CHAPTER 17

CARBOXYLIC ACIDS
17.1 Introduction
17.2 Nomenclature
17.3 Physical Properties
17.4 Preparation
17.5 Chemical Properties
 CARBOXYLIC ACID COMPOUNDS OVERVIEW
17.1 INTRODUCTION 17.2 NOMENCLATURE
General general formula of aliphatic and aromatic Draw and name carboxyl compounds
carboxylic acid. according IUPAC nomenclature
give common name for C1-C5
17.4 PREPARATION OF
ACIDS
1. Preparation of acid 18.0 CARBOXYLIC ACID
compounds via: and its DERIVATIES
Oxidation of alkylbenzene, R-OH,
aldehyde
hydrolysis of nitrile compound 17.5 CHEMICAL PROPERTIES OF
carbonation of Grignard reagents. CARBOXYLIC ACID COMPOUNDS
1.Explanation the chemical properties with
reference to;
17.3 PHYSICAL PROPERTIES OF ACIDS neutralisation with base
reaction with metal, Na, Mg or Ca
1. explain the resonance or
reduction with LiAlH4 followed by hyrolysis
inductive effect when discuss
acyl chloride formation
acidity of acid
anhydride formation
i) compare to alcohols and phenol.
esterification
ii) halogenated carboxylic acid based
amide formation
on number of halogens or position
2. Explain the reducing properties of methanoic
of halogen
acid with;
2. Boiling point acid higher compare to
KMnO4/H+
alcohol and other compounds.
Tollens reagent
3. Solubility in water: acid more soluble
3. Uses of carboxylis acid and its derivaties
compare to alcohol and other compounds
solubility acid in organic solvent
 Learning outcomes
At the end of the lesson, you should be able to:

a) Write the general formula of carboxylic acids.

b) Draw the structures and write the IUPAC name for
carboxyl compounds (parent chain C10).
c) Write the common names for carboxylic acids with
parent chain C5

3
 Introduction

If R = H
Youll get H COOH

O
||
H C OH

methanoic acid

4
 Introduction

O
||
Compounds with carboxyl group : - C OH
General formula :
Carbonyl + hydroxyl

O
||
R C OH

can be written as : R COOH

R = H or alkyl or aryl 5
 Introduction

If R = alkyl
Youll get CH3 COOH

O
||
CH3 C OH

ethanoic acid

6
 Introduction

If R = alkyl

O
||
CH3 CH2 C OH

propanoic acid

7
 Introduction

If R = aryl
Youll get C6H5 COOH -COOH

O
||
C OH

benzoic acid

8
 Nomenclature
Common Names You should know

Structural Formula IUPAC Name Common Name

HCOOH Methanoic acid Formic acid

CH3COOH Ethanoic acid Acetic acid

CH3CH2COOH Propanoic acid Propionic acid
CH3(CH2)2COOH Butanoic acid Butyric acid

CH3(CH2)3COOH Pentanoic acid Valeric acid

9
 Nomenclature
Common Names
Number Common Common
IUPAC name Chemical formula
of C name location or use
6 Caproic acid Hexanoic acid CH3(CH2)4COOH Goat fat
7 Enanthic acid Heptanoic acid CH3(CH2)5COOH
Coconuts and
8 Caprylic acid Octanoic acid CH3(CH2)6COOH
breast milk
Pelargonic
9 Nonanoic acid CH3(CH2)7COOH Pelargonium
acid
10 Capric acid Decanoic acid CH3(CH2)8COOH ???
Coconut oil and
12 Lauric acid Dodecanoic acid CH3(CH2)10COOH
hand wash soaps.
Tetradecanoic
14 Myristic acid CH3(CH2)12COOH Nutmeg
acid
16 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH Palm oil
Chocolate, waxes,
18 Stearic acid Octadecanoic acid CH3(CH2)16COOH
soaps, and oils
10
20 Arachidic acid Icosanoic acid CH3(CH2)18COOH Peanut oil
 Nomenclature
TAKE NOTE
The longest chain must include the carboxyl group.
The carboxyl group always at the end of the chain,
therefore the carbon of the carboxyl group is always
numbered as C 1.
When there are two carboxyl groups present - COOH
are at both ends.
Name the compound as alkane, drop e in alkane and
add oic acid
example : methane methanoic acid

11
 Nomenclature
If a compound contains a carboxyl group and other
functional group(s), the priority is given to the carboxylic
acid as the parent name.

CH3 O
5 4 3| 2 ||1
CH3CHCHCH2COH
|
Br
4-bromo- 3-methylpentanoic acid
6
CH3 O
| ||
HOCHCH2CH2CH2COH
5 4 3 2 1
5-hydroxylhexanoic acid 12
 Nomenclature

O CH3
|| |
HOCCH2CH=CHCHCH3
1 2 3 4 5 6

5-methyl-3-hexenoic acid

13
 Nomenclature

When two COOH groups are present, the compound will

be named as alkanedioic acid.

O O
|| ||
HOCCH2CH2CH2COH

Pentanedioic acid

14
 Nomenclature

O CH3 O
|| | ||
HOCCH2CHCH2CH2COH
1 2 3 4 5 6

3-methylhexanedioic acid

H CH2COOH
2 1
C4 = C 3

HOOC-CH2 H
6 5

trans- 3-hexenedioic acid 15

 Nomenclature
If R is an aryl group, the parent name is benzoic acid.
The C atom attached to COOH is numbered as C1.
The C at the -COOH group is not numbered !

COOH Cl
6
5
1
Br 1
2 4 COOH
2
3

Cl
2-bromobenzoic acid 2,5-dichlorobenzoic acid
16
 Nomenclature

Two COOH group present = aromatic dicarboxylic acid

Named as . 1, . -benzenedicarboxylic acid.

COOH
1
2

3
COOH
1,3-benzenedicarboxylic acid
17
 Nomenclature

HOOC
4 3

2
Cl
1

COOH

2-chloro-1,4-benzenedicarboxylic acid
18
 Nomenclature
A cyclic carboxylic acid is named as
cycloalkanecarboxylic acid.
The C atom attached to the COOH is numbered as C 1.

1
COOH

cyclopentanecarboxylic acid
19
 Nomenclature

CH3
3 2

4 1
Br COOH

4-bromo-2-methylcyclohexanecarboxylic acid

20
 Nomenclature
Try this
2 1
a) H2NCHCOOH
3CH2
2amino3phenylpropanoic acid

b) OH

4
3
2 3hydroxybenzoic acid
1 or
5
6 COOH mhydroxybenzoic acid
21
 Nomenclature
Try this
O
6 5 4 3 2 1
c) CH3CH2CCHCH2COH

CH3
4methyl3hexenoic acid

Cl
4 2
5 3 1
d)
COOH

2chloro3methylpentanoic acid
22
 Nomenclature
Try this

CH3 O
CH C
H3C OH

NH2

23