwitz-Birkenau .
Khong mt gram l gy t vong. Tim c qun l bi bc s y
khoa , h tr l , hoc i khi cc bc s t nhn; tim nh ban u c tim
tnh mch , thng cnh tay, nhng tim trc tip vo tim , to ra gn
nh ngay lp tc ci cht sau c thng qua. Mt trong nhng t nhn
ni ting s c thc hin vi mt liu tim phenol ti Auschwitz l
Thnh Maximilian Kolbe , mt linh mc Cng gio ngi tnh nguyn tri qua
ba tun v i v mt nc vo v tr ca t nhn khc.
2. ng dng
Phenol c dng trong nhiu lnh vc khc nhau:

119
Cng nghip cht do: phenol l nguyn liu iu ch
nha phenol formaldehyde.
Cng nghip t ha hc: T phenol tng hp ra t polyamide.
Nng dc: T phenol iu ch c cht dit c di v kch
thch t thc vt 2,4 - D ( l mui natri ca axit 2,4 dicloacetic).
Phenol cng l nguyn liu iu ch mt s phm nhum,
thuc n (acid picric).
Do c tnh dit khun nn phenol c dng trc tip lm
cht st trng, ty u, hoc iu ch cc cht dit nm
mc (ortho - v para - nitrophenol)
B. PHNG PHP GII TON
VN 1 XC NH S NHM OH PHENOL V ALCOL THM
PHNG PHP
c tnh ca ru thm v phenol khc nhau ch ru thm ch tc dng
c vi Na (ch th hin tnh cht ca ru thng thng). Cn i vi
Phenol th n c th tc dng c vi c Na ln NaOH.
Gi cng thc tng qut ca cc chc OH gn trc tip vo vng v trn dy
nhnh CTPT tng qut c dng: R(OH)n+m _
n nhmOH gn trn vng
m nhmOH gn trn nhnh

o Khi tc dng trc tip vi Na th c hai u phn ng
R(OH)n+m + (m+nNa R(ONa)m+n +
m+n
2
H2
o Khi tc dng vi NaOH ch c OH gn trn nhn tham gia phn ng:
R(OH)m+n + nNaOH R(OH)m(ONa)n +nH2O.
T y ta thit lp mt h phng trnh gii m v n.
n
H
2
n
A
=
m+n
2

n
NaDH
n
A
= n

VN 2 PHN NG NITRO HA BROM HA
Phn ng nitro ha bng dung dch HNO3 m c acid picric co kt ta
mu cam.


120
Da vo phn ng c nhng dng ton sau:
Hiu sut phn ng nitro ha:
H% =
m
thc t

m
I thuyt
*100%

o mthc t : Khi lng ca acid picric m ta thu c
o ml thuyt: Khi lng acid picric tnh theo phng trnh phn ng.
Tnh khi lng ca acid picric thu c
o Ta lp t s:

Nu
n
henoI
1
<
n
HNO
3
3
Tnh theo s mol ca cht ht l phenol.
macid picric = 229*nphenol

Nu
n
henoI
1
>
n
henoI
1
Tnh theo s mol acid nitric
macid picric =
229
3
*n
HND
3

i vi phn ng ca brom cng tnh ton tng t.
VN 3 NHN BIT PHENOL
PHNG PHP
Nu trong hp cht nhn bit c cc nhn hng phng, gn vi cc nhm
chc khc nhau. Th ta dng phn ng, nhn bit c trng ca phenol vi
Fe
3+
Phc mu tm
C6H5OH + FeCl3 [Fe(OC6H5)6]
3+
+6H
+
+ 3Cl
-

(phc mu tm)
Nu trong hp cht khng cha nhn hng phng, th ta dng phn ng
nhn bit ca phenol kt ta trng vi dd Br2 hoc kt ta vng vi dd HNO3.

n
henoI
1
v
n
HNO
3
3


121
C. BI TP
Bi 1 t chy 5,8 gam cht A thu c 2,65 gam Na2CO3, 2,25 gam H2O v 12,1
gam CO2. Bit rng 1 phn t ca cht A ch cha 1 nguyn t oxy. Cho kh CO2
sc vo dung dch A ch thu c cht B l mt dn xut ca benzen. trung
ha a gam hn hp B v mt ng ng tip theo ca B l D cn dng 200g dung
dch NaOH nng
6u
31
%. Xc nh B v D, tnh t l s mol ca B v C trong hn
hp.
Gii
Phn tch Cht A ch cha 1 nguyn t Oxy, khi cho kh CO2 vo th thu c mt
dn xut ca benzenTrong A cng ch cha 1 nguyn t Na Cht A l dy
ng ng ca phenol, hoc ru thm.
Mt khc dy ng ng ca B c th tc dng c vi NaOH B v D khng
phi h ru thm B, D la dy ng ng ca phenol
CTPT ca A c dng CnH2n-7ONa (n 6) xc nh CTPT ca A thng qua phn
ng t chy:
p dng nh lut bo ton nguyn t Na ta c: nNa =2*
2,65
106
=0,0125 mol
nNa =nA =0,05mol MA =
5,8
0,05
=464 14n + 32 =116 n = 6
CTPT ca A l C6H5ONa CTPT ca B l C6H5OH (phenol) D l C7H7OH
Gi x, y ln lt l s mol ca B v D a = 94x + 108y (1)
Phn ng trung a gam hn hp B v D ta c:
x +y =
6a
31
200
10040
x + y =
3(94x+108)
310
y = 2x.
T l nB : nD =1:2.
Bi 2 Cho cht B tc dng vi hn hp HNO3 c, d v H2SO4 c thu c cht
T cho 18,32 gam T vo mt bnh chu p sut dung tch khng i 560cm
3
, v lm
n cht T nhit 1911
0
C. Tnh p sut trong bnh ti nhit , bit rng sn
phm n l hn hp CO, CO2, N2, H2 v p sut thc t nh hn p sut l thuyt
10%. [Tip theo bi 1]

122
Gii
Phn tch Dng bi ton ny lin quan n cc nh lut kh (ch xt kh l
tng). Do vy chng ta s n li nhng cng thc ca phng trnh kh l
tng:
Phng trnh kh l tng :
pV =nRT Vi:
n:s mol cht kh

p:p sut ca cht kh trong bnh
V:Th tch ca cht kh,th tch bnh
T:Nhit
R:Hng s ca cht kh R=0,082l.atm=8,314 J

iu kin nhit khng i ta lun c:
p
1
V
1
p
2
V
2
=
n
1
n
2

iu kin p sut khng i ta lun c:

;
iu kin th tch khng i:

Mt s trng hp c bit:
p sut v th tch khng i:

p sut v nhit khng i:

Th tch v nhit khng i:

n
1
T
1
n
2
T
2
=
V
1
V
2

p
1
T
1
p
2
T
2
=
n
1
n
2

n
1
n
2
=
T
2
T
1

V
1
V
2
=
n
1
n
2

p
1
p
2
=
n
1
n
2


123
Phng trnh phn ng ca phenol vi HNO3:

Cht T chnh l acid picric: nT =
18,32
229
=0,08 mol
Phn ng n:
2C6H3O7N3
t
0
2CO2 +3N2 +10CO +3H2
Tng s mol trong bnh:
nb =
(3+2+10+3)0,08
2
=0,72 mol
p dng phng trnh kh l tng: pV =nRT
p =
nR1
v
=
0,0720,082(273+1911)
2730,56
=2304 atm
p sut thc t trong bnh:
pthc =
90
100
*2304 =2073,6 atm.
Bi 3 A c CTPT ca C7H8O2 c vng benzen, bit:
0,1 mol A tc dng vi Na to thnh 0,1 mol H2
12,4 gam A tc dng va vi 4g NaOH
A phn ng vi dung dch Br2 theo t l 1:3. Xc nh CTCT ca A.
Gii
Phn tch p dng cng thc nh phn phng php gii ta d dng suy ra c s
nhm OH gn trn vng, v nhm OH gn trn dy.
Gi CTPT A c dng tng qut l: R(OH)m+n n = m = 1.

124
BI 11 ALDEHYDE R(CHO)n CETON (n 1).
A. KIN THC C BN
I. C CU DANH PHP
1. C cu
Aldehyd v Ceton l tn chung ca ca hai nhm hp cht cha nhm nh
chc Carbonyl C=O trong phn t. Aldehyd v Ceton khc nhau l do Aldehyd
cn hydrogen ni vi Carbon ca nhm Carbonyl. Cc nhm th ca Aldehyd
v Ceton rt t do c th l chi phng, chi hon, hng phng, bo ha, bt
bo ha. Vi Ceton, hai nhm th c th ging nhau (Ceton i xng), c th
khc nhau (Ceton bt i xng).

phn ng ca ni i C=O chu nh hng rt ln vo s phn cc ca ni
ny.
2. Danh Php
a. Danh php Aldehyd.
Tn dn xut acid
Loi tn ny c dn xut t thng thng ca acid, thay tip v ng ic hoc
oic trong tn ca acid bng Aldehyd.

Tn h thng
- Theo h thng IUPAC, dy chnh l dy cha mch Carbon di nht, c cha
nhm nh chc CHO. Thm tip ng -al vo sau tn hydrocarbon tng ng
vi dy chnh, carbon ca CHO nh s 1. Vi hp cht c cha hai nhm
chc CHO c th dng tip v ng dial. Vi hp cht c mang nhm nh
chc u tin hn Aldehyd, nhm th -CHO cn gi l nhm th formyl.

H
3
C
H
2
C
H
C
H
2
C CHO
CH
3
1
2
3
4
5
3-Metylpentanal

125
b. Ceton
Vit tn theo hai nhm th trc Ceton theo th t mu t.

Tn theo h thng
Chn dy chnh c cha mch Carbon di nht, thm tip ng -on sau tn
hydrocarbon tng ng vi dy chnh. nh s dy chnh sao cho Carbon c
cha nhm nh chc C=O mang s nh nht.

II. L TNH
S phn cc ca nhm carbonyl lm cho aldehyd v ceton l nhng cht hu
cc, do chng thng c im si cao hn cc hp cht c phn t tng
ng. Nhng v khng to c ni hydrogen lin phn t nn im si ca
aldehyd, ceton vn lun lun thp hn alcol v acid tng ng. Th d: im
si (
0
C) ca n-butylaldehyd (76), etylmetylceton (80), n-pentan (36),
dietyleter (35), alcol n-butyl (118), acid propinoic (141
0
C). Cc Aldehyd v
ceton cao hn tan tt trong dung mi hu c.
III. HA TNH
1. Phn ng do nhm carbonyl.
a. Cng nc
Phn ng ny cn c gi l s thy ha (Hydration), Aldehyd v ceton tc
dng vi nc cho ra 1,1 diol hay cn gi l gem-diol (geminal). Phn ng
thy ha l mt phn ng thun nghch. V tr cn bng ty thuc vo c cu
ca hp cht carbonyl, c cu cng t chng ngi th s to thnh gem-diol
cng c u i.
S cng nc ca aldehyd v ceton phn ng din ra rt chm, tc phn
ng ph thuc rt ln vo cht xc tc: acid, baz v iu kin nhit .


126
H
3
C
C
CH
3
O
+ H
2
O
H
3
C
C
OH
OH
CH
3
Aceton
Hydrat Ceton
99,9%
0,1%

b. Cng Alcol
Aldehyd v ceton phn ng thun nghch vi hai mol alcol xc tc acid cho ra
acetal v cetal.
V d:

c. Cng bisulfit NaHSO3
Khi cho Aldehyd hoc metylceton tc dng vi dung dch natrium bisulfit
(NaHSO3) bo ha ngi ta thu c cht rn khng ha tan trong lng tha
dung dch Bisulfit. Cht rn c gi l hp cht cng bisulfit.
Vi Aldehyd
R
C
H
O
+ : SO
2
-
Na
+
OH
RCHOH
SO
2
O
-
Na
+

Phn ng cng bisulfit din ra theo chiu thun
nghch, do cng dng chnh ca phn ng ny
l dng c lp cc hp cht ca nhm carbonyl,
trong hn hp vi vi cc hp cht hu c khc.


127
d. Cng Amoniac.
Amoniac cho phn ng cng d dng vi vi hu ht cc aldehyd. Sn phm
cng ny thng khng bn, kh nc cho hp cht bt bo ha cn gi l
aldimin.
R
C
H
O
+ NH
3
C
O
-
H
NH
3
+
R
R
H
C OH
NH
2
R C
H
NH +H
2
O
Aldimin

C ch cng Amin nht, nh cng cho sn phm tng t nh amoniac, i vi
ceton khng cho phn ng ny.
e. Cng tc cht Grignard
Aldehyd v ceton tc dng vi tc cht Grignard theo c ch phn ng cng
vo ni C=O cho ra alcol nh v alcol tam, tr trng hp formandehyd cho ra
alcol nht.
H
3
C C
H
3
C MgBr
O
H
H
3
C
H
C
OH
CH
3
+HOMgBr

2. Phn ng oxy ha
a. Phn ng oxy ha hon ton (Phn ng chy)
Aldehyd v Ceton chy cho ra CO2 v H2O, aldehyd v ceton no t chy cho s
mol CO2 v H2O nh nhau.
CnH2nO +
3n
2
O2 nCO2 + nH2O

Nhn xt

n
CO
2
=n
H
2
O


128
b. Phn ng trng bc
Phn ng trng bc ca aldehyd vi dung dch AgNO3 trong dung dch NH3
cho ra kt ta mu trng bc.
RCHO + 2AgNO3 +3NH3 +H2O RCOONH4 + 2Ag + 2NH4NO3
Phn ng c vit di dng thu gn nh sau:
RCHO + Ag2O RCOOH + 2Ag
Nhn xt: i vi dy ng ng ca fomandehyd tham gia phn ng trng
bc lun c:

o Vi aldehyd fomic HCHO tham gia phn ng trng bc xy ra theo hai
ln.
HCHO +4AgNO3 + NH3 +H2O
t
0
(NH4 )2CO3 +4Ag + 4NH4NO3
NH4)2CO3
t
0
NH3 + CO2
Nhn xt: Aldehyd fomic tham gia phn ng trn bc lun c:

Hai kh thot ra l kh CO2 v NH3
c. Phn ng vi Cu(OH)2
Phn ng ca Aldehyd vi dung dch Cu(OH)2 (mu xanh) cho kt ta mu
gch trong dung dch NaOH.
RCHO + 2Cu(OH)2 + 2NaOH RCOONa + Cu2O + 3 H2O
Nhn xt: Phn ng ny dng nhn bit
aldehyd vi cc nhm chc hu c khc.

Cu2O
3. Phn ng hon nguyn
a. Phn ng hon nguyn thnh alcol
Aldehyd hon nguyn thnh alcol I cn ceton thnh alcol II di s hydrogen
ha xc tc hoc vi nhng tc cht hon nguyn ha hc nh LiAlH4, NaBH4.
naldehyd = 2nAg
nfomic = 4nAg

129
V d:
b. Hon nguyn thnh hydrocarbon
C hai phng php chuyn ha nhm Carbonyl thnh nhm metylen c th
la chn s dng ty vo cht nn Carbonyl bn trong mi trng acid hay
baz. l phng php Clemmensen (dng Zn-Hg, HCl m c), v phng
php Wolff-Kishner (un Hydrazin v KOH trong alcol c im si cao khong
240
0
C).
V d:

4. Phn ng Halogen ha hydrogen

Chuyen de Hoa Huu Co

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Chuyen de Hoa Huu Co

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MT S CHUYN HA HC HA HC HU C

=1,9625*16 =31,4g/ mol

=1,2 iu ny chng t rng Y l mt acid carboxylic cha no.

n:s mol cht kh

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