1.1 Common name a. F F 1.2 IUPAC name

O
-C-OH
b. !"#
$$
%
Carboxyl group
1.1 Common name
a. HCOOH
Formic acid
Acetic acid
CH3COOH
CH3CH2COOH
Propionic acid
CH3(CH2)2COOH Butylic acid
δ γ β α
-C-C-C-C-COOH
CH3(CH2)3COOH Valeric acid
CH3(CH2)4COOH Caproic acid
CH3(CH2)6COOH Caprylic acid
CH3(CH2)10COOH Lauric acid
CH3(CH2)12COOH Myristic acid
CH3(CH2)14COOH Palmitic acid
CH3(CH2)16COOH Stearic acid
α
β
γ
δ
ε
ζ
η
τ
υ
ξ ο π ρ σ
CH3
θ
φ
κ λ
χ
ψ
µ
ν
ω
CH3CH2CH-CHCOOH
CH3 CH3
CH3CH2CHCOOH
α-Methylbutyric acid
ι
α,β-dimethylvaleric acid
1
2
1.2 IUPAC name
CH3CHCOOH
OH
a. è ÍßÌ«´áð×è Õ Ëá×Ã alkane é ¿’¿Û¾ “ e” #$'"$
-oic acid
("$
C
C C )*+,-."# 1 /
CH2CH2CHCOOH
Cl
CH3
α-hydroxypropionic acid γ-chloro-α-methylbutyric acid
(Lactic acid)
CH2CH2CH2COOH
γ-phenylbutyric acid
5 4 3 2 1
-C - C - C - C - COOH
CH3CH2COOH
Propanoic acid
CH3
Cl
CHCH2COOH
CH2=CHCOOH
Acrylic acid
3
CH3CH=CHCOOH
2-Butenoic acid
CH3CH2CHCOOH
CH3
4
3-(4’-chlorophenyl)butanoic acid 2-methylbutanoic acid
1.2 IUPAC name
b. #'"$
“ic
ic acid’
ate”
acid #$“-ate
ate
(CH3COO)2Ca
Calcium acetate
Calcium ethanoate
CH2 - CH - COOK
Br
Br
O
H-O
C-R
R-C
O-H
Potassium
-2,3-dibromopropanoate
HCOONH4
Ammonium formate
Ammonium methanoate
/ 1
1. (!
#(!
$
2.
O
"
aliphatic carboxylic acid C 5 !" ! # !$ C %&'
aromatic carboxylic acid COONa
Sodium benzoate
5
-2 1. Oxidation of primary alcohol
6
-2 2. Oxidation of alkylbenzene
R-CH2OH + KMnO4/OH- --------> R-COOH
KMnO4/OHK2Cr2O7/H+
R
CH3
CH3
KMnO4/OHCH3CH2CHCH2OH
CH3CH2CHCOOH
CH3
Br
COOH
KMnO4/OHK2Cr2O7/H+
COOH
Br
CH3
CH2CHCH3
KMnO4/OHK2Cr2O7/H+
7
NO2
?
8
-2 3. Carbonation of Grignard reagent
Mg
R-X
(or Ar-X)
R-MgX
CO2
R-COOMgX
O
Mg
CH3Cl
Br
CH3 - MgCl
C=O
MgBr
Mg
-2 4. Hydrolysis of nitrile compound
CO2
H+
O
CH3COMgCl
COOMgBr
H+
CHCH3
CHCH3
CHCH3
CH3
CH3
CH3
R-C N
or
C N
R-COOH
(or Ar-COOH)
+
H2O
R-COOH
or
COOH
H+
O
H+
CH3COH
CH3CH2Br+NaCN-->CH3CH2CN+H2O/H+--->
Br+NaCN--->CH
---> CH3CH2COOH
COOH
?
CHCH3
CH3
COOH
CN
reflux/H2SO4
NO2
NO2
9
10
-2
', -2
', 1. Acidity : salt formation
2. Conversion into functional derivatives
RCOOH
O
RCOO- + H+
O
R-C-OH
CH3COOH + Zn -----> (CH3COO-)2Zn
RC-OH
NaHCO3
R-C-Z
O
COONa
COOH
+ NH3
+ CO2 + H2O
11
+
SOCl2
PCl3
PCl5
(Z = -Cl, -OR, -NH2, -OOCR)
[ ]
O
RCCl
Acid chloride
12
-2
', -2
', 2. Conversion into functional derivatives
2. Conversion into functional derivatives
O
RC-OH + RO-H
O
O
H+
CH2COOH
SOCl2
RC-OR
ESTER
O
SOCl2
R-C-OH
O
2R-C-OH
O
RC-Cl
NH3
O
RC-NH2
O
O
O
RC-O- CR
H+
CH2CNH2
CH2COCl
NH3
O
2CH3COH + H+
O
CH3C-O-CCH3 + H2O
Acetic anhydride
Acid anhydride
13
-2
', -2
', 4. Substitution in alkyl or aryl group
a. Alpha-halogen of aliphatic acids
3. Reduction
R-COOH
LiAlH4
R-CH2OH
1o alc.
RCHCOOH
LiAlH4
CH3
X2/P
H
CH2OH
COOH
14
CH3
CH3CHCH2COOH
CH3
RCHCOOH + HX
X
Br2/P
CH3
CH3CHCHCOOH
Br
15
16
-2
', 4. Substitution in alkyl or aryl group
b. Ring substitution in aromatic acid
COOH
Problem :
1. n-Propyl alcohol + ? ----------> n-Butylic acid
2. Bromobenzene + ? ------------> Benzoic acid
3.
O
COOH
HNO3/H2SO4
heat
CH3CCH2CH2CH3
NO2
4.
CH3
CH3CH2CH2COOH
CH2COOH
?
17
18

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