Bo Co Thc Hnh Ha Hu C

GVHD: Nguyn Quang Khuyn

Bi 11:
IU CH AXETANILIT
Gio vin hng dn

: Nguyn Quang Khuyn

Ngy lm th nghim

: 13/04/2009

Lp

: HHO3

H tn sinh vin

: Nguyn Mnh Hng

Nhm: 7
0770830

: Nguyn Th Hng
: Nguyn Th Cm Hng
: Phm Th Lan Hng
Nhn xt:................................................................................................................
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1. MC CH TH NGHIM
iu ch axetanilit bng phn ng acyl ha
2. CHUN B L THUYT
1) Phn ng acyl ha: l qu trnh thay th nguyn t H nhm chc OH,

NH2, bng nhm RCO

Phn ng acyl ha l phn ng c trng ca amine thm. Phn ng trong
khng nhng cn amine c tnh bazo mnh m cn i hi trn nguyn t
nitrogen phi c proton.
Cc amimine bc mt v bc hai c kh nng tham gia phn ng vi cc dn xut
acid chloride (clorua) hoc anhydride hnh thnh cc amide tng ng. Trong khi
cc amine bc ba khng tham gia phn ng ny do khng cn proton trn
nguyn t nitrogen
1

SVTH: Nhm 7

Bo Co Thc Hnh Ha Hu C

GVHD: Nguyn Quang Khuyn

H

RCOOH

NH2

H2O

Tc nhn acyl ha thng dng: CH3COCl, (CH3CO)2O, hay CH3COOH.

mnh yu ca tc nhn acetyl nh hng ln n kh nng v tc phn ng
V d: mun iu ch acetanilide t aniline. Trong trng hp ny c th s dng
tc nhn acyl ha l acetic acid, tuy nhin phn ng s thun nghch v tc phn
ng chm hn nhiu so vi trng hp acetyl chloride hoc acetic anhydrire.
2) C ch phn ng:
C ch phn ng acyl ha amine xy ra nh sau, trong i hi phi c proton
trn nguyn t nitrogen ca amine. Khc vi phn ng alkyl ha, cc amide sinh ra
khng c kh nng tip tc tham gia phn ng acyl ha, do i in t nitrogen

tham gia lin kt vi nhm C

O.
O

NH

C
O

H2 O

OH

OH
C

OH

3) ng dng phn ng acyl ha amine thm trong vic to thnh hp cht

amide:

Bo v nhm NH3 trong cc phn ng tng hp hu c. Do kh nng d

dng b thy phn khi c mt cht xc tc acid hoc kim ti to amine

V d: mun iu ch p-nitroaniline t aniline, cn phi bo v nhm NH 2 trc
khi thc hin phn ng nitro ha trnh phn ng oxi ha gc NH2.

SVTH: Nhm 7

Bo Co Thc Hnh Ha Hu C

GVHD: Nguyn Quang Khuyn

H

NH2

H3C

COOH

H2O

CH3

HNO3/H2SO4
H
O2N

NH2

H2O/H+
to

O2N

C
O

p-nitroaniline

CH3

Ngoi ra, phn ng acyl ha cn s dng gim hot nhm NH 2 v tng

t l sn phm th para- trong cc phn ng th i in t vo nhn thm

V d: phn ng iu ch p-bromoaniline. Phn ng brom ha trc tip aniline s
cho sn phm 2,4,6-tribromoaniline. Tuy nhin sau khi gim hot nhm NH 2 bng
phn ng acyl ha, s thu c sn phm chnh l p-bromoaniline.
H
NH2

H3C

COOH

H2O

CH3

AlCl3 Br2
H
Br

NH2

H2O/H

to

Br

CH3

p-bromoaniline

3. GII THCH CC HIN TNG: TRONG TH NGHIM

C ba giai on chnh xy ra trong qu trnh tin hnh th nghim:
Giai on 1: acyl ha aniline bng acid axetit
Thao tc: (3,8g natri axetat + 80ml nc ct) + 2,3g anilin + 2,8ml HCl m c +
un cch thy 50oC. Phn ng din ra trong becher 250ml
Phn ng ha hc:
NH2

CH3COONa

HCl

50o

H
N

CH3

NaCl

H 2O

(1)

axetanilit

Mt t anilin khng tan ht vo dung dch Anilin phn ng khng hon ton
trong phn ng (1). Ta bit natri axetat l mui c to t acid axetit, y l mt
loi acid carboxylic yu chnh v vy phn ng din ra thun nghch, tc phn
3

SVTH: Nhm 7

Bo Co Thc Hnh Ha Hu C

GVHD: Nguyn Quang Khuyn

ng chm v cn cht xc tc acid mnh. iu ny gii thch v sao anilin khng

tan hon ton trong dung dch.
V li, phn ng (1) xy ra thun nghch nn s to li aniline l vic bnh thng.
Giai on 2: acyl ha aniline bng anhydrit axetic
Thao tc: sn phm phn ng (1) + 3ml anhydrit axetic lc u, gi nhit
50oC trong thi gian 30 pht khy, lm lnh lc, ra bng nc lnh
Phn ng ha hc:
O
H3C

C
O

NH2
H3C

50o

(2)

CH3COOH

axetanilit

CH3COOH

H
N C CH3
O

50o

NaCl

CH3COONa

HCl

(3)

Anhydrit axetic c bn cht l mt acid v mnh hn cc acid carboxylic, nn phn

ng acyl ha mnh hn cc acid carboxylic v phn ng 1 chiu khng ti to li
aniline. Do sau 30 pht aniline phn ng hon ton, th hin bng vic ta
khng cn nhn thy cc git nh git du khng tan trong dung dch.
Khy v lm lnh gip axetanilit kt tinh li dng tinh th khng mu. V ra li
bng nc lnh, tuyt i khng s dng nc si v nc si s lm axetanilit tan.
V axetanilit thu c s khng hon ton sch nn pht sinh giai on 3
Giai on 3: Tinh ch sn phm
Dng nc si ha tan sn phm th giai on 2 khy cho n ht sn phm
tan nu sn phm cn mu th thm 2g than hot tnh vo un si khong 5
pht lc thu tinh th lm lnh lc thu sn phm tinh khit
Bn cht ca than hot tnh l hp th cc tp cht nh hin tng hp th trn b
mt than hot tnh hp th cht to mu dung dch axetanilit tan trong nc
tinh khit.

SVTH: Nhm 7

Bo Co Thc Hnh Ha Hu C

GVHD: Nguyn Quang Khuyn

4. TNH HIU SUT CA PHN NG:

O
H3C C
0.025

0.025

NH2
H3C

50o

0.025

CH3COOH

axetanilit

CH3COOH

H
N C CH3
O

50o

NaCl

CH3COONa

HCl

Ta c: naniline = 0,025 mol

Cho ta naxetanilit = 0.025 mol mlt axetanilit = 3,375g
Thu c:

1.34 (g) Axetanilit sau th nghim

Hiu sut phn ng: H = (1.34/3.375).100 = 39.7 (%)

SVTH: Nhm 7