E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.

doc
1
DN XUT HALOGEN ANCOL PHENOL
A L THUYT
1 DN XUT HALOGEN
1.1. Khi nim
Khi thay th mt hay nhiu nguyn t hidro trong phn t hidro bng mt hay nhiu nguyn t
halogen ta c dn xut ca halogen ca hidrocacbon, thng gi l dn xut halogen.
R H R X (X =F, Cl, Br, I)
1.2. Phn loi
1.2.1. Theo bn cht ca nguyn t halogen X
- Dn xut flo, th d: CF
2
=CF
2
.
- Dn xut clo, th d: CH
3
Cl.
- Dn xut brom, th d: C
6
H
5
Br.
- Dn xut iot, th d: (CH
3
)
3
CI.
- Dn xut cha ng thi nhiu halogen, th d: CH
2
FCl.
1.2.2. Theo cu to gc hidrocacbon
- Dn xut halogen no, th d: C
2
H
5
Br.
- Dn xut halogen khng no, th d: CH
2
=CHCl.
- Dn xut halogen thm, th d: C
6
H
5
-CH
2
Cl.
Hoc c th phn theo mch C ca gc thnh 2 loi: Dn xut halogen mch h v dn xut
halogen mch vng.
1.2.3. Theo bc ca dn xut halogen
Bc ca dn xut halogen l bc ca nguyn t C lin kt vi nguyn t halogen. Th d:
CH
3
CH
2
CH
2
Cl
I
CH
3
CHCl CH
3
II
CH
3
CCl
CH
3
CH
3
III

Dn xut halogen bc I Dn xut halogen bc II Dn xut halogen bc III
1.3. ng phn
Dn xut halogen c ng phn mch C nh hidrocacbon, ngoi ra cn c ng phn v tr
nguyn t halogen (V tr nhm chc).
Th d, C
4
H
9
Cl:
CH
3
CH
2
CH
2
CH
2
Cl
CH
3
H
C
H
3
C
CH
2
Cl
CH
3
C
CH
3
CH
2
Cl
CH
3
CH
3
CH
2
CHCl CH
3
CH
3
Cl
C
CH
3
CH
3

1.4. Danh php
1.4.1. Danh php thng thng
Th d: CHCl
3
clorofom; CHBr
3
bromofom; CHI
3
iodofom;
1.4.2. Danh php gc chc
Tn dn xut = tn gc hidrocacbon + halogenua
Th d: CH
2
Cl
2
metylen clorua; CH
2
=CHCl Vinyl clorua
CH
2
=CH-CH
2
Cl Anlyl clorua; C
6
H
5
-CH
2
-Br benzyl bromua
1.4.3. Danh php thay th
Tn dn xut = s ch v tr X tn X + tn hidrocacbon
Th d: CH
3
CH
2
Cl clo etan; ClCH
2
-CH
2
Cl 1,2-iclo etan;


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
2
1.5. iu ch
1.5.1. Halogen ha hidrocacbon
* Phn ng th:
Th d: CH
4
+Cl
2

as
CH
3
Cl
+Br
2
Br
+HBr
as

CH
3
+Br
CH
3
Br
CH
3
Br
Fe
- HBr

CH
2
=CH-CH
3
+Cl
2

500 600
o
C
CH
2
=CH-CH
2
Cl
* Phn ng cng
Th d: - CH
2
=CH
2
+Br
2
CH
2
Br-CH
2
Br
- R-CH=CH
2
+HX R-CHX-CH
3

- HC=CH +HCl
2
150 200
o
HgCl
C
CH
2
=CHCl
1.5.2. Tng hp t ancol
R-OH +HX
2
o
ZnCl
t
R-X +H
2
O
Hoc: R-OH +PCl
5
RCl +POCl
3
+HCl
3R-OH +PI
3
3RI +H
3
PO
3

1.6. Tnh cht vt l
Cc dn xut halogen hu nh khng tan trong nc, tan tt trong cc dung mi khng phn
cc nh hidrocacbon, ete,
Nhit si ca dn xut halogen c cng gc hidrocacbon gim dn t dn xut iodua n
dn xut florua:
t
o
s
: R-I >R-Br >R-Cl >R-F
Vi cc ankyl halogen c thnh phn ging nhau, nhit si ca dn xut bc I ln hn nhit
si ca dn xut bc II, dn xut bc III c nhit si thp nht.
t
o
s
: Dx bc I >Dx bc II >Dx bc III
1.7. Tnh cht ha hc
Kh nng phn ng ca cc dn xut halogen thay i ty theo bn cht nguyn t halogen v
gim dn t iot n clo, ring dn xut flo c xp vo hp cht tr:
R I >R Br >R Cl
S thay i kh nng phn ng ca dn xut R-X hon ton ph hp vi gi tr nng lng lin
kt v s phn cc lin kt:
- Nng lng lin kt: C-Cl (75kcal) >C-Br (65kcal) >C-I (57kcal).
- phn cc lin kt: C I >C Br >C Cl.
Cu to gc R cng nh hng n kh nng v c ch phn ng ca dn xut halogen.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
3
1.7.1. Phn ng th nguyn t X bng nhm OH (phn ng thy phn)
R-X H
2
O H
2
O, t
o
Dd NaOH, t
o

Ankyl halogenua - - +(1)
Anlyl halogenua - +(2) +(1)
Phenyl halogenua - - - (3)
- (1): C
n
H
2n+1
-X +OH
-

o
t
C
n
H
2n+1
-OH +X


- (2): RCH=CHCH
2
X +H
2
O
o
t

RCH=CHCH
2
-OH +HX
- (3): Cc dn xut phenyl halogenua (X nh trc tip vo vng benzen) khng phn ng vi
dung dch kim nhit thng v ngay c khi un si. Chng ch phn ng nhit v p sut
cao. Th d:
C
6
H
5
-Cl +NaOH
300
200
o
C
atm
C
6
H
5
-ONa +NaCl +H
2
O
1.7.2. Phn ng tch
Phn ng tch HX c th xy ra vi cc dn xut c t nht 1H C

:
C C
H
X
+OH
-
C C
+HX

Th d: CH
3
CH
2
Br +KOH
o
t
ancol
CH
2
=CH
2
+KBr +H
2
O
* Hng ca phn ng tch - Quy tc tch Zaixep:
Khi tch HX khi dn xut halogen, nguyn t halogen u tin tch ra cng vi nguyn t H
nguyn t C

c bc cao hn (C

c t H hn ngho cng ngho).

Th d:
CH
3
CH =CH CH
2
(spc)
CH
3
CHBr CH
2
CH
3

CH
2
=CH CH
2
CH
3
(spp)
1.7.3. Phn ng vi kim loi to hp cht c kim
Cc dn xut clo, brom, iot c th phn ng vi Mg trong mi trng ete khan to thnh hp
cht c magie:
R X +Mg
etekhan
R MgX
Hp cht c magie rt d tham gia phn ng th vi nhng hp cht c H linh ng (nc,
ancol, NH
3
, phenol, amin, ank-1-in,):
R-MgX +HA RH +MgXA
Th d: R-MgBr +H
2
O RH +Mg(OH)Br
R-MgBr +CH
3
-C=CH RH +CH
3
-C=C-MgBr
1.7.4. Phn ng vi Na (Phn ng Wurt)
2RX +2Na R R +2NaX
C th s dng phn ng ny tng mch C trong qu trnh iu ch hidrocacbon.
1.7.5. Phn ng kh
R X
2H
Zn HCl

R- H+HX
Phn ng ny dng iu ch ankan c cng s C vi dn xut halogen.

- HBr

KOH, ancol, t
o


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
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2. ANCOL
2.1. nh ngha ancol iu kin ancol bn
2.1.1. nh ngha
Ancol l nhng hp cht hu c m phn t c nhm hydroxyl (-OH) lin kt trc tip vi
nguyn t C no.
2.1.2. iu kin ancol bn
- Nhm OH phi nh vi C no.
- Mi nguyn t C khng nh qu 1 nhm OH.
Nu mt trong hai iu kin trn b vi phm, ty theo tng tnh hung m c th xy ra cc
trng hp sau:
2.1.2.1. Khi nhmOH nh vi nguyn t C lin kt i
Khi nhm OH nh vi C lin kt i s t chuyn v thnh andehit hoc xeton ty thuc
vo v tr ca nguyn t C .
- Nu nhm OH nh vi nguyn t C ti lin kt i u mch th ancol s chuyn v thnh
andehit:
C CH OH
H
C CHO

- Nu nhm OH nh vi C ti lin kt i pha trong mch th ancol s chuyn v thnh
xeton:
C
C
OH
C
C CH
O
C

H qu: Ancol khng no phi c t nht 3 nguyn t C (n3)
2.1.2.2. Khi mt nguyn t C lin kt trc tip vi hn 1 nhm OH
- Nu c 2 nhm OH nh vo cng mt nguyn t C u mch th s tch nc to thnh
andehit:
H
C OH
OH
C
CHO C +H
2
O

- Nu c 2 nhm OH nh vo cng mt nguyn t C pha trong mch th s tch nc to thnh
xeton:
C C
OH
C
C C +H
2
O
OH
O
C

- Nu c 3 nhm OH cng nh vo mt nguyn t C th s tch nc to thnh axit:
C OH
OH
C
C C +H
2
O
OH
O
OH

H qu: 1- Nu trong phn t dn xut halogen c nhiu nguyn t X cng nh vo mt nguyn t
C khi tc dng vi dung dch kim s khng thu c ancol. Th d:
CH
3
CHCl
2
+2NaOH CH
3
CHO +2NaCl +H
2
O
CH
3
CBr
3
+3NaOH CH
3
COOH +3NaBr +H
2
O
CHBr
2
CHBr
2
+4NaOH (CHO)
2
+4NaBr +2H
2
O
2- S nguyn t O trong phn t ancol lun lun nh hn hoc bng s nguyn t C. Nh
vy, nu gi cng thc ca ancol l C
x
H
y
(OH)
a
th iu kin l: _ a x.



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
5
2.2. Cng thc tng qut
2.2.1. Theo thnh phn nguyn t: C
n
H
2n+2-2k
O
a

Trong :
- n: S nguyn t C c trong phn t, n 1.
- k: S lin kt +s vng; 0 k n vi n chn v 0 k n-1 vi n l.
- a: S nguyn t O v cng chnh l s nhm chc OH, 1 a n.
T cng thc tng qut trn ta c th thy cng thc tng qut ca ancol chnh l cng thc
ca hidrocacbon +a nguyn t O (a: s nhm chc ancol). Do , s nguyn t H trong ancol lun
l s chn.
Hoc: C
x
H
y
O
z
vi: 1 a x, y 2x+2, y chn.
2.2.2. Theo dng gc - chc: R(OH)
a
hoc C
n
H
2n+2-2k-a
(OH)
a

Hoc C
x
H
y
(OH)
a
vi: 1 a x, y+a 2x + 2, y + a chn.
Ch : Ty theo c im ca bi ton m ta gi cng thc tng qut ca ancol theo mt trong cc
dng trn:
- Nu cho dng t chy th nn vit CTPT ancol di dng thnh phn nguyn t.
- Nu cho dng phn ng phn chc th nn vit CTPT ancol theo dng gc chc.
- Nu cho php xc nh khi lng mol phn t ancol th vit CTPT ancol di dng tng
qut R(OH)
a
.
2.3. Phn loi
2.3.1. Theo s lng nhm chc (s lng nhm -OH): 2 loi
2.3.1.1. Ancol n chc (ru 1 ln ru): Ancol m trong phn t ch cha mt nhmOH.
CTTQ: C
n
H
2n+2-2k
O
Hay: C
n
H
2n+1-2k
OH
Hay: R-OH
Ancol n chc c phn t lng nh nht: CH
3
OH (M=32).
2.3.1.2. Ancol a chc: Ancol m phn t c cha t 2 nhmOH tr ln.
CTTQ: C
n
H
2n+2-2k-a
(OH)
a

Hay: C
n
H
2n+2-2k
O
a
(2an)
Hay: R(OH)
a

- Ancol hai chc (ru 2 ln ru): C
n
H
2n-2k
(OH)
2
, C
n
H
2n+2-2k
O
2
, R(OH)
2

- Cc ancol a chc tiu biu:
+C
2
H
6
O
2
, hay C
2
H
4
(OH)
2
, hay CH
2
(OH) CH
2
(OH): etylenglycol
+C
3
H
8
O
3
, hay C
3
H
5
(OH)
3,
hay CH
2
(OH)CH(OH)CH
2
(OH): glixerin, glixerol.
Ch : 1 - Cc ancol metylic, etylenglycol v glyxerol c khi lng mol phn t lp thnh mt
cp s cng c cng sai d =30.
2 - Khi lng phn t ca ancol a chc nh nht l 62 (C
2
H
4
(OH)
2
), nn khi lng phn
t ca cc ancol a chc M 62 v mt ancol c M <62 th phi l ancol n chc.
3 - Khi lng phn t ca ancol 3 chc nh nht l 92 (C
3
H
5
(OH)
3
) nn nu ancol c
M<92 th ancol ch c th l ancol n chc hoc hai chc.
Th d: T khi hi ca mt ancol so vi H
2
bng 29. Tm CTPT v vit CTCT ca ancol.
Gii
M =29.2=58 <62 nn ancol l ancol n chc ROH.
R =58 -17 =41 (C
3
H
5
)
Vy CTPT ca ancol l C
3
H
5
OH. CTCT: CH
2
=CH-CH
2
-OH


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
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2.3.2. Theo gc hidrocacbon: 3 loi
2.3.2.1. Ancol no: Ancol c gc hidrocacbon l gc no.
Ch : Theo nh ngha ancol no c th l mch h hoc mch vng. Tuy nhin, theo thi quen khi
dng thut ng ancol no thng c hiu km l mch h; nhng mt s bi ton li chnh
dng s thng ny ci by. Nn gp bi ton ny, nu thy khng hp l (tha d kin hay
khng c nghim) th phi thay vic coi l ancol no, mch h thnh gi CTPT ancol l C
x
H
y
OH.
- Ancol no, n chc, mch h: C
n
H
2n+1
OH; C
n
H
2n+2
O (n1).
- Ancol no, hai chc, mch h: C
n
H
2n
(OH)
2
; C
n
H
2n+2
O
2
(n2).
2.3.2.2. Ancol khng no: Ancol c gc hidrocacbon l gc khng no.
- Ancol khng no, n chc, mch h mt lin kt i: C
n
H
2n
O; C
n
H
2n-1
(OH) (n3). Th d:
CH
2
=CH-CH
2
-OH (ancol anlylic)
- Ancol khng no, n chc, mch h mt lin kt ba: C
n
H
2n-2
O; C
n
H
2n-3
(OH) (n3). Th d:
CH=C-CH
2
-OH (pincol)
2.3.2.3. Ancol thm: Ancol c gc hidrocacbon l gc thm, nhng nhm OH khng nh vo
nguyn t C ca vng benzen.
Th d: C
6
H
5
-CH
2
-OH (ancol benzylic). Ancol thm phi c t nht 7C trong phn t.
Ancol thm, n chc, 1 vng benzen: C
6
H
5
-C
n
H
2n-2k
-OH (1n)
2.3.3. Theo bc ca nguyn t C m nhm OH nh vo: 3 loi
Bc ca ancol l bc ca nguyn t C m nhm OH nh vo. Bc ca C c tnh bng s
lin kt m nguyn t C lin kt trc tip vi cc nguyn t C khc.
Ch : 1 Ancol CH
3
OH mc d c C bc 0 nhng vn c coi l ancol bc I.
2 Ancol bc II phi c t nht 3C; ancol bc III phi c t nht 4C.
CH
3
CH
2
OH CH
3
H
C CH
3
OH
CH
3
C CH
3
OH
OH
I II III

Ancol bc I Ancol bc II Ancol bc III
2.3.3.1. Ancol bc I: L ancol trong nhm OH nh vo nguyn t C bc I.
c im: ancol bc I c nhm -CH
2
OH, nh vy mi nhm chc OH s ch c 1 C

(Nguyn
t C gn trc tip vi CH
2
OH).
CTTQ: R-(CH
2
OH)
a
hay C
n
H
2n+2-2k-a
(CH
2
OH)
a
.
+ Ancol n chc bc I: R-CH
2
OH hay C
n
H
2n+2-2k
CH
2
OH.
+ Ancol no, n chc mch h: C
n
H
2n+1
CH
2
OH.
2.3.3.2. Ancol bc II: L ancol trong nhm OH nh vo nguyn t C bc II.
c im: Trong phn t c nhm CH(OH), do ng vi mi nhm chc s c 2 C

.
- Ancol bc II i xng (2 C

hon ton ging nhau):

CH
3
CH
CH
3
OH
CH
2
CH
CH
2
OH
CH
3
CH
3

- Ancol bc II khng i xng:
CH
3
CH
CH
3
OH
CH
2
CH
CH
OH
CH
3
CH
3
CH
2
CH
3

2.3.3.3. Ancol bc III: l ancol trong nhm -OH nh vo nguyn t C bc III.
c im: Trong phn t c nhm C(OH), nn ng vi mi nhm chc c 3 C

.
- Ancol bc III c 3 C

hon ton ging nhau:

E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
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CH
3
C
CH
3
OH
CH
2
C
CH
2
OH
CH
3
CH
3
CH
3
C
2
H
5

- Ancol bc III c 2 C

ging nhau:
CH
3
CH
3
C
CH
3
OH
CH
2

- Ancol bc III khng c C

no ging nhau:
CH
3
CH
2
C
CH
OH
CH
3 CH
3
CH
3

2.4. Danh php
2.4.1. Danh php thng thng:
Tn ancol R-OH = Ancol + tn gc R + ic
2.4.2. Danh php thay th:
Tn ancol = Tn hidrocacbon tng ng mch chnh + s ch v tr ol
2.4.3. Th d:
2.4.3.1. Ancol no, n chc, mch h: Ankanol
Ancol Ancol ankylic Ankanol
CH
3
OH Ancol metylic Metanol
C
2
H
5
OH Ancol etylic Etanol
CH
3
CH
2
CH
2
OH Ancol n-propylic Propan-1-ol
CH
3
CH(OH)CH
3
Ancol iso-propylic Propan-2-ol
CH
3
CH
2
CH
2
CH
2
OH Ancol n-butylic Butan-1-ol
CH
3
CH(OH)CH
2
CH
3
Ancol sec-butylic Butan-2-ol
CH
3
CH(CH
3
)CH
2
OH Ancol iso-butylic 2-metyl-propan-1-ol
(CH
3
)
3
COH Ancol tec-butylic 2-metyl-propan-2-ol
CH
3
(CH
2
)
3
CH
2
OH Ancol amylic Pentan-1-ol
(CH
3
)
2
CHCH
2
CH
2
OH Ancol iso-amylic 3-metyl-butan-1-ol
2.4.3.2. Ancol khng no v ancol thm
Ancol Dp thng thng Dp thay th
CH
2
=CH-CH
2
-OH Ancol anlylic Propenol
CH=C-CH
2
-OH Ancol pincol Propinol
C
6
H
5
-CH
2
-OH Ancol benzylic Phenyl metanol
2.4.3.3. Ancol a chc
Ancol Dp thng thng Dp thay th
C
2
H
4
(OH)
2
Etylen glycol Etan-1,2-diol
C
3
H
5
(OH)
3
Glyxerol (glyxerin) Propan-1,2,3-triol


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
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2.5. Tnh cht vt l
Tt c cc ancol u nh hn nc.
2.5.1. Ancol n chc
2.5.1.1. Trng thi
iu kin thng, cc ankanol t CH
3
OH n C
12
H
25
OH l cht lng, t C
13
H
27
OH tr ln l
cht rn.
Cc ankanol u dy l nhng cht khng mu.
2.5.1.2. Tnh tan
Cc ancol t C
1
n C
3
tan v hn trong nc, khi s nguyn t C tng ln th tan gim dn.
Gii thch: Cc ancol tan c trong nc do c nhm OH to lin kt hidro vi phn t
H
2
O. Khi mch C tng, tnh k nc ca gc hidro tng nn tnh tan gim xung.
ru: L i lng biu th s phn th tch ca ancol trong 100 phn th tch dung dch
ancol trong nc.
V
o ancol
( )= .100
V
dd

Th d: Ancol 30
0
l dung dch c 30ml ancol trong 100ml dung dch.
Cc ancol cn c th ha tan c nhiu cht hu c, do ancol c s dng kh nhiu lm
dung mi.
2.5.1.3. Nhit si
Nhit si ca cc ancol cao hn nhiu so vi ete, andehit, hidrocacbon, c khi lng
tng ng, do s to thnh lin kt hidro gia cc phn t.
Trong cng dy ng ng, nhit si ca cc ancol tng theo chiu tng khi lng phn t.
Cc ancol ng phn, nhit si ca cc ancol bc I cao hn nhit si ca cc ancol bc
cao hn. C th do ancol bc I th lin kt O-H phn cc hn cc ancol bc cao nn lin kt hidro
gia cc phn t ancol bc I mnh hn lin kt hidro gia cc phn t ca cc ancol bc cao. V
cc ng phn mch thng c nhit si cao hn cc ng phn mch nhnh.
2.5.2. Ancol a chc
Cc poliol nh etylen glycol, glyxerol l nhng cht lng trong sut, thng snh, nng hn
nc, tan nhiu trong nc, ho nc v c v ngt. Chng c s dng lm cht gi m trong sn
xut kem, sp chng n, mc bt bi; pha vo thc phm tng snh.
Cc ankandiol c nhit ng c thp nn c s dng lm cht chng ng.
2.6. Tnh cht ha hc
2.6.1. c im cu to
Trong nhm OH, nguyn t O c m in ln ( 3,44 2,20
O H
c c = = ) nn ht e mnh,
lm cho 2 lin kt O H v C O phn cc v pha O nn km bn, d b t trong qu trnh tham
gia phn ng ha hc.
- tc dng vi kim loi kim H
2

- oxi ha khng hon ton andehit, xeton, axit,
- tc dng vi axit c oxi este

- t 1 phn t ankanol anken
- t 2 phn t ancol ete
- tc dng vi axit khng c oxi este

(2)
(1)
H
C O


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
9
2.6.1.1. Phn ng lin kt O H
Lin kt O H cng km phn cc, phn ng ct t lin kt O H xy ra cng kh khn.
- Vi cc ancol n chc, gc ankyl R c tc dng y e (+I) lm s phn cc ca lin kt O H
gim, do cc ankanol n chc c tnh axit ( linh ng ca nguyn t H nhm OH) nh hn
H
2
O v RO c tnh baz ln hn OH. V ankanol bc III <ankanol bc II <ankanol bc I.
- Vi cc ankanpoliol c cc nhm OH nh 2 C k cn, do nh hng ht e ca nhm OH (-
I) ny so vi nhm kia lm cho lin kt O H nhm OH tr ln linh ng hn so vi ankanol n
chc, v vy cc ankanol ny d tham gia phn ng este ha hn so vi ankanol n chc. Tuy
nhin, tnh axit ca chng vn nh hn ca H
2
O. Vi cc ankanpoliol c cc nhm OH cch xa
nhau, nh hng qua li gia cc nhm OH l khng ng k nn chng ging cc ankanol n
chc.
- Nu gc R c cc nhm ht e (-I, -C) th phn cc ca lin kt OH s tng ln.
2.6.1.2. Phn ng lin kt C O
Lin kt CO cng phn cc th cng km bn, d b ct t tham gia cc phn ng kh
H
2
O.
2.6.1.3. Phn ng gc R
Ngoi hai trung tm phn ng k trn, cc ancol cn c cc phn ng gc R. Nh: phn ng
cng, trng hp, nu R khng no; phn ng th nu R no; phn ng cng, th nhn nu l
ancol thm.
2.6.2. Tnh cht ha hc
2.6.2.1. Phn ng vi kimloi kim ancolat + H
2

a) Bn cht phn ng l phn ng th:
-OH +M -OM + H
2
(M =K, Na,)
b) Do phn ng ch xy ra nhmchc nn khi vit phng trnh ha hc nn vit CTPT ca
ancol dng gc chc.
R(OH)
a
+a M R(OM)
a
+
2
a
H
2

Ch : Khi cho dung dch ancol trong nc phn ng vi kim loi kim th trc tin c phn ng
ca kim loi kim vi nc sau mi n phn ng ca kim loi kim vi ancol.
M +H
2
O MOH + H
2

c) Sn phmphn ng:
* Sn phmrn (khi c cn): mui ancolat l cht rn, mu trng kh bay hi. V tnh axit ca cc
ancolat nh hn H
2
O nn cc ancolat b thy phn trong nc, th d ancolat natri:
R(ONa)
a
+aH
2
O R(OH)
a
+aNaOH
Dung dch ancolat c tnh baz, chng lm i mu qu tm sang mu xanh. Li dng phn
ng gia ancol v kim loi kim to thnh ancolat kh bay hi v phn ng thy phn ancolat
ngi ta c th tch ancol ra khi hn hp hoc lm khan ancol. Phn ng thy phn ancolat cng
chnh l phn ng chng minh tnh axit ca ancol nh hn ca nc.
* Sn phmkh: Theo s phn ng, c mi nhm OH phn ng s gii phng ra mt nguyn t
H v cn mt nguyn t kim loi kim M. Do , khi bit t l s mol H
2
v s mol ancol phn ng
(hoc t l s mol ancol vi s mol kim loi phn ng) ta s xc nh c s nhm chc ca ancol:
2
H M p
ancol p ancol p
n n
a
= ; Hay: =a
n 2 n

- Nu mt ancol phn ng cho =
2
H ancol p
1
n n
2
th ancol l ancol n chc.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
10
- Nu hn hp cc ancol phn ng vi kim loi kim cho =
_
2
H ancol p
1
n n
2
th hn hp cc
ancol l hn hp cc ancol n chc.
- Mt ancol tc dng vi kim loi kim cho _
2
H ancol p
n n th l ancol a chc. V nu l iol
th
2
ancol H
n =n .
- Nu hn hp cc ancol phn ng vi kim loi kim cho <
_
2
H ancol p
n n th hn hp ancol
c t nht mt ancol n chc. Ngc li, nu cho
1
2

_
2
H ancol p
n n th hn hp ancol c t
nht mt ancol a chc.
- Tng t ta c th bin lun s nhm chc theo t l s mol kim loi kim vi s mol ancol:
Nu
M p
ancol p
n
=1
n
th l anol n chc, cn nu 2 _
M p
ancol p
n
n
th l ancol a chc.
Nu
_
M p
hh ancol p
n
=1
n
th hn hp l hn hp cc ancol n chc.
Nu
_
M p
hh ancol p
n
>1
n
th hn hp c t nht 1 ancol a chc.
Nu
_
M p
hh ancol p
n
<2
n
th hn hp c t nht 1 ancol n chc.
2.6.2.2. Phn ng este ha
Phn ng este ha l phn ng gia ancol vi axit hu c hoc v c, sn phm phn ng l
este hu c hoc este v c.
a) Phn ng to estev c
R(OH)
a
+aHX
o
2 4c
H SO , t
RX
a
+aH
2
O
Th d: C
2
H
5
OH +HBr
o
2 4c
H SO , t
C
2
H
5
Br +H
2
O
Ch : 1- Nu ancol l ancol khng no th cn c phn ng cng vo gc hidrocacbon:
CH
2
=CH-CH
2
OH +2HCl
o
2 4c
H SO , t
CH
3
-CHCl-CH
2
Cl +H
2
O
2- Nu axit c c l HI th cn c th xy ra phn ng kh ankanol thnh ankan:
C
2
H
5
OH +2HI
o
Photpho, t
C
2
H
6
+I
2
+H
2
O
3- Trong phn ng vi axit v c, nhm OH ca ancol b tch ra. Do vy khi vit phng
trnh ha hc ca phn ng cng nn vit cng thc phn t ancol dng gc chc nh trn.
b) Phn ng to este hu c
Ancol phn ng vi axit cacboxylic v dn xut nh clorua axit, anhidrit axit to este hu c:
- COOH +HO-
o
2 4c
H SO , t

-COO- +H
2
O
phn ng ny, phn t H
2
O c to ra t nhm OH ca axit v nguyn t H ca ancol. V
phn ng cng ch xy ra nhm chc nn khi vit cc phng trnh ha hc ca phn ng ta vit
cng thc phn t ancol dng gc chc.
* Phn ng ca ancol n chc vi axit n chc este n chc:
RCOOH +ROH
o
2 4c
H SO , t

RCOOR +H
2
O




E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
11
- 1 ancol n chc +hn hp axit n chc hn hp cc este n chc cng gc ancol:
o
2 4c
H SO , t
2
RCOOH+R'OH RCOOR'+H O

- Hn hp cc ancol n chc + 1 axit n chc hn hp cc este n chc cng gc axit:
o
2 4c
H SO , t
2
RCOOH+R'OH RCOOR'+H O

- Hn hp cc ancol n chc +hn hp cc axit n chc hn hp cc este n chc:
o
2 4c
H SO , t
2
RCOOH+R'OH RCOOR'+H O

- Hp cht tp chc cha 1 nhm OH v 1 nhm COOH c th t phn ng to ra este vng,
hoc trng ngng to ra polime:
OH CH
2
CH
2
COOH
H
2
C
H
2
C
C
H
2
CH
2
C
O
O
+H
2
O

OH CH
2
CH
2
COOH
+nH
2
O
O CH
2
CH
2
C
O
n
n

* Phn ng ca ancol n chc vi axit cacboxylic a chc:
Nu sn phm sau phn ng vn c kh nng phn ng vi NaOH hoc Na
2
CO
3
chng t vn
cn COOH cha tham gia phn ng este ha. Nu tt c cc nhm COOH este ha s thu c
s chc este bng s chc axit ca axit caboxylic:
R(COOH)
a
+aROH
o
2 4c
H SO , t

R(COOR)
a
+aH
2
O
Th d:
HOOC-COOH +CH
3
OH
o
2 4c
H SO , t

HOOC-COOCH
3
+H
2
O
HOOC-COOH +2CH
3
OH
o
2 4c
H SO , t

CH
3
OOC-COOCH
3
+2H
2
O
- C
3
H
5
(COOH)
3
+ROH:
CH
2
COOH
CHCOOH
CH
2
COOH
+ROH
CH
2
COOR
CHCOOH
CH
2
COOH
CH
2
COOH
CHCOOR
CH
2
COOH
CH
2
COOR
CHCOOR
CH
2
COOH
CH
2
COOR
CHCOOH
CH
2
COOR
CH
2
COOR
CHCOOR
CH
2
COOR

- C
3
H
5
(COOH)
3
+hn hp ROH, ROH, ROH Hn hp 18 sn phm.
* Phn ng ca ancol a chc: Phn ng este ha ca poliol c th to ra monoeste hoc polieste
ty thuc l l s mol gia axit v poliol. Th d:
+ Vi axit v c:
C
3
H
5
(OH)
3
+3HNO
3

20 C

2 4c
o
H SO
C
3
H
5
(ONO
2
)
3
+3H
2
O
Glyxerol trinitrat
Glyxerol trinitrat l mt cht n quan trng (thuc n an ton), thng c trn vi bt silic
oxit xp thu c sn phm c tn l iamit.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
12
+ Vi axit hu c:
- Vi axit n chc
Th d:
CH
3
COOH +C
2
H
4
(OH)
2
t C

2 4c
o
H SO
C
2
H
4
(OCOCH
3
)
2
+2H
2
O
CH
3
COOC
2
H
4
OH +H
2
O

RCOOH +
t C

2 4c
o
H SO
H
2
C
HC
H
2
C
OH
OH
OH H
2
C
HC
H
2
C
OCOR
OH
OCOR H
2
C
HC
H
2
C
OH
OCR
OCOR
H
2
C
HC
H
2
C
OCOR
OCOR
OCOR
H
2
C
HC
H
2
C
OH
OH
OCOR
H
2
C
HC
H
2
C
OCOR
OH
OH

Cc este vn cn nhm -OH trong phn t vn c cc phn ng nh mt ancol.
Khi cho poliol tc dng vi hn hp cc axit n chc sn phm to ra c th l este hoc hp
cht tp chc. Trong este c th l este do mt gc axit to ra cng c th l este do nhiu gc
axit to ra.
Th d 1: Hy vit cng thc cc sn phm c th c khi cho etylen glycol tc dng vi hn
hp gm axit axetic v axit fomic.
Th d 2: Hy vit cng thc cc trieste c th c khi cho glyxerol tc dng vi hn hp gm 3
axit RCOOH, RCOOH v RCOOH.
- Vi axit a chc: Sn phm c th l hp cht tp chc, este vng hoc polime nu trng ngng.
Th d 1:
HCOOC - CH
2
- COOH +
CH
2
CH
2
OH
OH CH
2
CH
2
OH
OCOCH
2
- COOH
+H
2
O

Sn phm to ra mang c chc axit, chc ru, chc este nn c th phn ng vi c mui,
ru, kim, kim loi kim,
Th d 2:
CH
2
CH
2
OH
OH H
2
C
H
2
C
+H
2
O
COOH
COOH
+
O
O
C
C
O
O

Th d 3:
nHOOCC
6
H
5
COOH +nHOCH
2
CH
2
OH [-CO-C
6
H
4
-COOCH
2
CH
2
O-]
n
+2nH
2
O
c) Bin php lm tng hiu sut phn ng este ha:
c im ca phn ng este ha l phn ng thun nghch, xy ra khi c xc tc l axit v c.
Phn ng xy ra chm, nn ngi ta thng un nng hn hp phn ng nhm gia tng tc phn
ng.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
13
lm tng hiu sut phn ng khng th dng bin php thay i nhit phn ng v hiu
ng nhit ca phn ng H0. M c th dng cc bin php sau:
- Tng nng axit hoc ru (dng d mt trong hai cht).
- Gim nng este hoc gim nng nc.
Ngi ta thng dng axit H
2
SO
4
c lm xc tc v H
2
SO
4
c va cung cp H
+
xc tc cho
phn ng, li va ht H
2
O lm gim nng H
2
O.
2.6.2.3. Phn ng tch H
2
O
Ancol c th tch H
2
O to ra cc sn phm khc nhau ty thuc vo c ch tch v cu to ca
ancol.
a) Hng tch loi
Hng ca phn ng tch loi ph thuc ch yu vo iu kin phn ng nh nhit , xc
tc,
* To ete:
-OH +HO-
o
2 4c,
H SO 140 C
-O- +H
2
O
Cng c th dng xc tc l Al
2
O
3
200
0
C.
* To anken:
C

C
o
2 4c
H SO ,170 C
C =C +H
2
O
H O
Xc tc c th dng l Al
2
O
3
400
0
C.
b) Phn ng tch loi H
2
O to ete t hai phn t ancol
R OH +HO R
o
2 4c,
H SO 140 C
R-O-R +H
2
O
- un nng mt ancol n chc thu c 1 ete n chc (i xng).
- un nng hn hp 2 ancol n chc ROH v ROH s thu c hn hp ete trong c 2 ete
i xng v 1 ete khng i xng.
2ROH
o
2 4c,
H SO 140 C
R-O-R +H
2
O
2ROH
o
2 4c,
H SO 140 C
R-O-R +H
2
O
ROH+ROH
o
2 4c,
H SO 140 C
R-O-R +H
2
O
- un nng n ancol n chc vi H
2
SO
4
c 140
0
C s thu c
n(n+1)
2
ete, trong n ete
i xng, cn li l cc ete khng i xng.
- Theo phng trnh ha hc ca phn ng:
_
2
ete H O ancol p
1
n =n = n
2
. V nh vy nu thu c
hn hp cc ete c s mol bng nhau th s mol ca mi ancol phn ng cng bng nhau.
- Theo nh lut bo ton khi lng:
2
ancol p ete H O
m =m +m
- Ta lun c M
ete
>M
ancol
, nn
ete
ete/ancol
ancol
M
d = >1
M
. C th dng du hiu ny nhn bit sn
phm ca phn ng tch nc.
c) Phn ng tch loi H
2
O to lin kt t mt phn t ancol
Ancol phi c t 2C tr ln v cn H C

mi c phn ng ny. Mi nhm chc OH tch

cng mt nguyn t H C

to thnh 1 phn t H
2
O.



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
14
* Ancol no, n chc bc I: Tch nc ch to thnh 1 anken duy nht:
Th d: CH
3
-CH
2
-OH
o
2 4c
H SO ,170 C
CH
2
=CH
2
+H
2
O
CH
3
-CH
2
-CH
2
-OH
o
2 4c
H SO ,170 C
CH
3
-CH=CH
2
+H
2
O
(CH
3
)
2
CH-CH
2
OH
o
2 4c
H SO ,170 C
(CH
3
)
2
C=CH
2
+H
2
O
* Ancol no, n chc bc II: Nu i xng th cho 1 anken, nu khng i xng th cho hn hp
cc anken (cha tnh ng phn hnh hc).
Th d:
CH
3
CH CH
3
OH
CH
2
CH CH
3

o
H SO ,170 C
2 4c
-H O
2

o
H SO ,170 C
2 4c
-H O
2
CH
3
CH CH
2
OH
CH
3
CH
2
CH
CH
2
CH
3
CH
3
CH CH CH
3

* Ancol no, n chc, bc III: Nu i xng s cho 1 anken, nu khng i xng s cho hn hp 2
hoc 3 anken (cha tnh ng phn hnh hc).
Th d:

o
H SO ,170 C
2 4 c
-H O
2
CH
3
C CH
3
OH
CH
3
CH
3
C
CH
2
CH
3

o
H SO ,170 C
2 4c
-H O
2
CH
3
CH
3
C CH
3
OH
CH
2
CH
2
CH
3
CH
3
C CH
2
CH
3
CH
3
C CH
3
CH

o
H SO ,170 C
2 4c
-H O
2
CH
3
CH
2
C CH
OH
CH
3
CH
3
CH
3
CH C
CH
CH
3 CH
3
CH
3
CH
CH
2
C CH
CH
3 CH
3
CH
3
CH
3
CH
2
C
C CH
3
CH
3
CH
3

Phn ng tch nc ca cc ancol bc II, III khng i xng tun theo quy tc Zaixep: Nhm
OH u tin tch cng vi nguyn t H C

c bc cao hn (tc c t H hn).

* Cc ancol khng no hoc ancol thm vn cho phn ng tch nc to ra sn phm c thm mt
lin kt :
Th d: CH
2
=CH-CH
2
-CH
2
-OH
o
2 4c
H SO ,170 C
CH
2
=CH-CH=CH
2
+H
2
O
C
6
H
5
-CH(OH)-CH
3

o
2 4c
H SO ,170 C
C
6
H
5
CH=CH
2
+H
2
O
Kt lun:
1- Mt ancol tch nc to thnh anken th ancol l ancol no, n chc. Chng minh:
C
n
H
2n+2-2k-a
(OH)
a

o
2 4c
H SO ,170 C
C
n
H
2n
+aH
2
O
ng nht s nguyn t H hai v ta c: 2n+2-2k=2n+2a
a =1 k >0 k <1. M k 0, nn k =0 a =1.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
15
2- Khi mt ancol tch nc ch thu c 1 anken th ancol l no, n chc, bc I hoc bc
II, III i xng.
3- Khi mt ancol mt nc thu c 2 anken (khng tnh ng phn hnh hc) th l ancol
no, n chc bc II hoc bc III khng i xng v 2 anken l ng phn cu to ca
nhau. Ancol bc II, hoc III i xng vn c th to ra 2 anken nu tnh c ng phn hnh
hc.
4- Mt anken mt nc cho 3 anken th trong 3 anken c ng phn hnh hc.
5- Hn hp 2 ancol tch nc cho 1 anken th 2 ancol l ng phn ca nhau s C >2.
6- Hn hp 2 ancol tch nc cho 3 anken th c 2 anken l ng phn ca nhau.
Ch :
1- Ancol metylic khng tham gia phn ng tch nc. Nn trong bi nu cho hn hp 2 ancol
tch nc m ch thu c 1 anken th phi tnh c trng hp hn hp c ancol metylic.
2- Trong phn ng lun c:
2
ancol p anken H O
n =n =n V:
2
ancol p anken H O
m =m +m
3- Ta lun c: M
ancol
>M
anken
, nn
anken
sp/ancol
ancol
M
d = <1
M
.
4- C
2
H
5
OH khi c xc tc c bit: Al
2
O
3
, 450
0
C th va tch loi H
2
O va tch loi H
2
to ra
buta-1,3-ien:
C
2
H
5
OH
2 3
450
o
Al O
C
CH
2
=CH-CH=CH
2
+H
2
O +H
2

d) Nguyn tc chuyn ancol bc thp thnh ancol bc cao hn: Thc hin lin tip hai phn ng
l phn ng tch nc ancol bc thp (theo Zaixep) ri cng nc vo anken thu c (theo quy tc
Maccopnhicop).
Th d: Vit cc phng trnh ha hc chuyn ancol 3-metyl-butan-1-ol thnh 2-metyl-
butan-2-ol.
CH
3
CH
CH
3
CH
3
C
H
CH
3
H
C CH
3
CH
3
C
CH
3
H
2
C CH
3
OH
CH
3
C
H
CH
3
H
C CH
2
CH
2
CH
2
OH
o
2 4c
2
H SO ,170 C
-H O

2
2 4
+H O
H SO

2
2 4
+H O
H SO
CH
3
C
H
CH
3
H
C CH
3
OH

o
2 4c
2
H SO ,170 C
-H O
CH
3
C
CH
3
H
C CH
3
HO

e) Phn ng tch nc ca ancol a chc:
Di tc dng ca cc cht ht nc mnh nh KHSO
4
, etylengylcol v glyxerol b mt nc
to thnh axetandehit v propenal.
H
2
C CH
2
OH OH
H
2
C
CH
OH
CH
2
=CH - CHO
km bn
KHSO
4
-H
2
O
CH CH
2
OH HO
H
2
C
OH
KHSO
4
-H
2
O
C CH
OH
H
2
C

f) Phn ng ph trong qu trnh tch loi nc
Khi dng H
2
SO
4
c lm xc tc, do H
2
SO
4
c c tnh oxi ha mnh nn ngoi phn ng
ehidrat ha cn c phn ng oxi ha ancol. Ancol c th b oxi ha thnh C (mui than), CO,
CO
2
; cn H
2
SO
4
b kh thnh SO
2
; cng c th xy ra phn ng este ha ancol vi axit H
2
SO
4
theo
2 nc. V vy trong qu trnh iu ch anken t ankanol, ngi ta phi dn hn hp sn phm ln
lt qua H
2
SO
4
c ( loi b hi nc, lm kh kh) ri qua bnh ng kim ( loi b CO
2
,
SO
2
).


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
16
2.6.2.4. Phn ng oxi ha
a) Phn ng oxi ha hon ton (phn ng t chy)
Nn vit phng trnh ha hc ca phn ng vi cng thc ancol dng thnh phn nguyn t.
C
n
H
2n+2-2k
O
a
+
3 1
2
n k a
O
2

o
t
nCO
2
+(n+1-k)H
2
O
Do cng thc phn t ca ancol c th coi l cng thc phn t ca hidrocacbon +vi a
nguyn t O nn t l s mol CO
2
v H
2
O to ra khi t chy ancol ging nh khi t chy
hidrocacbon tng ng:
- t chy mt ancol m cho s mol H
2
O ln hn s mol H
2
O th ancol phi l ancol no,
mch h (k=0); s mol ancol b t chy c xc nh theo cng thc:
2 2
ancol p H O CO
n =n -n

- Khi t chy mt ancol cho s mol CO
2
bng s mol H
2
O th ancol l ancol khng no, mch
h, c mt lin kt i.
- Khi t chy hn hp cc ancol m thu c s mol H
2
O ln hn s mol CO
2
th trong hn hp
c t nht mt ancol no, mch h.
- Khi xt t l:
2
2
O
CO
n
3n+1- k- a 1- (k+a)
T = = =1,5+
n 2n 2
. Do k+a lun lun nguyn dng nn 1-
(k+a) < 2. Do T 1,5. T ta c:
+Khi k +a =1(tc ancol no, mch h, n chc: k=0, a=1) th lun c T =1,5.
+Nu t chy mt ancol m c T =1,5 th ancol l ancol no, n chc, mch h.
+Nu t chy hn hp cc ancol m c T <1,5 th trong hn hp c t nht mt ancol khng phi
l ancol no, n chc, mch h.
b) Phn ng oxi ha khng hon ton
Ty thuc vo cu to ca ancol v tc nhn oxi ha cng nh iu kin tin hnh phn ng
m c th thu c cc sn phm khc nhau.
* Ancol bc I
l
l
l

O
andehit
l
l
l

O
axit:
R-CH
2
-OH +CuO
(en)

o
t
R-CHO +Cu
()
+H
2
O
Cht oxi ha y c th dng KMnO
4
, K
2
Cr
2
O
7
,
* Ancol bc II
l
l
l

O
xeton
oxi hoa manh
cc axit:
R CH R'
OH
+CuO
t
o
R C R'
O
+H
2
O +Cu

* Ancol bc III bn vi cc cht oxi ha trong mi trng trung tnh v mi trng kim, trong mi
trng axit n b oxi ha ct mch C thnh hn hp cc axit v xeton:
Th d:
H
3
C CH CH
2
OH
CH
2
CH
3
CH
2
CH
3
l
l l

O
CH
3
CH
2
COOH + CH
3
CH
2
C CH
3
O
CH
3
COOH + CH
3
CH
2
CH
2
C CH
3
O
+ HCOOH CH
3
CH
2
CH
2
C CH
2
O
CH
3

* Trong trng hp ancol bc I v bc II i qua ng kim loi nhit cao v thiu oxi khng kh
s xy ra phn ng hidro ha:
RCH
2
OH +O
2

o
Cu
450-500 C
RCHO +H
2



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
17
RCH(OH)R +O
2

o
Cu
450-500 C
RCOR +H
2

* Da vo sn phm oxi ha khng hon ton ca ancol c th phn bit cc ancol c bc khc
nhau: Ancol bc I cho sn phm c kh nng tham gia phn ng trng gng, ancol bc II cho sn
phm khng c kh nng tham gia phn ng trng gng.
* C th oxi ha ancol bng xc tc men:
C
2
H
5
OH +O
2

( )

men gim
Mycodermaaceti
CH
3
COOH +H
2
O
* Phn ng oxi ha khng hon ton ca ancol a chc
Ty theo iu kin oxi ha ta c th thu c cc sn phm l andehit, axit hoc kh CO
2
.
Th d:
HO-CH
2
-CH
2
-OH +CuO
o
t
HO-CH
2
-CHO +Cu +H
2
O
HO-CH
2
-CH
2
-OH +CuO
o
t
(CHO)
2
+Cu +H
2
O
CH
2
(OH)-CH(OH)-CHO
CH
2
(OH)-CH(OH)-CH
2
(OH)
[O]
CH
2
(OH)-CH(OH)-COOH
HOOC-CH
2
-COOH
2.6.3. Tnh cht ha hc ca ancol a chc
Ancol a chc hay poliol l nhng ancol c nhiu nhm OH lin kt vi cc nguyn t C no
khc nhau. Cc poliol c chia lm hai loi: loi c t nht 2 nhm OH nh 2 C cnh nhau v
loi khng c 2 nhm OH no 2C cnh nhau.
Hai poliol tiu biu l:

CH
2
OH
CH
2
OH

CH
2
OH
CH
2
OH
CH
OH

Etandiol (etylenglycol) Propatriol (glyxerol)
Do trong phn t c nhm chc OH nn cc poliol cng c nhng tnh cht ca ancol (tc
dng vi kim loi kim, phn ng este ha, tch nc, oxi ha). Tuy nhin, do trong phn t c
nhiu nhm chc nn khc vi cc ancol n chc, khi tham gia phn ng c th c hai kh nng
xy ra l:
+ Ch c mt hoc mt s nhm OH phn ng.
+ Tt c cc nhm OH u phn ng.
Vi cc ancol c cc nhm OH nh cc nguyn t C lin k, do nh hng qua li ca cc
nhm OH nn H cc nhm OH ny linh ng hn trong nhm OH ancol n chc v c
phn ng c trng vi Cu(OH)
2
to phc cht tan mu xanh da tri (dung dch xanh lam, trong
sut).
Th d:
H
2
C
H
2
C OH
OH HO CH
2
CH
2
HO
Cu
HO OH
O CH
2
CH
2
HO
H
2
C
H
2
C OH
O
Cu
-2H
2
O

H
2
C
HC OH
OH HO CH
2
CH HO
Cu
HO OH
O CH
2
CH HO
H
2
C
HC OH
O
Cu
CH
2
OH CH
2
HO CH
2
OH
CH
2
HO
-2H
2
O

Phn ng ny c dng nhn bit, phn bit cc poliol c 2 nhm OH lin k.



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
18
2.6.4. Nhn bit, phn bit cc ancol
2.6.4.1. Phn bit cc ancol khc bc
a) C th dng sn phmca phn ng oxi ha khng hon ton phn bit cc ancol bc I,
ancol bc II v ancol bc III:
+ Ancol bc I oxi ha cho sn phm l andehit, andehit c phn ng trng gng vi AgNO
3
/NH
3
.
+ Ancol bc II, trong iu kin oxi ha cho sn phm l xeton, xeton khng c phn ng oxi
ha.
+ Ancol bc III trong iu kin khng b oxi ha, nu dng cht oxi ha l CuO nung nng th
CuO khng b i mu vn c mu en.
Th d: Trnh by cch phn bit CH
3
CH
2
CH
2
OH v CH
3
CH(OH)CH
3
.
Gii
Ln lt cho hi ca hai ancol i qua CuO nung nng, ly sn phm cho vo dung dch
AgNO
3
/NH
3
, cht no c phn ng gii phng Ag th ancol tng ng l CH
3
CH
2
CH
2
OH, cht cn
li l CH
3
CH(OH)CH
3
.
b) Cng c th phn bit ancol cc bc bng thuc th Lucas, l hn hp HCl m c v ZnCl
2

khan. Khi cho thuc th Lucas vo ancol ta thu c dn xut clo tng ng, khng tan trong hn
hp phn ng v ty theo hm lng c th lm vn c hoc c hin tng tch lp:
R-OH +HCl R-Cl +H
2
O
+Ancol bc III phn ng nhanh nhit phng, c hin tng tch lp.
+Ancol bc II phn ng chm sau khong 5 pht, c hin tng vn c.
+Ancol bc I hon ton khng phn ng nhit phng, to dung dch trong sut.
2.6.4.2. Phn bit cc ancol c gc hidrocacbon khc nhau
Nu gc hidrocacbon c cc phn ng c trng, nh phn ng cng vi nc brom ca ancol
khng no, ta c th dng cc phn ng ny phn bit cc ancol.
Th d: Phn bit CH
3
CH
2
CH
2
OH v CH
2
=CH-CH
2
OH
Gii
Ln lt cho cc ancol vo bnh ng nc brom, ancol no lm dung dch brom nht mu th
l CH
2
=CH-CH
2
OH, cht cn li l CH
3
CH
2
CH
2
OH.
2.6.4.3. Phn bit cc ancol n chc cng dy ng ng
phn bit cc ancol n chc, cng dy ng ng v cng bc ta c th ly cng mt khi
lng ancol cho tc dng vi lng d Na (K,). Khi ancol no c M nh s c s mol ln do
lng H
2
to ra ln hn.
2.7. iu ch
2.7.1. iu ch ancol n chc
2.7.1.1. Hidrat ha anken
a) Hidrat ha trc tip
C
n
H
2n
+H
2
O
2 4 ng
o
H SO
t

lo
C
n
H
2n+1
OH
Phn ng ny tun theo quy tc Markopnicov cho sn phm chnh l ancol bc cao.
b) Hidrat ha gin tip (Dng H
2
SO
4
c)
Th d: H
2
=CH
2
+H
2
SO
4
CH
3
CH
2
OSO
3
H
2
100
o
H O
C
C
2
H
5
OH +H
2
SO
4

2.7.1.2. Thy phn dn xut halogen
Thy phn dn xut halogen trong mi trng kim:
R-X +NaOH
o
t
R-OH +NaX



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
19
2.7.1.3. Kh hp cht cacbonyl
a) Kh andehit hoc xeton
Cht kh c th dng rt a dng: H
2
/Pt (Ni), nhng tt hn c l LiAlH
4
v NaBH
4
v tc
nhn ny kh chn lc khng ng chm n lin kt bi.
- Andehit +H
2
Ancol bc I:
R-CHO +H
2

o
t
Ni
RCH
2
OH
- Xeton +H
2
ancol bc II:
R C R
O
+H
2
t
o
Ni
R
H
C R
OH

b) Kh axit v dn xut
Axit v dn xut ca n b kh bng LiAlH
4
to ra ancol vi hiu sut kh cao, vi cc axit,
dn xut khng no th lin kt bi vn gi nguyn.
Th d:
CH
3
(CH
2
)
7
CH=CH(CH
2
)
7
COOH
4
+
3
1.LiAlH ,ete
2.H O
CH
3
(CH
2
)
7
CH=CH(CH
2
)
7
CH
2
OH
CH
3
CH
2
CH=CH-COOCH
3

4
+
3
1.LiAlH
2.H O
CH
3
CH
2
CH=CH-CH
2
OH
2.7.1.4. T hp cht c magie
a) Phn ng vi HCHO ancol bc I
R-MgBr +HCHO
etekhan
RCH
2
OMgBr
+
3
+H O
-Mg(OH)Br
RCH
2
OH
b) Phn ng vi andehit ancol bc II
R-MgBr
1.+R'CHO, ete khan

+
3
2.H O
R-CH(OH)-R
c) Phn ng vi xeton ancol bc III
R-MgBr
1.+R'COR", etekhan

+
3
2.H O
R C R'
R"
OH

d) Phn ng vi dn xut ca axit ancol bc III
R-MgBr
1.+R'COZ, etekhan

+
3
2.H O
R C R
R'
OH
(Z l Cl, -OR, -OCOR)
2.7.1.5. Hidrobo ha oxi ha anken (to ancol bc thp)
R-CH=CH
2

3
2 2
1.BH
2.H O ,NaOH
R-CH
2
-CH
2
-OH
2.7.2. iu ch ancol metylic
CO +2H
2

o
ZnO
500 C,200atm
CH
3
OH
2.7.3. iu ch ancol etylic
2.7.3.1. T tinh bt hoc xenluloz
a) T tinh bt
(C
6
H
10
O
5
)
n
+nH
2
O
mantaz men
hay

2 4
amylaz v
H SO lo ng
nC
6
H
12
O
6
(glucoz)
C
6
H
12
O
6

o
men ru: zymaz
32 C
2C
2
H
5
OH +2CO
2



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
20
b) T xenluloz
(C
6
H
10
O
5
)
n
+nH
2
O
2 4
H SO c
ri pha lo ng
nC
6
H
12
O
6
(glucoz)
C
6
H
12
O
6

o
men
32 C
2C
2
H
5
OH +2CO
2

2.7.4. iu ch etylen glycol
- 3C
2
H
4
+2KMnO
4
+4H
2
O 3C
2
H
4
(OH)
2
+2MnO
2
+2KOH
- CH
2
=CH
2
+Cl
2
CH
2
Cl CH
2
Cl
2
3
+H O
NaCO
CH
2
(OH)-CH
2
(OH) +2HCl
2.7.5. iu ch glyxerol
a) Thy phn cht bo
H
2
C
HC OCOR'
OCOR
H
2
C OCOR"
H
2
C
HC OH
OH
H
2
C OH
+3NaOH +
RCOOH
R'COOH
R"COOH

b) Tng hp t propen
CH
2
=CH CH
3
+Cl
2

o
500 C
CH
2
=CH-CH
2
-Cl +HCl
CH
2
=CH-CH
2
-Cl +Cl
2
+H
2
O CH
2
Cl-CH(OH)-CH
2
Cl +HCl
CH
2
Cl-CH(OH)-CH
2
Cl +2NaOH
o
t
CH
2
(OH)-CH(OH)-CH
2
(OH) +2NaCl
c) Ln men glucoz c mt NaHSO
3

C
6
H
10
O
5

3
NaHSO
CH
2
(OH)-CH(OH)-CH
2
(OH) +CH
3
CHO +CO
2

3. PHENOL
3.1. Khi nim
Hidroxibenzen (C
6
H
5
OH) c tm thy khi ct phn on nha than . V mang tnh axit,
hp cht ny c gi l axit cacbolic hoc axit phenic, v v sau th hin nhng mi lin quan
vi cc ancol ngi ta gi n l phen-ol. Phen l tn c ca benzen.
Phenol l nhng hp cht hu c m phn t c cha nhm hidroxyl (OH) lin kt trc tip
vi nguyn t C ca vng benzen.
OH
OH
CH
3
OH
CH
3
OH
CH
3
OH
OH
hydroquinone
p-cresol
m-cresol o-cresol phenol

3.2. Cu trc
Lin kt O H phn cc v pha O, v trn nguyn t O cn cp electron n
(cp electron cha tham gia lin kt). Cp electron ny cng vi cc electron
vng benzen to nn mt h lin hp p- (hay n-). Trong :
- Nhm OH l nhm y electron lm tng mt electron trn nhn benzen,
c bit ti v tr o v -p, do lm tng tnh linh ng ca nguyn t H cc v
tr ny, lm chng d b th.
- Nhn benzen (C
6
H
5
-) ht electron rt mnh nh hiu ng lin hp n- lm cho
phn cc ca lin kt O-H tng ln (so vi ancol), do phenol th hin tnh axit yu.
- Lin kt C O phenol rt bn do cp e t do O dch chuyn v pha vng benzen lm cho
di lin kt C O b rt ngn li so vi lin kt C O ca ancol. Do phenol khng th phn
ng vi cc halogen hidric.
OH :


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
21
3.3. Phn bit, so snh phenol vi ancol thm
- Ging nhau: u c nhm OH v vng benzen.
- Khc nhau: Trong phenol, nhm OH lin kt trc tip vi nguyn t C ca vng benzen; trong
ancol thm, nhm OH lin kt trc tip vi nguyn t C no nhnh (Do s nguyn t C trong
ancol thm t nht phi l 7C).
- Th d: C
7
H
8
O c 1 ng phn l ancol thm (C
6
H
4
-CH
2
-OH)v 3 ng phn phenol (CH
3
-
C
6
H
4
-OH: o-, p-,m-).
3.4. Tnh cht vt l
- Phenol l cht rn kt tinh, khng mu, d b oxi ha trong khng kh thnh mu hng nht v
chy ra (do ht m).
- Nhit nng chy, nhit si tng i cao (43
0
C v 182
0
C) do lin kt hidro gia cc phn
t tng i bn vng.
- Phenol t tan trong nc lnh (mc du c kh nng to lin kt hidro vi nc nhng gc
C
6
H
5
- c tnh k nc cao), khi un nng tan tng.
- c, c tnh st trng, lm bng da.
3.5. Tnh cht ha hc
- Do c nhm OH nn phenol cng c nhng phn ng nh mt ancol (tc dng vi kim loi,
este ha).
- Do nh hng ht electron ca vng benzen nn nguyn t H nhm OH linh ng, do vy
phenol mang tnh axit yu pK
a
=1,3.10
-10
(tnh axit mnh hn nc th hai ca axit cacbonic, nhng
nh hn nc th nht pK
1
=4,5.10
-7
, pK
2
=4,7.10
-11
). Nn phenol phn ng c vi dung dch kim.
- Do nh hng y electron ca nhm OH nn mt e trong vng benzen tng (so vi
benzen), c bit l cc v tr p v o. Nn phenol d tham gia phn ng th vng benzen v
u tin th v tr o v p.
3.5.1. Tc dng vi kim loi kim
C
6
H
5
-OH +Na C
6
H
5
-ONa + H
2

Phenolat natri
Phenolat ca st to phc tan c mu tm:
6C
6
H
5
-OH +FeCl
3 (dd)
[Fe(OC
6
H
5
)
6
]
3-
+6H
+
+3Cl
-

Mu tm
Phn ng ny c dng nhn bit phenol
3.5.2. Tc dng vi dung dch kim
C
6
H
5
OH +NaOHC
6
H
5
ONa +H
2
O
Phenolat l cht rn mu trng, tan trong nc, khi tan in li ra ion C
6
H
5
O
-
l mt baz. Mui
phenolat c mt s nhng tnh cht sau:
+ Thy phn mt phn trong nc cho mi trng pH>7:
C
6
H
5
ONa C
6
H
5
O
-
+Na
+

C
6
H
5
O
-
+H
2
O C
6
H
5
OH +OH
-

+ Tc dng vi nhng axit mnh hn:
C
6
H
5
ONa +HCl C
6
H
5
OH +NaCl
C
6
H
5
ONa +CH
3
COOH C
6
H
5
OH +CH
3
COONa
C
6
H
5
ONa +CO
2
+H
2
O C
6
H
5
OH +NaHCO
3

Do phenol khn tang trong nc nn s c hin tng to kt ta hoc phn lp nu lng
phenol ln. Phn ng ny c s dng thu hi phenol hoc phn bit phenolat.



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
22
+ Tc dng vi cc axit khc dng ion:
C
6
H
5
ONa +NH
4
Cl C
6
H
5
OH +NH
3
+NaCl
3C
6
H
5
ONa +FeCl
3
+3H
2
O 3C
6
H
5
OH +Fe(OH)
3
+3NaCl
Nu d FeCl
3
s to phc mu tm [Fe(OC
6
H
5
)
6
]
3-
.
3.5.3. Phn ng th nhn thm
Do mt e trn nhn thm tng (so vi benzen) nn kh nng phn ng th vo nhn benzen
ca phenol tng v phn ng nh hng v tr o v p.
+ Phenol d dng phn ng vi dung dch brom ngay nhit thng:
+3Br
2
OH
OH
Br
Br
Br
+3HBr

2,4,6-tribrom phenol (kt ta trng)
+ Vi HNO
3
c:
+3HNO
3
OH
OH
NO
2 O
2
N
NO
2
+3H
2
O
H
2
SO
4

2,4,6-trinitro phenol (axit picric kt ta vng)
Axit picric c tnh axit mnh hn phenol (do c cc nhm NO
2
ht electron). N c dng
lm thuc cha bng, thuc n.
+ Phn ng ng trng ngng vi fomadehit:
+(n+1)HCHO
OH
+n+1()H
2
O
(n+2)
OH OH
H2
C
OH
H2
C
n

Poliphhenolfomandehit
Xc tc ca qu trnh ng trng ngng l kim hoc axit s thu c nha phenolfomadehit l
polime dng keo, c dng lm keo dn. Khi dng d HCHO v xc tc l axit ta s thu c 1
polime c dng mng li c gi l nha bakeli hay novolac, l cht rn kh nng chy v kh
bay hi.
OH OH
H2
C
OH
H2
C
H
2
C H
2
C
H2
C
H
2
C
H2
C
CH
2
H
2
C
CH
2
H
2
C
OH OH
OH



E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
23
3.5.4. Phn ng este ha vi dn xut ca axit cacboxylic
Do lin kt C-O rt bn vng nn phenol rt kh tham gia phn ng este ha vi axit (coi nh
khng phn ng), mun iu ch este ca phenol ngi ta phi dng dn xut ca axit cacboxylic
nh: clorua axit RCOCl, anhidrit axit RCOOCOR v kh nng phn ng ca cc dn xut ny cao
hn axit
C
6
H
5
OH +RCOCl RCOOC
6
H
5
+HCl
C
6
H
5
OH +RCOOCOR RCOOC
6
H
5
+RCOOH
Do phenol phn ng c vi dung dch kim nn khi thy phn este ca phenol trong mi
trng kim th t l phn ng khng phi l 1:1 na m l 1:2 v s khng thu c ancol. Th d:
RCOOC
6
H
5
+2NaOH RCOONa +C
6
H
5
ONa +2H
2
O
2.5.5. Phn ng chy
C
6
H
5
OH +7O
2

o
t
6CO
2
+3H
2
O
3.6. iu ch
3.6.1. T benzen
+Cl
2
Fe
-HCl
Cl
+NaOH/ t
o
,p cao
-NaCl
ONa
OH
+CO
2
-NaHCO
3

3.6.2. T cumen
+CH
2
=CH - CH
3
CH
OH
+O
2
CH
3
H
3
C
+CH
3
-CO-CH
3


B CC DNG BI TP
DNG 1. CC CU HI L THUYT
DNG 2. PHN NG VI KIM LOI KIM
Da vo d kin bi phi xc nh c ancol l ancol n chc hay a chc, no hay
khng no.
Cng thc tng qut:
+ Ancol no, n chc: C
n
H
2n+1
OH (n1, n nguyn)
+ Ancol no, a chc: C
n
H
2n+1-2a
(OH)
a
(2an; a, n nguyn)
+ Ancol khng no, c mt lin kt i, n chc: C
n
H
2n-1
OH (n3, n nguyn).
+ Ancol bt k: R(OH)
a

Phng trnh ha hc:
R(OH)
a
+aNa R(ONa)
a
+
2
a
H
2

Da vo t l s mol (th tch cng iu kin) gia H
2
v ancol phn ng ta s xc nh
ancol l n chc hay a chc (Bin lun nh 2.6.2.3)
Ch : Ngoi ancol, nhng hp cht c nguyn t H linh ng (phenol, axit) cng tc dng c
vi kim loi kim. Nn nu bi cho d kin hp cht hu c ch cha cc nguyn t C, H, O tc
dng vi kim loi kim cho H
2
bay ra, ta phi gi cng thc ca A dng (HO)
x
R(COOH)
y
sau
tm gi tr x+y v kt hp vi d kin khi lng phn t nu: M <76 th ch xt A l ancol
(phenol) hoc axit.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
24
Cc cng thc cn nh:
+ Theo nh lut bo ton khi lng:
2
ancol p Na ancolat H
m +m =m +m
+ Theo s tng gim khi lng:
R(OH)
a
R(ONa)
a
+
2
a
H
2

(R+17a)g (R+39a)g:
2
a
mol H
2
22 ( ) M a gam ^ =
Nn:
^
^
2
H
M
a= .2n
m

DNG 3. PHN NG TCH
Cn nh:
1- Nu sn phm to thnh c M
sp
<M
ancol
(Hoc 1 <
sp/ancol
d ) th sn phm l sn phm tch
ca 1 phn t H
2
O to thnh hp cht c thm 1 lin kt . Khi bin lun nh 2.6.2.3c.
Nu sau phn ng lm ngng t hi nc th do n
ancol
=n
anken
nn nu V, T khng i th p
cng khng i.
2- Nu sn phm to thnh c M
sp
>M
ancol
(Hay 1
sp/ancol
d ) th sn phm to thnh l ete.
Khi ta bin lun nh 2.6.2.3b.
Tch nc 2 ancol thu c 3 ete, trong c M
1ete
=M
1ancol
th s nguyn t C ancol ny
bng 2 ln s nguyn t C ancol kia: C
n
H
2n+1
OH v C
2n
H
4n+1
OH
3- t chy hon ton sn phm hu c thu c sau khi tch nc ancol thu c s mol
CO
2
nh khi t chy hon ton ancol (k c khi phn ng khng t hiu sut 100%).
DNG 4. PHN NG OXI HA KHNG HON TON
Cn ch:
1- Oxi ha ancol bc I cho andehit ri axit, nh lng andehit bng phn ng trng gng:
RCH
2
OH
[O]
RCHO
[O]
RCOOH
RCHO +2AgNO
3
+3NH
3

o
t
RCOONH
4
+2Ag +2NH
4
NO
3

2- Oxi ha ancol bc I c th cho hn hp cc sn phm gm: ancol d, andehit, axit, nc:




3- Oxi ha ancol bc II cho sn phm l xeton. C th nh lng xeton (v andehit) bng
phn ng vi NaHSO
3

RCHO +NaHSO
3
RCH(OH)(SO
3
Na)
RCOR +NaHSO
3
RC(OH)R(SO
3
Na)
Cc kt ta ny cho tc dng vi HCl s to ra SO
2

RCH(OH)(SO
3
Na) +HCl RCHO +NaCl +SO
2
+H
2
O
RC(OH)R(SO
3
Na) +HCl RCOR +NaCl +SO
2
+H
2
O
4- Khi cho oxi ha hn hp 2 ancol, sau cho sn phm to ra phn ng vi AgNO
3
/NH
3

d thu c s mol Ag: n
Ag
<2.n
hh ancol
iu chng t hn hp 2 ancol c 1 ancol bc II, hoc
bc III.
5- Ancol bc III khng b oxi ha trong iu kin tng t.
+NaOH
Trng gng
+Na
dd RCH
2
OH
[O]
dd X
RCHO +H
2
O
RCH
2
OH +H
2
O
H
2
O ca dd u
RCOOH +H
2
O
Tt c p, tr RCHO
Ch RCHO p
tr TH axit l HCOOH
Ch RCOOH p


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
25
6- Oxi ha hn hp 2 ancol no, n chc mch h cho 2 axit tng ng trong 1 axit c M =
M ca mt trong 2 ancol ban u, chng t hn hp ban u l hn hp 2 ancol ng ng k tip
nhau.
RCH
2
OH
[O]
RCOOH
R +31 R +45 14 M ^ =
7- C th p dng s tng gim khi lng gia sn phm thu c sau khi oxi ha vi ancol:
RCH
2
OH
[O]
RCHO
R +31 R +29 2 M ^ =
8- Khi t chy hon ton sn phm sau khi oxi ha s thu c s mol CO
2
nh khi t chy
hon ton ancol.
DNG 5. PHN NG CHY
Cn nh:
1- Cng thc ca ancol c th coi l cng thc ca hidrocacbon tng ng thm a nguyn t O
(a l s nhm chc ancol). Do s nguyn t H lun chn v t l s mol CO
2
vi s mol H
2
O
tng t nh khi t chy hidrocacbon.
C
x
H
y
O
z
+
o
t
x y z 2 2 2
y z y
C H O +(x+ - )O xCO + H O
4 2 2

Hay:
o
t
n 2n+2-2k a 2 2 2
3n+1- k- a
C H O + O nCO +(n+1- k)H O
2

2- Theo nh lut bo ton khi lng:
2 2 2
2 2
ancol O p CO H O
O/ancol O p O/CO O/H O
m +m =m +m
m +m =m +m

3- t chy mt ancol m cho s mol H
2
O ln hn s mol H
2
O th ancol phi l ancol no,
mch h (k=0); s mol ancol b t chy c xc nh theo cng thc:
2 2
ancol p H O CO
n =n -n

4- Khi t chy mt ancol cho s mol CO
2
bng s mol H
2
O th ancol l ancol khng no,
mch h, c mt lin kt i hoc ancol 1 vng no.
5- Khi t chy hn hp cc ancol m thu c s mol H
2
O ln hn s mol CO
2
th trong hn
hp c t nht mt ancol no, mch h.
6- Khi xt t l:
2
2
O
CO
n
3n+1- k- a 1- (k+a)
T = = =1,5+
n 2n 2
. Do k+a lun lun nguyn dng nn
1-(k+a) < 2. Do T 1,5. T ta c:
+Khi k +a =1(tc ancol no, mch h, n chc: k=0, a=1) th lun c T =1,5.
+Nu t chy mt ancol m c T =1,5 th ancol l ancol no, n chc, mch h.
+Nu t chy hn hp cc ancol m c T <1,5 th trong hn hp c t nht mt ancol khng phi
l ancol no, n chc, mch h.
DNG 6. TON V ANCOL A CHC
Cn nh:
1- Xc nh s nhm OH da vo phn ng vi kim loi kim:
R(OH)
a
+aNa R(ONa)
a
+
2
a
H
2

+ C bao nhiu nhm OH th cn tng y Na: n
Na
=a.n
ancol

+ Khi
2
H ancol
n n th ancol l ancol a chc.


E:\Mr He\GIAO AN\CHUYEN DE\DAN XUAT HALOGEN - ANCOL - PHENOL.doc
26
+ Nu hn hp 2 ancol phn ng vi kim loi kim, chng minh 1 trong 2 ancol l ancol
a chc ch cn chng minh:
2
1
2
H hhancol
n n

.
+ C th s dng s nhm OH trung bnh trong cc bi ton hn hp ancol:
OH
OH
ancol
n
n
n
=
_
_

Nu tnh c 1 2
OH
n < < th hn hp c t nht 1 ancol n chc v t nht mt ancol a
chc.
2- Xc nh cng thc cu to ca poliol da vo phn ng vi Cu(OH)
2
: poliol c hai nhm
OH lin k ha tan c Cu(OH)
2
to phc tan mu xanh.