1. The document provides the names and chemical structures of various carboxylic acids and related compounds. 2. Steps are given for synthesizing carboxylic acids from alcohols, alkyl halides, nitriles, and other precursors through reactions such as halogenation, nucleophilic substitution, hydrolysis, and oxidation. 3. Specific syntheses are outlined for derivatives of toluene, benzoic acid, p-toluidine, and other aromatic compounds. Reactions include halogenation, nitrile formation, hydrolysis, acetylation, and oxidation.

1. 1
ACID CARBOXYLIC BEÙO VAØ DAÃN CHAÁT

2. 2
1.Goïi teân
CH3 (CH2)2 COOH CH2 COOHHOOC HOOC (CH2)3 COOH
Acid butyric
butanoic
Acid malonic
propandioic
Acid glutaric
1,5-pentandioic
(CH2)2HOOC COOH COOHHOOC CHCH CH2(CH3)2C CH COOH
CH2ClCH2 COCl (CH3)2CH COOC2H5 CH3 CH2 CO N(CH3)2
(CH3)2CH C N O
O
O
O
O
O
Acid succinic
butandioic
Acid butendioic 4-methyl-3-pentenoic
Acid 2-chloropropanoylchlorid
Acid β-chloropropionylchlorid
Ethylisobutyrat
ethylisobutanoat
N,N-dimethylpropionamid
N,N-dimethylpropanamid
Isopropylcyanid
Isobutyronitril
isobutanonitril
Anhydrid phthalic Anhydridsuccinic

3. 3
COOH
NH
CH2 Cl
Cl
C
O
CH2CH2COOH
C3H7 C
O
CH2CH2COOH
Acid 2-[2’(2”,6”-dichlorophenylamino)]phenylacetic
Diclofenac
4-oxo-4-p-biphenylbutanoic
Fenbuten
4(4’-propylphenyl)-4-oxo-butanoic
Bufexamac

4. 4
(CH3)2CHCH2 CH
CH3
COOH
Acid 2-methyl-2-(4’-isobutylphenyl)acetic
Acid 2-methyl-2-(3’-benzoylphenyl) acetic
C
O
CH
CH3
COOH
Ibuprofen
Ketoprofen
Cl
C
O
CH2CH2COOH
4(3’-chloro-4’-cyclohexylphenyl)-4-oxo-butanoic
Acid butoxic

5. 5
2. Vieát coâng thöùc caùc hôïp chaát
CH2 CH COOH CH3
O
Br
C
CH3 C
O
N
CH3
C2H5
CH2 CH C N
acid propenoic acetylbromid N-methyl-N-ethylacetamid
Acrylonitril
C(CH3)2CH
O
Cl
(CH3CH2CO)2O
CH3CH2C
O
NHBr
O
O
C
N
C
Br
isobutyrylclorid Anhydrid propionic
N-bromopropionamid
N-bromosuccinimid
(CF3CO)2O
CH COOH(CH3)2CH
NH2
CH2 CH COOHHS
NH2
Anhydrid trifluoroacetic
Acid -aminoisovaleric Acid -amino--thiolpropionic

6. 6
CH2CH3 C
CH3
CH3
COOH
COOH
COOH
H
H
OH
OH
CH2CH2
NH2
CH CH2 CH
NH2
COOH
OH
Acid ,-dimethylbutyric Acid mesotartric
Acid ,-diamino--hydroxycaproic
CH2
CHO
COOH
CH2
COOH
COOH
CH3 COOHCH
OH
Acid citric
Acid lactic
CH2HO CH COOH
NH2
CH2 COOH(CH3)2CH
Acid -amino--(p-hydroxyphenyl)propionic Acid isovaleric

7. 7
3. Ñieàu cheá caùc acid töø alcol 4 carbon (hay ít hôn) vaø ester malonic hoaëc pp
khaùc:
CH2CH3 CH2 OHCH2
PCl5 CH3CH2CH2CH2Cl
KCN
CH3CH2CH2CH2CN
H2O/H
+
CH3(CH2)3COOH
CH3CH2CH2OH CH3CH2CH2Cl
PCl5
CH2 CH
COOC2H5
COOC2H5
C2H5O
COOC2H5
COOC2H5
CH3CH2CH2CH(COOC2H5)2
H2O/H
+
CH3CH2CH2CH(COOH)2
t
o
CH3CH2CH2CH2COOH
CO2
a. Acid valeric
Acid valeric
Hoaëc:

8. 8
b. Töông töï vôùi acid isovaleric CH2 COOH(CH3)2CH
(CH3)2CH OHCH2
KCN H2O/H
+
PCl5 CH2 COOH(CH3)2CH
(CH3)2CH OH
H2O/H
+
PCl5
C2H5O
t
oCH2
COOC2H5
COOC2H5
CO2
(CH3)2CHCH2COOH
c.Acid -methylbutyric
CH3
CH3 CH2
H2O/H
+
PCl5CH3 CH2 CH OH CH CN
CH3
KCNCl CH3 CH2 CH
CH3
CH3CH2CHCOOH
CH3
Hoaëc:
Acid -methylbutyric

9. 9
d.
CH3OH
I2 / P
CH3I
(CH3)2CH
CH3
PCl5
CH ClCH3 CH2 OH CH2
C2H5O
CH
COOC2H5
COOC2H5
CH2
COOC2H5
COOC2H5
(CH3)2CH ClCH2 (CH3)2CHCH2CH(COOC2H5)2
CH3
CH3IC2H5O
(CH3)2CHCH2C(COOC2H5) (CH3)2CHCH2C(COOC2H5)2
H2O/H
+
CH3CH3
t
o
CO2
(CH3)2CHCH2C(COOH)2 (CH3)2CHCH2CHCOOH
Acid 2,4-dimethylpentanoic

10. 10
OH PCl5
CH3
CH3 CH
CH3
(CH3)3C Cl
CH
COOC2H5
COOC2H5
CH2
COOC2H5
COOC2H5
C2H5O (CH3)3C Cl
(CH3)3CCH(COOC2H5)2
H2O/H
+
(CH3)3CCH(COOH)2(CH3)3CCH2COOH t
o
CO2
e.
Acid ,-dimethylbutyric

11. 11
4. Ñieàu cheá acid acrylic töø etylen
COOHKCNCH2 CH2
Cl2
200 600O
C
CH2 CH2CHCH CH2 CHCl CN
H2O/H
+
CH2 CH2
HBr CH3CH2Br Mg/ete khan
CH3CH2MgBr
CO2
CH3CH2COOMgBr
H2O/H
+
CH3CH2COOH
Br2/P
CH3CHBrCOOH
KOH/alcol
COOHCH2 CH
hoaëc:

12. 12

13. 13

14. 14
7. Hoaøn thaønh chuoãi p/öù:
C3H7COOH
Ca(OH)2 C3H7 C3H7C
O
(C3H7COO)2Ca to
HCN
OH
CN
C3H7
C3H7
C
COOH
OHC3H7
C3H7
C
H2O/H
+
a.
b.
CH2CHCH2 CH2CHCH3
Cl2
to
cao
Cl
HBr
Br
CH2CH2CH2
Cl
CH2
CN
H2O/H
+
CH2 COOHCH2Cl
KCN(1 mol)
CH2CH2CH2
Cl
2
NaOH dd
HOCH2CH2CH2COONa H
+
HOCH2CH2CH2COOH

15. 15
c.
(CH3)2CH COOH
Br2 / P
C
CH3
CH3
Br COOH
C2H5OH/H2SO4
Br C
CH3
CH3
COOC2H5
Cl ONa
Cl O C
CH3
CH3
COOC2H5
Clofibrate
d. COOH CH2OH
[H] PCl5 KCN
CH2Cl CH2CN
CH2CN
Br2
CH CNBr
C6H6
AlCl3
C6H5 CH CN
H2O/H
+
(C6H5)2CHCOOH
NaNH2
CH3I
1.
2.
CHCH3 CN CH COOH
H2O/H
+
CH3

16. 16
8. Ñieàu cheá acid pantothenic
C KCNH3C
H
CH3
CHO HCHO (CH3)2C
CH2OH
CHO
(CH3)2C
CH2OH
CHOH CN
H2O/H
+
CH2OH
CHOH COOHC
CH3
H3C
Acid 3,3-dimethyl-2,4-dihydroxybutyric
COOHCOOH COOH[H]
Cl CH2 CH2CH2 CH2
KCN N C H2N
-alanin
COOHH3C
CH2OH
CHOH CH2 CH2C
CH2OH
CHOH COOHC
CH3
H3C COOHCH2 CH2H2N+
CH3
CO NH Acid pantothenic

17. 17
ACID CARBOXYLIC THÔM

18. 18
1. Goïi teân
COOH
Cl
NH2
COCl
Br
COONa
COOC2H5
NH2
COOH
COCH3
Acid 2-cloro-4-aminobenzoic p-bromobenzoylclorid natribenzoat
Ethyl p-aminobenzoat p-acetylbenzoic
COOH
OH
COOH
COOH
HO
OH
OH
COOH
Acid o-hydroxybenzoic
Acid salicylic
Acid phthalic Acid 2,4,6-trihydroxybenzoic
Acid gallic
NH
O
O
Phthalimid

19. 19
COOH
O
H2NO2S
N
1
2
3
6
4
5
Acid 4-phenoxy-3-(pyrolidin-1-yl)-5-sulfonylaminobenzoic
1
2 3 4
CH3O
CH3O
CH COCH3
COOH
Acid 2-acetyl-2(3’,4’-dimethoxyphenyl)acetic
Acid 3-oxo-2-(3’,4’-dimethoxyphenyl)butanoic
N
H
COOH
O
Acid 1,4-dihydro-4-oxo-quinolin-3-carboxylic

20. 20
COOH
I
I I
NH CH3NHC
O
H3C C
O
Acid 3,5-diacetamido-2,4,6-triiodobenzoic
CH3
1
2
3
6
4
5
O
I
I I
NH CH3
NH
C
O
H3C C
O
N
C CH
CHO
(CHOH)3 CH2OH
3-(N-methylacetamido)-5-acetamido-N-(1’-formyl-
2,3,4,5tetrahydroxy)penthyl-2,4,6-triiodobenzamid
(Metrizamid)
Acid iotalamid

21. 21
2. Vieát coâng thöùc
O
O
O
COOH
CH3
COOH
COOH
C N
Anhydrid phthalic Acid m-toluic Acid terephthalic Benzonitril
Cl COONH4
COOCH2C6H5
H3C CH2CH2COOH C
O
Br
Amoni p-chlorobenzoat benzylbenzoat
Acid 3-(p-tolyl)propionic benzoylbromid

22. 22
3. Töø toluen ñieàu cheá
CH3
KMnO4/H
+
COOH
a.
b.
c.
Cl
COOHCH3
Cl2/Fe
CH3
KMnO4/H
+
Cl
CH3
Cl2 / aùs
CH2Cl
KCN
CH2CN
H2O/H
+
CH2COOH

23. 23
e.
f.
COOH
H2O/H
+
CH3CH3
Br2/Fe
Br
Mg/ete khan
MgBr
CO2
COOMgBr
CH3CH3 CH3
COOH
Cl2/FeKMnO4/H
+
Cl
CH3 COOH
d.
CH3CH3
Cl2 / aùs
CH2Cl
KCN
CH2CN
H2O/H
+
CH2COOH
Br2/Fe
Br Br BrBr
3.

24. 24
4. Töø benzen ñieàu cheá

25. 25
5. Töø p-acetylbenzen ñ/c
Cl2 / aùs
COCH3
CH2CH3
I2 NaOH+
COOH
H2O/H
+
CH2CH3 CH2CH3
COONa
diacetylbenzen
Acid p-ethylbenzoic
NaOH dd
COCH3 COCH3 COCH3
COCH3CHClCH3 CHOHCH3
[O]

26. 26
6. Thöïc hieän p/öù
Acid acetylsalicylic
(aspirin)
CO2NaOH dd
OH OHONa
t
o
p,
COOH
H
+COONa
OH
CH3COCl
pyridin
OCOCH3
COOH
COOH
KMnO4/H
+
CH3 CH3 COOH
CHO CH(OC2H5)2
C2H5OH2
CHOCH(OC2H5)2
H2O
a.
b.
hoaëc
H2O/H
+
CHO
CH3
CHO
CCl3
Cl2/aùs3
COOH
CHO
p-carboxylbenzaldehyd

27. 27
7. Töø p-toluidin ñ/c
KMnO4/H
+
CH3CH3 COOH
H2O
H2N
H2N
(CH3CO)2O
CH3CONH CH3CONH
C2H5OH/H
+
COOC2H5COOC2H5 CH3CONH
anesthesin
KMnO4/H
+
CH3CH3 COOH
H2O
H2N
(CH3CO)2O
CH3CONH CH3CONH
HOCH2CH2N(C2H5)2
CH3CONH COOCH2CH2N(C2H5)2
COOCH2CH2N(C2H5)2H2N
Novocain

28. 28
CH3CH3CO
C
O
O
HO
OHCO
O C
O
O
O
O
O
C
8. Giaûi thích aspirin thuûy phaân nhanh gaáp 4-8 laàn caùc este thoâng thöôøng
Caáu truùc anhydrid
Anhydrid thuûy phaân nhanh hôn este

29. 29
9. Hoaøn thaønh caùc chuyeån hoùa
CH3
Br
Mg
ether khan
CO2
MgBr
CH3 CH3
COOMgBr
HCl
CH3
COOH
[O]
COOH
COOH
NH3NH O
CC
O
OO
O
C C
a.

30. 30
b.
CH3
H2SO4
ñp para
ñp ortho
CH3 CH3 CH3
COOH
NaOH NaCN
SO3H SO3Na CN
CH3 CH3
H2O/H
+
2 C2H5OH
COOC2H5
[O]
COOH
COOH
CH3
SO3H
COOH
SO3H
NaOH NaOH
300O
C ONa
CH3COCl
OCOCH3
9.

31. 31
c.
COOHCOOH
O
H2SO4
Br
+
HS
R
S
R R
HO
H2O
C
S
RC
S
BrMgO CH2 (CH2)2 NN R
R (CH2)2 CH2MgBrNN
RC
S
CH2 (CH2)2 NN R
H2O
HO
9.

32. 32
CH2Cl
C6H5CHO
CH2MgCl
Mg
ether khan
CH
OMgBr
CH2C6H5
H2O/H
+
CH CH2C6H5
OH
H2SO4
C6H5 CH CH C6H5 C6H5 CH
Br
CH
Br
C6H5
Br2
KOH/alcol C6H5 C C C6H5
d.
d.
9.

33. 33
O
H2O
2O
C
O
O
C C
O
C
OHHO
C6H5OH
O
NaOH
C
HO
COONa
pH = 9
e.
f.
Phenolphtalein Maøu hoàng
C6H5COOH
PCl5
C6H5COCl
NH3
C6H5CONH2
P2O5
C6H5C N
H2/Ni
C6H5CH2NH2
Cl C
O
ClC6H5CH2NH NHCH2C6H5C
O
9.

34. 34
10. Hoaøn thaønh chuoãi phaûn öùng
COOHHO
OH
CH3I2
COOHCH3O
OCH3
CH3O
OCH3
COCl
SOCl2
COCH3
OCH3
CH3O
CH3ZnBr
OCH3
CH3O COCH2Br
(CH3)3C NH2Br2
CH3O
OCH3
COCH2NH C(CH3)3
NaBH4
CH3O
OCH3
CH CH2 NH C(CH3)3
OH
H2O/H
+
2
HO
OH
CH CH2 NH C(CH3)3
OH
a.
terbutalin

35. 35
b.
COOHCH3
ClSO2OH
SO2Cl
CH3
(C3H7)2NH
SO2 N(C3H7)2
CH3
KMnO4
SO2 N
C3H7
C3H7
COOHCH3 COOH
ClSO2OHKMnO4
ClCl ClCl ClCl
ClO2S
NH3
COOH
ClCl
H2N SO2 COOH
Cl
H2N SO2
O
NH
CH2O
NH2
Furosemid
Probenecid
c.
10.

36. 36
d.
CH3
HNO3/H
+
O2N CH3
KMnO4 O2N COOH
O2N
O
C Cl
SO2Cl
H2NCH2CH2N(C2H5)2
O2N C NHCH2CH2N(C2H5)2
O
H2N
[H]
C NHCH2CH2N(C2H5)2
O
Procainamid

37. 37
e.
O
C
NH C
O
CH3
COOH
H2N
H3C NH
H3C
NH C
O
CH3
H3C
O
C CH3
C
OH
N
H
N
Methaqualon
H3C
O
CH3
H2O
N
N
10.

38. 38
COOH
C
COOH
OO
C
C
O
O
ClCl
Cl
O
ClSO2OH
NH4OH
1.
2.
SO2NH2
C
f.
O
SO2Cl
NH4OH
1.
2.
O
Cl
SO2NH2
C
C NH2
10.