Bai tap hoa hoc ALDEHYD VÀ CETON ACID

ALDEHYD VÀ CETON ACID
1. Viết công thức:

2. Gọi tên:

Acid glyoxalic
Acid acetylacetic

CH 3 C COOH
O
OHC COOEt

Acid levulic

OHC CH 2 COOH

Ethylformylacetatnatri

OHC CH 2 CH 2 COOEt

Acid pyruvic
3. Viết phương trình phản ứng thủy phân:
Br

H2O/HO

CH 3 C COOH

CH 3 C COOH

Br

O

CH 3 O CH 2 CH

CO OCH 3

Cl
H C COOC2H 5
Cl

H2O/HO

CO OCH 3

H2O/HO

CH 3 O CH 2 CH

H C COOH
O

COO H
COO H

CO2

CH 3 O CH 2 CH 2 COO H

4. Điều chế Acid pyruvic từ Acid propionic:

Br2 / P

CH 3CH 2COOH

CH 3CHBrCOOH NaOH CH 3CHOHCOOH

[O]

CH 3 C COOH
O

5. Điều chế các hydroxy acid tương ứng:
HO CH2 CH2 CN
CH 3 CHOH COOR

2 H2O/H+
NaOH

HO CH2 CH2 COOH
+

H

CH 3 CHOH COONa

CH 3 CHOH COOH

6. Thực hiện kiểu ngưng tụ Claisen cho các hợp chất:

2 CH 3 CH 2 CH 2 C OC3H 7

O

2

CH 2 COOC2H 5
CH 2 COOC2H 5

HO
C2H5OH

HO
C3H7OH

C 2H 5
CH 3 (CH 2)2 C CH C OC3H 7
O

CH 2 COOC2H 5
CH 2 C CH COOC2H 5
O CH 2 COOC2H 5

O


7. Thực hiện phản ứng của Acid levulic:
H2/Ni

H 3C CH CH 2CH 2COOH
OH

CN
HCN

H 3C C CH 2CH 2COOH
O

H 3C C CH 2CH 2COOH
OH
SO 3Na

NaHSO3

H 3C C CH 2CH 2COOH
OH

H2N NH C 6H5

H 3C C CH 2CH 2COOH
N NH C 6H 5

8. Viết cơ chế phản ứng giữa acid glyoxalic và acid succinic. Gọi tên sản phẩm:

CH 2 COOH
CH 2 COOH

HO
H2O

O
HOOC CH CH COOH

CH COOH
HOOC CH O

CH 2 COOH

CH 2 COOH
H2O

HOOC CH C COOH

OH
HOOC CH CH COOH

H2O

CH 2 COOH

CH 2 COOH

Acid 1-propen-1,2,3-tricarboxylic

9. Giải thích cơ chế giữa acid pyruvic và AgNO3/NH3. Gọi tên sản phẩm:
H 3C C COOH AgNO3/HNO3 CH 3COOH
O
CH 3 C COO H
CH 3 C H

O

+ CO 2

+ Ag

CO 2

+

O

CH 3 C H
O

AgNO3/NH 3

CH 3 COO H

+

Ag

10. Cho biết thuốc thử của chuỗi phản ứng:

O

a)
b)

LiAlH4/H3O

+

POCl 3. pyridin

c)
d)

KMnO4

C 2H5OH/H

+

COOEt
COOEt

O
e) NaOEt
f) H3O+

COOC 2H 5


11. Qui trình tổng hợp acid bucloxic (chất kháng viêm). Cho biết xtác và tác nhân phản ứng của từng giai
đoạn:
O
COOH

O
+

O
O

O

A lC l 3

C l 2/Fe C l 3

COOH
Cl


ALDEHYD VÀ CETON BÉO
1. Gọi tên:
CCl3 CH O
Tricloroetanal
Tricloroacetaldehyd
Cloral

CH2 CH CHO
Propenal
Acrolein

CH3 CH CH CHO
2-butenal
Crotonaldehyd

(CH3) 2 C CH CH2 CO CH3

CH3 CO CH CH2

C6H5 CH2 CH2 CHO

Methylvinylceton

3-phenylpropanal

CH3 CH(OCH3) 2
1,1-dimethoxyetan

CH3 CO CH2 CHO
3-oxobutanal

5-methyl-4-hexen-2-on

CH3 CO CH2 CO CH3
2,4-pentandion
Acetoaceton

Acetoacetandehyd

O
HO

OH
OCH3

OCH3

2,6-di- (4'-hydroxy-3'-methoxybenzyl)
cyclovalon

cyclohexanon

(thuoác lôïi maät)
Cl
N H C H 3 .H C l
O

2- (2'-clorophenyl)

-2- (methylamino)
Ketamin

1

1'

O HO
6

cyclohexanon

CH3
2'

6-[ (R) -2'-hydroxy-6'methylhept-5'-en-2'-yl) cyclohex-2-enon
Hermandulcin

OHC CHO
Etandial
Glyoxal


2. Viết công thức các chất sau:

3. Aldol hóa:

4. Viết các quá trình chuyển hóa:


5. Điều chế butanon:


6. Điều chế aceton:
a.
CH 3CH 2OH CuO
CH 3CH 2OH

CH 3CHO
+

KMnO4/H

b.

CH 3CH 2CH 2OH

CH CH

7.
a.

b.

c.

d.

2) H2O/H+

CH 3COOH

H2SO4ññ ,1800C
H2O

[O]

CH 3 CHOH CH 3

Ca (OH) 2

(CH 3COO) 2Ca

CH 3 CH CH 2

H2O

t0

CH 3COCH 3
CH 3COCH 3

CaCO3

CH 3 CHOH CH 3
[O]

CH 3COCH 3

c.
CH CH

1) CH3MgI

Na

CH C Na

H2O
HgSO4/H2SO4

CH3I

CH 3CHO

CH C CH 3

1) CH3MgI
2) H2O/H+

+

H2O/H

CH 3COCH 3

CH 3 CHOH CH 3

[O]

CH 3COCH 3


e.
2 CH3CHO

HO
H2O

CH3 CH CH CHO 2CH3CH2OH CH3 CH CH CH(OC2H5)2
H2/Ni

H2O

CH3CH2CH2CH(OC2H5) 2

CH3CH2CH2CHO

[O]

CH3 C CH2 CH3
O

f.
2 CH 3CHO

g.

CH 3CHO

HO
H2O

C2H5MgCl

CH 3 CH CH CHO

CH 3 CH CH 2 CH 3

+

H2O/H

CH 3CHOHCH 2CH 3

OMgCl
[O]

CH 3 C CH 2 CH 3

h.

i.

O

CH 3 CHO C 2H5MgCl
H 2SO4ññ ,180 0C
H 2O

k.

CH 3
KMnO4

CH 3CHO

+

CH 3 CH CH 2 CH 3 H2O/H
CH 3 CHOHCH 2 CH 3
OMgCl
2 NaNH 2/NH 3
CH CH CH 3 Br2
CH 3 CH CH CH 3
Br Br

CH 3COOH

H2/Ni

+

H

C2H 5OH

CH 2 CH CH CH 2

CH 3COOC2H 5

8. Hoàn thành chuỗi phản ứng:
a.
C2H 5 CH CH 2 CH 2 Br
CH 3
NaOH dd

KOH/alcol

C2H 5 CH CH CH 3
CH 3 OH

3-methyl-2-pentanol

[O]

C2H 5 CH CH CH 2
CH 3

HCl

3-methyl-1-penten

C2H 5 CH CH CH 3
CH 3 Cl

2cloro-3-methyl-1-penten

C2H 5 CH C CH 3
CH 3 O

3-methyl-2-penanon
C6H5NHNH2

C2H 5 CH C CH 3

CH 3 NNHC6H 5
3-methyl-2-pentanonphenylhydrazon


b.
(CH3)2CH C CH3
O

[H]

(CH3)2CH CH CH3 HBr (CH3)2CH CH CH3
OH

Br
Mg/ether khan

(CH3)2CH CH CH3 HCHO (CH3)2CH CH CH3
MgBr

CH2OMgBr

2-magnebromid-3-methylbutan 2,3-dimethyl-1-oxymagnebromidbutan
+

H2O/H

(CH3)2CH CH CH3
CH2OH

c.

2,3-dimethyl-1butanol
Br2

CH 3 CH 2 CH CH 2

CH 3 CH 2 CH CH 2 2KOH/alcol

NaNH2/NH3

H2O
++

Br

CH 3 CH 2 C CH

Br

CH 3 CH 2 C C Na

CH3I

natributynylid

+

Hg /H

CH 3 CH 2 CH C CH 3

CH 3 CH 2 C C CH 3

CH 3 CH 2 CH 2 C CH 3

OH

O

d.
O C 6H 5NH 2

N C 6H 5

N H C 6H 5

LiA lH 4

ClCH 2CH 2CH 2N (C 2H 5) 2
NaNH 2

N CH 2 CH 2 CH 2 N (C 2 H 5 ) 2
C 6H 5

e.

Cl CH 2 C O
CH 3

1)

C2H5MgBr

2)

+

H2O/H

Cl CH 2

C 2H 5
C 2H 5

C6H5COCl
C OH
Cl CH 2 C O C C6H 5
CH 3
CH 3 O

1-cloromethyl-1-methylpropylbenzoat

HN(CH3)2

CH 3
CH 3

N CH 2

C 2H 5
C O C C 6H 5
CH 3 O

1-N,N-dimethylaminomethyl-1-methylpropylbenzoat
9. Phân biệt:

CHI3

khoâng coù pöù haloform

CH 3COOK

KI

+

KOH

+

CH 3CH 2CHO

I2

+

CH 3 C CH 3
O

+

Haloform

+

a.

H 2O


b.

CH 3 C

H aloform

H

O
CH 3 CH 2 CH O

c.

CH I3
khoõng coự pửự haloform

2,4-dinitrophenylhydrazin
NO2
O2N

C O

CH3

CH3
CH3

NO2

CH3

C N NH

CH3

CH OH

Isopropanol
d.

NHNH2

Cl
C H 3 C C 3H 7

Lucas
HCl / ZnCl2

t

CH3
CH3

o

H 2O/HO

H2O

CH Cl
tuỷa traộng

C H 3 C C 3H 7

Cl

NO2

+

CH3

cho pửự haloform

O

2,2-dicloropentan
C 2H 5

Cl
C C 2H 5
Cl

H 2O/HO

C 2H 5

C C 2H 5
O

khoõng cho pửự haloform

3,3-dicloropentan
10. iu ch pentaerythritol. Gi tờn theo IUPAC:

CH 3 CHO

H CHO
HO

CH 2 CHO
CH 2OH

2 H CHO
HO

CH 2OH
HOCH 2 C CHO
CH 2OH
H CHO/ HO

+

HOCH2

CH2OH
C CH2OH
CH2OH

HCOO

2,2-di(hydroxymethyl)propan-1,3-diol


ALDEHYD VÀ CETON THƠM

1. Gọi tên

CHO

CHO
Cl

CHO

S O 3H
m-formylbenzensulfonic
m-sulfobenzaldehyd

NO2
2-cloro-4-nitrobenzaldehyd
CH

CH

OCH3
OH
3-methoxy-4-hydroxybenzaldehyd
vanilin

CHO

CH3

 -(p-tolyl) acrolein

CO CH 3
methylphenylceton
acetophenon

CO CH CH 2
phenylvinylceton

3-(p-tolyl) propenal
p-methylcinamaldehyd

Ethyl-p-methoxyphenylceton

CH3 C N OH
acetophenoxim
methylphenylcetoxim

CHO

CH3

CHO
9,10-formylanthracen

C
O
Di(p-tolyl) ceton

CH3

p,p'-dimethylbenzophenon

anthracen-9,10-dicarbaldehyd
O

2-formylthiophen
S

O
anthraquinon
anthracen-9,10-dion

CHO

thiophen-2-carbaldehyd

C
N (CH 3 )2
O
di-(p-dimethylaminophenyl) ceton

(H 3 C)2 N


2. Viết công thức:

CH O
Cl

C
CH 3

O
phenyl-p-tolylceton

O 2N

CH O

p-nitrobenzaldehyd

o-clorobenzaldehyd

CH 3 C

Br

O
acetophenon

(H 3 C)2 N

Br

C

O
4,4-dibromobenzophenon

p-dimethylaminobenzaldehyd

3. Điều chế dựa trên phản ứng acyl hóa theo Friedel-Crafts:

+

AlCl 3

(CH 3CO)2O

+

CH 3 C

CH 3COOH

O
acetophenon

+

CH 3

C Cl

AlCl 3

CH 3

+

O

+

(CH 3CH 2CO)2O

O

AlCl 3

CH 3CH 2 C

+

CH 3CH 2COOH

O
ethylphenylceton
+

CH 2COCl

AlCl 3

CH O

CH 2 C
O
phenylbenzylceton

+

HCl

4. Viết phản ứng:
HCN

H 3C

OH
CN

CH

Cyanohydrin-p-tolylaldehyd
NaHSO3

H 3C

CH

OH
SO 3 Na

Bisulfitic p-tolylaldehyd
H 3C

C 6H 5NH 2
H 2O

CH O

H 3C

CH

N

C 6H 5

N-phenyl-p-tolualdimin
N (C H 3 ) 2
C 6H 5 N(C H 3)2

H 3C

H 2O

CH
N (C H 3 ) 2

p-tolyl-di-p-(N,N-dimethylaminophenylmethan

p.p’-dimethylbenzoin
CH C
OH O

H 3C

CH 3

KCN/alcol

H 3C

CHO

PCl 3
POCl 3

H 3C

Cl

Cl
Dichloro-p-tolylmethan

(CH3CO)2O/CH3COONa
CH3COOH

2 C2H5OH
H2O

CH

H 3C

CH CH COOH

3-p-tolylpropenoic

H 3C

CH

OC2H 5
OC2H 5

p-tolyl-diethoxymethan
NaOH ñaëc

H 3C

COONa + H 3C

CH3COCH3

CH 2OH

H 3C

CH CH C CH 3
O
4-(p-tolyl)-3-buten-2-on


5. Phân biệt:
- Acetaldehyd và benzaldehyd:

pứ haloform

- p-tolylaldehyd và acetophenon: -pứ haloform

-tt Schiff, Tollens, Fehling
6. Từ toluen điều chế p-nitrobenzaldehyd và viết phản ứng Cannizaro và Benzoin:
H 3C

HNO3 + H2SO4

H 3C

2 Cl 2/aù s

NO 2

Cl
CH
Cl

NO 2
H2O/HO

OHC

NO 2

p-nitrobenzaldehyd

O 2N

NaOH ñaëc

O 2N

COONa + O 2N

KCN/alcol

O 2N

CH C

CH 2OH

CHO
NO 2

OH O

7. Từ benzen điều chế p-clorobenzaldehyd. Viết phản ứng ngưng tụ với propionaldehyd, methylethylceton,
annhydrid acetic:
Cl
2 Cl 2/as
Cl 2
CH3I
CH 3
Cl
CH 3
Cl
CH
AlCl 3
Fe
Cl

2 H2O/HO

Cl
CH3CH2CHO/HO
H2O

Cl

CHO

CH3COCH2CH3/HO
H2O

Cl

CH 3

Cl

(CH3CO)2O/CH3COONa
CH3COOH

CH C CHO

CH CHCOCH 2CH 3

Cl

CH CH COOH

CHO


8. Từ p-methoxybenzaldehyd điều chế:
a. CH3O

CHO HCN

CH 3O

2 H2O/H+

CH CN

CH 3O

CH COOH

OH

OH
NH3

CH 3O

c. CH 3O

CHO

b. CH3O

CHO C2H5MgBr CH 3O

d. 2 CH3O

KCN + NH4Cl

CH 3O

CH COOH
NH 2

H3O+

CH CN
NH 2

CHO

H2N NH2
2 H2O

H O+

3
CH C2H 5
CH 3O
MgBr(OH)
OMgBr

CH 3O

CH N N CH

CH C2H 5
OH

OCH 3

9. Thực hiện chuyển hóa:
CH3

a.

C H C l2
2 C l2 / a s

OH

CHO

CHO

H 2O/H O

OH

CHO
C H 3I

Na

OH

ONa

OCH3
COOK
+

KOH

b.

OCH3
CH3

C H C l2
2 C l2 / a s

OCH3

CHO
H 2O/H O

KC N/a lco l

CH

C

OH

O

[O]

CHO
C l 2/Fe

c.

C H 2O H

C

C

O

O

CHO

Cl

C 6H 5C H 2ONa

O C H 2C 6H 5

C 6H 5

CHO

CH OMgBr
C 6H5MgBr

H2O/H

C 6H 5 CH

OH

+

C 6H 5 C O
CrO3

C 6H 5 C N
NH2OH

OH
H2O/H

O C NH C 6H 5
+


d.

C 2H 5 C

O

C 2H 5
1) C H 3M g I

C 2H 5C OC l
A lC l 3

2)

O

O3

e.

O

Mg
ether khan

H 2O/Z n

OMgCl
CH CH 2C6H 5

Br2

C6H 5 CH CH C6H 5

KOH/alcol

10. Từ benzen điều chế vanilin:
Cl
Cl2 / Fe

OCH 3
OH

OH
o

t ,p

CH3I
AlCl3

CH 3O

OCH 3
OH

CH 3

CHCl2

C6H 5NH 2

H2O

gaiacol

CHO

vanilin
HO
CH 3O

CH N C6H 5

11. Hoàn thành qui trình điều chế:
a. Bisacodyl: Nhuận tràng:
HO

OH

H H
O
N

C H

H2SO4

HO

OH
N

C

H

AcO
(CH3CO)2O

OAc
N

C

H

+

H2O/H

C C 6H 5

OCH 3
OH

H2O/HO

C H 3C H O

Br Br
CH CH C6H 5

OCH 3
OH

Cl2
O
2) NaOH , t ,p

OCH 3
OH 2
Cl2 / aù s

+

CHO

C 6H 5 C

1)

HO

HO

C 6H 5

OCH 3
CH3I

NaOH

+

C CH3
O

C6H5CHO

CH 2MgCl

OH
CH CH 2 C6H 5 H2SO4

C 6H 5

H 2O/H

CH3 C CH CH3
H 2SO 4

+

C
CH CH3
O
CH3

CH 2Cl

CH3

C OH


b. Các Vitamin K:
CH 3

O

CH 3

CrO3
Ac2O

N OH
CH 3

NH2OH (1 mol)

O

O
ClCH2COONH4

Zn/HCl

OH

N OCH 2COOCH 4
CH 3

CH 3

OH

O

c. Haloperidol: An thần:
N
H

OH

F
Cl (CH 2)3 C Cl
O

+

Cl

F

OH

Cl

AlCl3

N
(CH 2)3 C

O

O C (CH 2)3 Cl

F

d. Progabid: Trị động kinh:
OH
F

CH OH

OH
CrO3

F

OH

H2N (CH2)3 C NH2
O

C O

F

C N (CH 2)3 C NH 2
O

Cl

Cl

Cl

e. Amfepramon: Thuốc gây chán ăn:
C 2H 5COCl
AlCl 3

O
C CH 2 CH 3

Br 2

HN(C 2H 5)2

O
C CH Br
CH 3
O
C CH N (C 2 H 5 )2
CH 3


f. Các vitamin B6:
N
HOCH2

N

CH3
[O]

OH
C H 2O H

HOCH2

N

CH3

OH
CHO

NH 2OH

HOCH2

CH3

OH
CH N OH
L iA lH 4

N

NH 3

HOCH2

g.

CO CH 3
Cl

CO CH 2 N
Cl

CO CH 2 Br
Cl

H N

Br2

Cl

N

N

CH3

OH
C H 2N H 2

H O CH CH 2 N
Cl

N

NaBH 4

Cl

Cl

Cl
Cl
ClCH 2

Cl
Cl

Cl

Cl
CH O CH 2

Cl

CH 2
N
N

h.

CH 2OH

H

CHO

CH N NH

N

[O]

N

CH 2OH

NH NH2

CHO

CH N NH

12. Bổ sung quy trình tổng hợp dienoestrol:
CHO
KCN/alcol

CH 3O

CH C
OH O

OCH 3

Et Et
CH 3O

C C

OCH 3

HO OH

1) EtMgBr
2) H2O/H+

OCH 3
CrO3

CH 3O

C C
O O

2 H2O

OCH 3
CH 3O

OH
HBr

HO

OCH 3

H
N
N
N
N
H


13. Tổng hợp amiodaron:
CHO ClCH C C H
2
3 7 HO
O
OH

CHO

HBr

O

O
C

OCH 3

Cl C

C 4H 9

OCH3

O

C 4H 9

OH

O

C C 3H 7
O
NH2 NH2

O
C
O

H2O

O CH 2 C C 3H 7
O

I2/HO

O

O
C

I

C 4H 9

I

O

OH

ClCH 2CH 2N(C 2H 5)2

O
C 4H 9

HO

I

C
O

C 4H 9

O CH 2 CH 2 N (C 2 H 5 )2
I

ACID CARBOXYLIC VÀ DẪN CHẤT
1. Gọi tên:
CH 3 (CH 2)2 COOH

HOOC CH 2 COOH

Acid butyric
utanoic
HOOC (CH 2)2 COOH

Acid malonic
propandioic
HOOC CH CH COOH

Acid succinic
butandioic

Acid butendioic

ClCH 2 CH 2 COCl

Acid 2-chloropropanoylchlorid
Acid β-chloropropionylchlorid

Isopropylcyanid
Isobutyronitril
isobutanonitril

Acid glutaric
1,5(CH 3)2C CH CH 2 COOH

4-methyl-3-pentenoic

(CH 3)2CH COOC2H 5

CH 3 CH 2 CO N(CH 3)2

Ethylisobutyrat
ethylisobutano

N,N-dimethylpropionamid
N,N-dimethylpropanamid

O
(CH 3 )2 CH C N

HOOC (CH 2)3 COOH

O
O

Anhydrid phthalic

O
O
O

Anhydridsuccinic

Cl
C 3H 7

NH
CH 2

C CH 2CH 2COOH
O

Cl

Bufexamac
4(4’-propylphenyl)-4-oxo-butanoic

COOH

Diclofenac
Acid 2-[2’(2”,6”-dichlorophenylamino)]phenylacetic

CH COOH

C CH 2CH 2COOH

C

O

CH 3
O

Ketoprofe
n
Acid 2-methyl-2-(3’-benzoylphenyl)
acetic

Fenbuten
4-oxo-4-p-biphenylbutanoic
Cl

(CH 3)2CHCH 2

C CH 2CH 2COOH

CH COOH

O

CH 3

Acid butoxic
4(3’-chloro-4’-cyclohexylphenyl)-4-oxo-butanoic

Ibuprofen
Acid 2-methyl-2-(4’-isobutylphenyl)acetic

2. Viết công thức các hợp chất:

CH2 CH COOH

acid propenoic

O

acetylbromid

O

C

O

NHBr

N-bromopropionamid

C

C 2H 5

(CH 3CH 2CO)2O

Cl

Anhydrid propionic

O
N

CH 3

N-methyl-N-ethylacetamid

isobutyrylclorid

Acrylonitril

(CF3CO)2O

Br

Anhydrid trifluoroacetic

O

N-bromosuccinimid

(CH 3)2CH CH COOH
NH 2

Acid -aminoisovaleric
HO

CH 3 C N

Br

(CH 3)2CH C

CH 2 CH C N

CH 3CH 2C

CH 3 C

O

CH2 CH COOH
NH2

Acid -amino--(p-hydroxyphenyl)propionic

HS CH 2 CH COOH
NH 2

Acid -amino--thiolpropionic

(CH3)2CH CH2 COOH

Acid isovaleric


CH 3

CH 3
C CH 2 COOH

H
H

CH 3

COOH
OH
OH

CH 2 CH 2 CH CH 2 CH COOH
NH 2

COOH

CH 2 COOH
HO C

NH 2

Acid ,-diamino--hydroxycaproic

Acid mesotartric

Acid ,-dimethylbutyric

OH

CH 3 CH COOH

COOH

OH

CH 2 COOH

Acid lactic

Acid citric

3. Điều chế các acid từ alcol 4 carbon (hay ít hơn) và ester malonic hoặc phương pháp khác:
a. Acid valeric
PCl 5

CH 3 CH 2 CH 2 CH 2 OH

CH 3CH 2CH 2CH 2Cl
KCN

H2O/H

CH 3(CH 2)3COOH

+

CH 3CH 2CH 2CH 2CN

Hoặc:
CH 3CH 2CH 2OH

CH 2

COOC 2H 5
COOC 2H 5

PCl5

C 2H5O

CH 3CH 2CH 2Cl

CH

CH 3CH 2CH 2CH(COOC2H 5)2

COOC 2H 5

+

H2O/H

COOC 2H 5

CH 3CH 2CH 2CH(COOH)2
CO2

(CH 3)2CH OH PCl5

Acid valeric

PC l5

Hoặc:
CH2

o

CH 3CH 2CH 2CH 2COOH

b. Tương tự với acid isovaleric:
( C H 3 )2 C H C H 2 O H

t

KC N

H 2O/H

+

( C H 3 )2 C H C H 2 C O O H

COOC2H5
COOC2H5

+

H2O/H

C2H5O

t

o

CO2

(CH 3)2CHCH 2COOH

c. Acid -methylbutyric
CH 3 CH 2 CH OH
CH 3

PCl5

CH 3 CH 2 CH Cl
CH 3

KCN

CH 3 CH 2 CH CN
+

CH 3

H2O/H

CH 3CH 2CHCOOH
CH 3


d. Acid -methylbutyric
PCl5

CH 3 CH 2 CH OH

CH 3

KCN

CH 3 CH 2 CH Cl
CH 3

CH 3 CH 2 CH CN
CH 3
+

H2O/H

CH 3CH 2CHCOOH
CH 3

Acid -methylbutyric

e. Acid ,-dimethylbutyric
CH 3
CH 3 CH OH
CH 3

PCl 5

COOC 2H 5

CH 2

(CH 3)3C Cl

C 2H5O

COOC 2H 5

CH

COOC 2H 5
COOC 2H 5

(CH3)3C Cl

(CH 3)3CCH(COOC 2H 5)2
H2O/H

(CH 3)3CCH 2COOH

t

o

CO2

+

(CH 3)3CCH(COOH)2

4. Điều chế acid acrylic từ etylen
CH 2 CH 2

Cl2

200 600OC

CH 2 CH Cl

KCN

CH 2 CH CN

H2O/H

CH 3CH 2MgBr

CO2

+

CH 2 CH COOH

Hoặc
CH 2 CH 2
+

H2O/H

5.

HBr

CH 3CH 2Br

CH 3CH 2COOH

Mg/ete khan

Br2/P

CH 3CHBrCOOH

KOH/alcol

CH 3CH 2COOMgBr
CH 2 CH COOH


6.

7. Hoàn thành chuỗi phản ứng:
a.
C3H7COOH

Ca(OH)2

(C3H7COO)2Ca

to

C3H7 C C3H7 HCN
O

C3H7
C3H7

C

OH
CN
+

H2O/H

C 3H 7
C 3H 7

b.

CH3 CH CH2

Cl2

t cao
o

CH2 CH CH2

HBr

Cl

CH2 CH2 CH2
Cl

Br
KCN (1 mol)

Cl CH 2 CH 2 CH 2 COOH

2 H2O/H+

CH 2 CH 2 CH 2
Cl

NaOH dd

HOCH2CH2CH2COONa

+

H

CN

HOCH2CH2CH2COOH

C

OH
COOH

c.
Br2 / P

(CH 3)2CH COOH

CH 3
Br C COOH
CH 3

C 2H5OH/H2SO4

Cl

d.

COOH

CH 2OH

CH 2Cl

PCl 5

[H]

Br2

CH 3
O C COOC 2H 5

CH 3
Clofibrate

Cl

CH 2CN
KCN

Br CH CN
CH 2CN

ONa

CH 3
Br C COOC 2H 5
CH 3

C 6H 5 CH CN
+

H2O/H

C 6H6
AlCl 3

CH 3 CH CN

(C 6H 5)2CHCOOH

CH 3 CH COOH

+

1. NaNH2
2. CH3I

H2O/H

8. Điều chế acid pantothenic:
CH 2OH
H 3C C CHOH COOH

+

H 2N CH 2 CH 2 COOH

CH 3
CH 2OH
H 3C C CHOH CO NH CH 2 CH 2 COOH
CH 3

Acid pantothenic

H
CH 2OH
KCN
H 3C C CHO HCHO (CH 3)2C
CHO
CH 3

(CH 3)2C

+

H2O/H

CH 2OH
CHOH CN

CH 2OH
H 3C C CHOH COOH
CH 3

Acid 3,3-dimethyl-2,4-dihydroxybutyric
Cl CH 2 COOH

KCN

N C CH 2 COOH

[H]

H 2N CH 2 CH 2 COOH

-alanin


ACID CARBOXYLIC THƠM
1. Gọi tên:

COOH
Cl

COCl

NH 2

Br

Acid 2-cloro-4-aminobenzoic

COONa

p-bromobenzoylclorid

COOC2H 5

natribenzoat

COOH

COOH
OH

NH 2

COCH 3

Ethyl p-aminobenzoat

Acid o-hydroxybenzoic

p-acetylbenzoic
HO

COOH
COOH

Acid salicylic

COOH
OH

O
NH
O

OH

Acid phthalic

Acid 2,4,6-trihydroxybenzoic

Phthalimid

Acid gallic
N

3

O

4

H 2NO 2S

5

6

COOH
I

I
2

H 3C C NH

1 COOH

O

Acid 4-phenoxy-3-(pyrolidin-1-yl)-5-sulfonylaminobenzoic
CH 3O

CH COCH 3
2

CH 3O

3

O

Acid 3,5-diacetamido-2,4,6-triiodobenzoic

4

O

Acid 2-acetyl-2(3’,4’-dimethoxyphenyl)acetic
Acid 3-oxo-2-(3’,4’-dimethoxyphenyl)butanoic
O

NH C CH 3

Acid iotalamid

1

COOH

I

COOH

N
H

Acid 1,4-dihydro-4-oxo-quinolin-3-carboxylic

I

CHO

C NH CH (CHOH)3 CH 2OH
6 I

1
2

H 3C C N 3 4
O CH 3 I

5

NH C CH 3
O

(Metrizamid)

3-(N-methylacetamido)-5-acetamido-N-(1’-formyl2,3,4,5tetrahydroxy)penthyl-2,4,6-triiodobenzamid