Chapter 20: Carboxylic

Acids and Nitriles

20.1
Rank the following molecules in acidity from
least acidic to most acidic.
Cl O O O
Cl
OH OH OH
Cl
A B C

1. A< C< B
2. B<A<C
3. C<B<A
4. B<C<A
5. C<A<B
 20.1 answer
Rank the following molecules in acidity from
least acidic to most acidic.
Cl O O O
Cl
OH OH OH
Cl
A B C

1. A< C< B
2. B<A<C
3. C<B<A
4. B<C<A
5. C<A<B
20.2

p-Chlorobenzoic acid is more acidic

than p-methylbenzoic acid .
O O
OH OH
Cl

1. True
2. False
20.2 answer
p-Chlorobenzoic acid is more acidic
than p-methylbenzoic acid .
O O
OH OH
Cl

1. True
2. False
20.3 1. CO2
CH3CH2MgBr
+
2. H

(a)
H3C COOH (d)

COBr
(b)
COOH (e)

COBr
(c)
COOH
20.3 answer
(a)
H3C COOH (d)

COBr
(b)
COOH (e)

COBr
(c)
COOH

Grignard reagents add to carbon dioxide to form a

salt of a carboxylic acid. Hydrolysis forms a
carboxylic acid.
 H2SO4
21.4 CH3CH2C N
heat

O
(a) CH2NH2 (b)
NH2

(c)
COOH (d)
COOH
21.4 answer

O
(a) CH2NH2 (b)
NH2

(c)
COOH (d)
COOH
20.5
O SOCl2
or POCl3

NH2

CH2NH2
(a) (b)
COOH

O
(c) CN (d)
H
 20.5 answer

CH2NH2
(a) (b)
COOH

O
(c) CN (d)
H
 1. CH3CH2CH2MgCl
20.6 CH3CH2C N
+
2. H3O
O
O
(a) (b)

O OH

(c) (d)
 20.6 answer
O
O
(a) (b)

O OH

(c) (d)

The propyl group adds to the nitrile.

 What sequence of reagents will accomplish
20.7 the following transformation?
O

OH
1.
HBr Mg CO2 H3O+

Et2O

2.
Br2 Mg CO2 H3O+

h Et2O

3.
Br2 CO2 H3O+

h

4.
HBr CO2 H3O+

5.
Mg CO2 H3O+

Et2O
20.7 answer
O

OH

1.
HBr Mg CO2 H3O+

Et2O

2.
Br2 Mg CO2 H3O+

h Et2O

3.
Br2 CO2 H3O+

h

4.
HBr CO2 H3O+

5.
Mg CO2 H3O+

Et2O
20.8 Which of the following reactions cannot be
performed with a nitrile?
1.
O
CN
OH

2.
O
CN

3.
CN NH2

4.
CN Br
 20.8 answer

1.
H3O+ O
CN
OH

2.
1.CH3MgBr O
CN
2. H3O+

3.
LiAlH4
CN NH2

4.
CN Br
 Determine the product of the following
20.9 sequence of reactions.
Br NaCN H3O+

DMSO heat

1. 2.
O NH2

NH2 O

3. 4.
OH O

O OH

5.
OH

CN
 20.9 answer

Br NaCN H3O+

DMSO heat

1. 2.
O NH2

NH2 O

3. 4.
OH O

O OH

5.
OH

CN
 Determine the product of the following
20.10 sequence of reactions.
O SOCl2 CH3MgBr H3O+

NH2 Et2O

2.
1.
O

3.
4.
HO CN
NHCH 3

5.

NH2
20.10 answer

O SOCl2 CH3MgBr H3O+

NH2 Et2O

2.
1.
O

3.
4.
HO CN
NHCH 3

5.

NH2