Chapter 3 Carboxylic Acids Chm301

CHAPTER 3

Carboxylic Acids
• Carboxyl group, -COOH consist of a carbon
atom joined to an oxygen atom by a
double bond and to a hydroxyl group, OH,
by a single bond.

O
R C OH

• General formula: CnH2nCOOH

Naming of Carboxylic Acids
• Find the longest continuous carbon

chain containing the carboxyl group.
• Start numbering from the one that

closest to the carboxyl group, COOH.
• The ‘–e’ ending of the parent alkane is

replaced with ‘–oic acid’.
Example 1:
O
CH3CHCH2 C OH
CH3
3-methyl-butanoic acid
Example 2:
Cl O
CH3 C C OH
CH3
2-chloro-2-methyl-propanoic acid
Example 3:
O
CH3 C OH
4-methylcyclohexanoic acid
Example 4:
O
C OH
benzoic acid
Preparation of Carboxylic Acids
• Carboxylic acids come from alkenes by

the process called hydration.
• In between the conversion of alkenes to

carboxylic acids, alcohol and aldehydes
are formed by oxidation process.
Example:
H OH
CH2 CH2 H2 O/H+ KMnO4/H+
CH2 CH2
ethene heat
ethanol
H O O
H
KMnO 4/H + CH2 C OH
CH2 C H
heat ethanoic acid
ethanal
Preparation of Benzoic Acid by
Oxidation of Alkyl Benzene
CH3 CH2OH COOH
[O] [O]
Preparation of Carboxylic Acid by
Hydrolisis of Nitriles
R CH2 Cl + NaCN ethanol

reflux
R CH2 CN
nitrile
H2O/H+
R CH2 COOH
Carboxylation of Grignard Reagents
O
[1] CO2
R MgX + R C OH
[2] H3O
• Grignard reagents react with CO2 to give

carboxylic acids after protonation with
aqueous acid.
Grignard Synthesis
(CH3CH2)2O
R X + Mg R Mg X
Grignard reagents
(CH3CH2)2O
H3C Br + Mg H3C Mg Br
Methylmagnesium
bromide
Example:
Cl MgCl COOH
Mg CO2/H3O+
[1] [2]
phenylmagnesium
chloride
1) Formation of Grignard Reagent

2) Reaction with CO2
Reactions of
Carboxylic
Acids
Formation of Salt
• Carboxylic acids are weak acids. They turn

blue litmus to red.
• They undergo neutralization reactions

with base to form salts of carboxylic acid
and water.
Example:
RCOOH + NaOH RCOO- Na+ + H2O

carboxylic acid sodium sodium carboxylate
hydroxide
CH3COOH + NaOH CH3COO- Na+ + H2O

ethanoic acid sodium ethanoate
Reduction to Alcohols
• Carboxylic acids are reduced to primary

alcohols when it is reacts with lithium
aluminum hydride (LiAlH4) in dry ether.
• The reaction doesn’t work with other

reducing agent.
General reaction:
O H
R C OH LiAlH 4 in ether
R C OH
carboxylic acid
H
primary alcohol
Example:
O H
CH3 C OH LiAlH 4 in ether CH3 C OH
ethanoic acid
H
ethanol
Formation of Acyl Chlorides
• Carboxylic acids canNOT be converted to
acid chlorides by using Cl- as a nucleophile
because Cl- is a weaker base than the
departing leaving group –OH.
• Carboxylic acids react with thionyl chloride,

SOCl2 at room temperature to form acyl
chlorides.
General reaction:
O
room temp.
R C OH + SOCl2
carboxylic acid
O
R C Cl
acyl chloride
Formation of Esters
• Carboxylic acids is heated with alcohols

in the presence of acid catalyst to form
an ester.
• This reaction is called Fisher

esterification.
General reaction:
O
conc. H2SO4
R C OH + HO R'
heat
carboxylic acid alcohol
O
R C O R' + H2O
ester
Example of Esterification
O
conc. H2SO4
CH3 C OH + HO CH2CH3 heat
ethanoic acid ethanol
O
CH3 C O CH2CH3 + H2O
ethylethanoate
Formation of Amides
• Two-step of reactions. Step 1: The
preparation of ammonium salt. Carboxylic
acid reacts with ammonia to produce an
ammonium salt of carboxylic acid.
• Step 2: Formation of amide. The

ammonium salts of carboxylic acid is
heated to form amide.
General reaction:
O NH3
O
R C OH
(ammonia)
R C O- NH4+
carboxylic acid ammonium salt
heat
O
R C NH2 + H2O
amide
Example:
O
C - +
CH3 O NH4 heat
ammonium ethanoate
O
CH3 C NH2 + H2O
ethanamide
Formation of Acid Anhydrides
• Acid anhydride is prepared in the

laboratory from reaction of carboxylic
acid with acyl chloride in the presence of
pyridine.
General reaction:
N
O O
R C OH + Cl C R' pyridine
carboxylic acid acyl chloride
O O
R C O C R' + HCl
acid anhydride
Example:
N
O O
pyridine
CH3 C OH + Cl C CH3
ethanoic acid ethanoyl chloride
O O
CH3 C O C CH3 + HCl

ethanoic anhydride

Chapter 3 Carboxylic Acids Chm301

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CHAPTER 3

• General formula: CnH2nCOOH

• Find the longest continuous carbon

• Start numbering from the one that

• The ‘–e’ ending of the parent alkane is

• Carboxylic acids come from alkenes by

• In between the conversion of alkenes to

CH3 CH2OH COOH

R CH2 Cl + NaCN ethanol

• Grignard reagents react with CO2 to give

1) Formation of Grignard Reagent

• Carboxylic acids are weak acids. They turn

• They undergo neutralization reactions

RCOOH + NaOH RCOO- Na+ + H2O

CH3COOH + NaOH CH3COO- Na+ + H2O

• Carboxylic acids are reduced to primary

• The reaction doesn’t work with other

• Carboxylic acids react with thionyl chloride,

• Carboxylic acids is heated with alcohols

• This reaction is called Fisher

• Step 2: Formation of amide. The

• Acid anhydride is prepared in the

CH3 C O C CH3 + HCl

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