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DN XUT HALOGEN ANCOL PHENOL

PHN 1: TM TT L THUYT
A. DN XUT HALOGEN
I. nh ngha, phn loi, ng phn v danh php.
1. nh ngha
Khi thay th mt hay nhiu nguyn t hiro trong phn t hirocacbon bng cc nguyn
t halogen ta c dn xut halogen ca hirocacbon, thng gi tt l dn xut halogen.
2. Phn loi : Dn xut halogen c dng C aHbXc ( X l halogen cn c l s nguyn t
halogen X)

Dn xut halogen no : CnH2n+1X


VD: CH3Cl, C2H5Br,

Dn xut halogen khng no: CnH2n-1X


VD: CH2= CH- Br,

Dn xut halogen thm : CnH2n-7X


VD: C6H5Br, C6H5Cl,

Bc halogen bng bc ca cacbon lin kt vi nguyn t halogen


3. Tn gi
Tn gc-chc: Tn gc hidrocacbon + halogennua
VD:
Tn thay th: S ch v trhalogen + tn hidrocacbon mch chnh
VD:
Tn thng thng:
VD:
II.Tnh cht ho hc.
1. Phn ng th nguyn t halogen bng nhm - OH
RX +

NaOH

C2H5 Br + NaOH

R OH + NaX

t C2H5
0

OH + NaBr

2. Phn ng tch hiro halogenua.


CH3 CH2 Br + KOH C H OH ,t CH2 = CH2 + KBr + H2O
2

Mt s ch :
ROH s h bin thnh cht khc khi OH gn vo C c cha ni i ci ny em s
c nhc n k hn trong mt s bi tp lin quan.
Khi nh s v c tn phi u tin lin kt i, ba ri mi n halogen, nh s sao
cho tng s ch v tr nhnh l nh nht.

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B. ANCOL V ETE
I. nh ngha, phn loi:
1. nh ngha:
Ancol l nhng HCHC trong phn t c nhm hiroxyl (- OH) lin kt trc tip vi nguyn
t cacbon no.
V d: CH3OH ; CH2 = CH CH2 OH ...
2 . Phn loi:
Ancol no, n chc, mch h c CTPT l: CnH2n + 1OH hay CnH2n + 2O (vi n 1).
II. ng phn, danh php:
1. ng phn: T C3H8O mi c ng phn.
ng phn mch cacbon.
ng phn v tr nhm chc.
V d: C4H10O c 4 ng phn ancol.
2 . Danh php :
a) Tn thng thng: Tn gi= ancol + tn gc hirocacbon + ic.
V d: C2H5OH : ancol etylic

C6H5CH2OH : ancol benzylic

b) Tn thay th: Tn gi= tn hirocacbon tng ng mch chnh + ch s v tr nhm OH


+ ol
V d: CH3 CH2 CH2- OH: ancol propylic hay propan 1ol
CH3 CH (OH) CH2: ancol isopropylic hay propan 2 ol
III. Tnh cht vt l:
- Cc ancol c nhit si cao hn cc hicacbon c cng phn t khi hoc ng phn ete ca n
l do gia cc phn t ancol c lin kt hiro Anh hng n tan.

IV. Tnh cht ho hc:


1. Phn ng th nguyn t hiro ca nhm OH:
a) Tnh cht chung ca ancol:
Nu ancol n:

2R(OH)x + 2xNa 2R(ONa)x + xH2


2ROH + 2Na 2RONa + H2

b) Tnh cht c trng ca glixerol: 2C3H5 (OH)3 + Cu(OH)2 [C3H5 (OH)2O]2Cu + H2O
ng (II) glixerat mu xanh lam

Phn ng ny dng phn bit ancol n chc vi ancol a chc c 2 nhm OH cnh
nhau trong phn t.
2 . Phn ng th nhm OH:

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a) Phn ng vi axit v c:

C2H5OH + HBr

to

2 SO4 d
H140
C2H5OH + HOC2H5
o
C

b) Phn ng vi ancol:

C2H5Br + H2O
C2H5 - O - C2H5 + H2O

2 SO4 d
H170
H CH2 CH2 OH
o
C

3. Phn ng tch H2O:

CH2 = CH2 + H2O

4. Phn ng oxi ho:


a) Phn ng oxi ho hon ton:

CnH2n +2 +

3n
O2 nCO2 + (n +1)H2O
2

b) Phn ng oxi ho khng hon ton:


CuO ,t o

ancol bc
I
ancol bc III
V d:

anehit.

CuO ,t o

ancol bc II

CuO ,t o

xeton

kh b oxi ho.
to

CH3 CH2 OH + CuO

CH3 CH OH CH3 + CuO

CH3 CHO + Cu + H2O


to

CH3 CO CH3 + Cu + H2O

V. iu ch:
1. Phng php tng hp:
a) Etanol:

CH2 = CH2 + H2O CH3CH2OH

t etilen

b) Glixerol:

Glixerol cn c sn xut bng phng php thu phn cht bo.


2 . Phng php sinh ho: t tinh bt, ng ...

(C6H5OH)n

H 2O
t o , xt

C6H12O6

enzim

C2H5OH

Mt s ch quan trng:
ru

Vancol
.100
Vdd

(mancol =Vancol dancol )

Khi tch nc ru X thu c cht Y m c t khi d X/Y k .


k > 1 th Y l anken v tch nc 1700C v ru X l no n.
k < 1 th Y l ete v n ete n H2O

n(n 1)
ete khc nhau.
2

1
n Ancol khi un n ru khc nhau s cho
2

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Tch nc ancol theo quy tc Zai xp.


t chy ancol no: n ancol n H2O n CO2
C. PHENOL V ANCOL THM
I. nh ngha, phn loi:
nh ngha :
Phenol l nhng HCHC trong phn t c nhm OH lin kt trc tip vi nguyn t
cacbon ca vng benzen.

Ancol thm l nhng cht c nhm OH gn vo mch nhnh ca vng benzen. Ancol
thm khng phi l axit nn khng phn ng vi NaOH.
V d:
II. Tnh cht ho hc:
a) Phn ng th nguyn t hiro ca nhm OH:
C6H5OH + Na C6H5ONa +

Tc dng vi kim loi kim:

H2

Natri phenolat
C6H5OH + NaOH C6H5ONa + H2O

Tc dng vi baz:

Phenol c tnh axit, tnh axit ca phenol rt yu; dung dch phenol khng lm i mu
qu tm.
b) Phn ng th nguyn t hiro ca vng benzen:
OH

OH
Br

Br
+ 3HBr

+ 3Br2
Br
2,4,6- trinitro phenol
OH

OH
+ 3HNO3

H2SO4 ac

O2N

NO2
+ 3H2O
NO2

2,4,6-trinitro phenol (axit picric)


4. iu ch: theo 2 cch.

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Cch 1:
CH 3

CH 2 CH
H

1) O2

2) ddH
2 SO4

Cch 2:

Br2
Fe ,t o

NaOH
to

HCl

PHN 2: PHNG PHP GII CC BI TP


L thuyt
1.

C bao nhiu ru (ancol) bc 2, no, n chc, mch h l ng phn cu to ca nhau m phn t


ca chng c phn trm khi lng cacbon bng 68,18%?
A. 2.

2.

C. 4.

D. 5.

Cc ng phn ng vi cng thc phn t C 8H10O (u l dn xut ca benzen) c tnh cht: tch
nc thu c sn phm c th trng hp to polime, khng tc dng vi NaOH. S lng ng
phn ng vi cng thc phn t C8H10O, tha mn tnh cht trn l
A. 4.

3.

B. 3.

B. 1.

C. 3.

D. 2.

Dy gm cc cht u phn ng vi phenol l:


A. dung dch NaCl, dung dch NaOH, Na.
B. nc brom, anehit axetic, dung dch NaOH.
C. nc brom, anhirit axetic, dung dch NaOH.
D. nc brom, axit axetic, dung dch NaOH.

4.

X l ng phn ng vi CTPT l C 6H13Br. Bit khi un nng X vi dung dch kim/etanol th thu
c 3 anken (tnh c ng phn hnh hc) v cc anken cng nc (xc tc axit) thu c sn
phm chnh khng b oxi ha bi CuO. Tn gi ca X l:
A. 1-bromhexan.

B. 3-brom-3-metylpentan.

C. 2-bromhexan.

D. 2-brom-2,3-imetylbutan.

Tch nc
1.

2.

Khi tch nc t mt cht X c cng thc phn t C 4H10O to thnh 3 anken l ng phn ca nhau
(tnh c ng phn hnh hc). Cng thc cu to thu gn ca X l
A. (CH3)3COH.

B. CH3CH(CH3)CH2OH.

C. CH3OCH2CH2CH3.

D. CH3CH(OH)CH2CH3.

Khi thc hin phn ng tch nc i vi ru (ancol) X, ch thu c mt anken duy nht. Oxi
ho hon ton mt lng cht X thu c 5,6 lt CO 2 ( ktc) v 5,4 gam nc. C bao nhiu cng
thc cu to ph hp vi X?
A. 5.

3.

B. 4.

C. 3.

Chia mt lng hn hp hai ancol no, n chc thnh hai phn bng nhau:
- Phn 1 em t chy hon ton thu c 2,24 l CO 2 (ktc)

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D. 2.

- Phn 2 em tch nc hon ton thu c hn hp hai anken.


t chy hon ton hai anken thu c bao nhiu gam nc?
A. 1,2g.

B. 1,8g.

C. 2,4g.

D. 3,6g.

Phn ng th
1.

2.

Cho 18,0 g hn hp hai ancol gm mt ancol no n chc v mt ancol n chc c mt lin kt


i trong phn t c s mol bng nhau tc dng ht vi Na thu c 4,48 lt H 2 ktc. Xc nh
CTCT hai ancol.
A. CH3CH2OH v CH2=CH-CH2OH.

B. CH3CH2CH2OH v CH2=CH-CH2OH.

C. CH3OH v CH2=CH-CH2OH.

D. Phng n khc.

Cho 15,6 gam hn hp hai ancol (ru) n chc, k tip nhau trong dy ng ng tc dng ht
vi 9,2 gam Na, thu c 24,5 gam cht rn. Hai ancol l
A. CH3OH v C2H5OH.

B. C3H7OH v C4H9OH.

C. C2H5OH v C3H7OH.

D. C3H5OH v C4H7OH.

Phn ng oxi ha khng hon ton


1.

Cho m gam mt ancol (ru) no, n chc X qua bnh ng CuO (d), nung nng. Sau khi phn
ng hon ton, khi lng cht rn trong bnh gim 0,32 gam. Hn hp hi thu c c t khi i
vi hiro l 15,5. Gi tr ca m l
A. 0,92.

2.

4.

5.

C. 0,32.

D. 0,64.

Cho mt hn hp hi metanol v etanol i qua ng cha CuO nung nng, khng c khng kh. Cc
sn phm kh v hi sinh ra c dn i qua nhng bnh cha ring r H 2SO4 c v KOH. Sau th
nghim,thy ng ng CuO gim 80 gam, bnh ng H 2SO4 tng 54 gam. Khi lng etanol tham
gia phn ng l
A. 46 gam.

3.

B. 0,46.

B. 15,33 gam.

C. 23 gam.

D. 14,67 gam.

un mt ancol X vi hn hp (ly d) KBr v H 2SO4 c thu c 12,3 gam cht hu c Y. Hiu


sut phn ng t 60%. Cht Y cha 29,27% C, 5,69% H v 65,04% mt nguyn t khc. Hi ca
12,3 gam Y ni trn chim mt th tch bng th tch ca 2,8 gam nit trong cng iu kin. Bit
khi oxi ha ancol X bi CuO thu c mt anehit. Cng thc cu to thu gn ca X v Y l
A. CH3-CH2OH v CH3CH2Br.

B. CH3-CH2-CH2OH v CH3CH2CH2Br.

C. CH3-CH2-CH2OH v CH3-CHBr-CH3.

D. CH2=CH-CH2OH v CH2=CHCH2Br.

Hn hp X gm ancol metylic v 1 ancol no, n chc A, mch h. Cho 2,76 gam X tc dng vi
Na d thu c 0,672l hiro (ktc), mt khc oxi ha hon ton 2,76g X bng CuO (t o) thu c
hn hp anehit. Cho ton b lng anhit ny tc dng vi dung dch AgNO 3/NH3 d thu c
19,44g kt tA. Cng thc phn t ca A l:
A. CH3CH2OH.

B. CH3CH2CH2OH.

C. CH3CH(CH3)OH.

D. (CH3)2CHCH2OH.

Cho 3 cht hu c n chc c cng cng thc phn t C 3H8O tc dng vi CuO (t oC) thu c
hn hp sn phm. Cho hn hp sn phm tc dng vi AgNO 3/NH3 d thu c 21,6g Ag. Nu
un nng hn hp 3 cht trn vi H 2SO4 c nhit 140oC th thu c 34,5g hn hp 4 ete v
4,5 gam H2O. Thnh phn % khi lng ru bc 2 c trong hn hp l:
A. 61,53%.

B. 46,15%.

C. 30,77%.

Phn ng oxi ha hon ton

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D. 15,38%.

1.

2.

t chy hon ton 3,075g hn hp 2 ancol no, n chc v cho sn phm ln lt i qua bnh 1
ng H2SO4 c v bnh 2 ng KOH rn. Tnh khi lng cc bnh tng ln bit rng nu cho
lng ru trn tc dng vi Na d thy bay ra 0,672 lt H 2 ktc.
A. Bnh 1 tng 3,645g, bnh 2 tng 6,27g.

B. Bnh 1 tng 6,27g, bnh 2 tng 3,645g.

C. Bnh 1 tng 3,645g, bnh 2 tng 5,27g.

D. Bnh 1 tng 3,645g, bnh 2 tng 7,27g.

t chy 1 mol ancol no X mch h cn 56 lt O 2 (ktc). Cng thc cu to ca X l


A. C3H5(OH)3.

3.

B. C2H4(OH)2.

D. C2H5OH.

X l mt ancol no, mch h. t chy hon ton 0,05 mol X cn 5,6 gam oxi, thu c hi nc v
6,6 gam CO2. Cng thc ca X l
A. C2H4(OH)2.

4.

C. C3H6(OH)2.

B. C3H6(OH)2.

C. C3H5(OH)3.

D. C3H7OH.

t chy hon ton m gam hn hp ancol A v B thuc loi ancol no, n chc, k tip nhau trong
cng dy ng ng thu c 5,6 lt CO 2 (ktc) v 6,3 gam nc. Mt khc oxi ha hon ton hai
ancol A v B bng CuO (t0) th thu c mt anehit v mt xeton. A, B ln lt l:
A. CH3OH v C2H5OH.

B. CH3CH2CH2OH v CH3CH2CHOHCH3.

C. C2H5OH v CH3CH2CH2OH.

D. CH3CHOHCH3 v CH3CH2OH

Phn ng sinh ancol


1.

Cho 7,872 lt kh C2H4 o 27oC; 1 atm hp th nc c xc tc, hiu sut 80% thu c ru X.
Ho tan X vo nc thnh 245,3 ml dung dch Y. ru trong dung dch Y l:
A. 40.

2.

B. 120.

C. 60.

D. 80.

Cho hn hp hai anken ng ng k tip nhau tc dng vi nc (c H 2SO4 lm xc tc) thu c


hn hp Z gm hai ru (ancol) X v Y. t chy hon ton 1,06 gam hn hp Z sau hp th
ton b sn phm chy vo 2 lt dung dch NaOH 0,1M thu c dung dch T trong nng ca
NaOH bng 0,05M. Cng thc cu to thu gn ca X v Y l (Cho: H = 1; C = 12; O = 16; th tch
dung dch thay i khng ng k).
A. C2H5OH v C3H7OH.

B. C3H7OH v C4H9OH.

C. C2H5OH v C4H9OH.

D. C4H9OH v C5H11OH.

Phenol v ru thm
1.

Cho s
C6H6 (benzen)

+Cl2 (tlmol 1:1)


Fe, to

+NaOH

c (d )
to cao, p cao

+axit HCl

Hai cht hu c Y, Z ln lt l:

2.

3.

A. C6H6(OH)6 v C6H6Cl6.

B. C6H4(OH)2 v C6H4Cl2.

C. C6H5ONa v C6H5OH.

D. C6H5OH v C6H5Cl.

Khi t 0,1 mol cht X (dn xut ca benzen), khi lng CO 2 thu c nh hn 35,2 gam. Bit
rng 1 mol X ch tc dng c vi 1 mol NaOH. Cng thc cu to thu gn ca X l
A. HOCH2C6H4COOH.

B. C6H4(OH)2.

C. C2H5C6H4OH.

D. C6H4(CH3)OH.

Hp cht hu c X (phn t c vng benzen) c cng thc phn t l C 7H8O2, tc dng c vi


Na v vi NaOH. Bit rng khi cho X tc dng vi Na d, s mol H 2 thu c bng s mol X tham
gia phn ng v X ch tc dng c vi NaOH theo t l s mol 1:1. Cng thc cu to thu gn
ca X l

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A. C6H5CH(OH)2.
4.

B. HOC6H4CH2OH.

C. CH3C6H3(OH)2.

D. CH3OC6H4OH.

Mt hn hp X gm hai cht thuc dy ng ng phenol A v B hn nhau 1 nhm CH 2. t chy


ht X thu c 83,6g CO2 v 18g H2O. Tm tng s mol A, B v CTCT ca A, B.
A. 0,2 mol;C6H5OH v CH3C6H4OH.

B. 0,3 mol; C6H5OH v CH3C6H4OH

C. 0,2 mol;CH3C6H4OH v C2H5C6H4OH.

D. 0,3 mol; CH3C6H4OH v C2H5C6H4OH.

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