Chemistry 108

Chapter 10 Reactions Worksheet and Key

Chapter 10 Reactions Worksheet and Key

1. Acidity of Carboxylic Acids:
The hydroxyl H atom is weakly acidic (ionizes ~ 0.5 %).
O
O
||
||
R C OH
+ H2O (l)
R C O- (aq) + H3O+ (aq)
RCOO is the carboxylate ion, and is much more soluble than the parent acid because it has
a charge (it is an ion).
Nomenclature of carboxylate ions is done by changing the "ic acid" suffix of the parent
acid to "ate ion".
Note that the reaction is reversible, the carboxylate ion can be converted to the carboxylic acid
form under acidic conditions (neutralization of a base with an acid):
O
O
||
||
+
R C O (aq) + H3O (aq)
R C OH
+ H2O (l)

or

O
||
R C O- (aq) +

HCl (aq)

O
||
R C OH

Cl- (aq)

Likewise, The acid form can be converted to the base form (carboxylate ion) under basic
conditions (neutralization of an acid with a base):
O
||
R C OH

O
||
R C O- (aq)

+ OH-(aq)

H2O (l)

2. Basicity of Amines:
The nitrogen lone pair can accept hydrogen from water or a strong acid
R
|
R N:
|
H
R
|
R N:
|
H

+ H2O

R
|+
R N H +
|
H

OH-

+ HCl

R
|+
R N H +
|
H

Cl-

Chemistry 108

Chapter 10 Reactions Worksheet and Key

3. Reactions of Carboxylic Acids

a) Ester Formation

Esterification is carried out by warming a mixture of a carboxylic acid and an alcohol in the
presence of a strong acid catalyst.

Note that the reaction is reversible!

Esters undergo hydrolysis to give back the carboxylic acid.
we saw this in chapter 6!
Ester hydrolysis reactions can be catalyzed by either an acid or a base. Here is the net result:

b) Decarboxylation

Break the COOH off, and add an H where it was

O
||
RCOH
R H + CO2

Chemistry 108

Chapter 10 Reactions Worksheet and Key

c) Formation of Amides
Amides are formed by reaction of an amine with a carboxylic acid. This is an endothermic reaction
(requires energy). In biological systems, where it is not possible to use heat, a specific enzyme is needed
a) Reaction of carboxylic acids and ammonia (NH3)
O
O
||
||
R C OH + H N H
R C NH2
|
H
b) Reaction of carboxylic acids and primary (1o) amines (NH2R)
O
||
R C OH + H N R
|
H

O
||
R C NR
|
H

+ H2O

+ H2O

c) Reaction of carboxylic acids and secondary (2o) amines (NHR2)

O
||
R C OH + H N R
|
R

O
||
R C N R
|
R

+ H2O

d) Reaction of carboxylic acids and tertiary (3o) amines (HR3)

NO REACTION occurs with tertiary (3o) amines

Examples:

Chemistry 108

Chapter 10 Reactions Worksheet and Key

1) Write the chemical equation for the reaction of propanoic acid with 1-butanol (an alcohol).
The formula of 1-butanol is CH3-CH2-CH2-CH2-OH.

2) Write the chemical equation for the reaction of ethanoic acid with N-methylethanamine.

3) Write the chemical equation for the reaction that occurs when the pentanoate ion is neutralized by
hydrochloric acid (HCl).

4) Write the chemical equation for the decarboxylation of 2-methyl-propanoic acid.

5) Write the chemical equation for the reaction of propanoic acid with water.

Chemistry 108

Chapter 10 Reactions Worksheet and Key

6) Write the chemical equation for the reaction of N,N-diethyl-1-propanamine with water.
(Hint: the amine is a base):

7) Complete the following reactions:

a)
O
||
CH3CH2CH2CH2 C OH (aq) +

H2O (l)

b)

CH3 N H (aq)
|
CH2CH3

+ H2O (l)

c)
O
||
CH3CH2 C OH (aq) + NaOH (aq)

d)
O
||
CH3 C O H + CH3CH2 CHCH2OH
|
CH2CH3
5

Chemistry 108

Chapter 10 Reactions Worksheet and Key

e) decarboxylation
O
||
CH3CH2 C O H

CO2

f)
O
||
CH3CH2 C O H

+ NH3

g)
O
||
CH3CH2 CHCH2 C O H
|
CH3

+ CH3OH

h)
O
||
CH3 CH2 C O H +

HNCH2CH3
|
CH2CH3

i)
O
||
CH3 CH2 C O-

+ HCl

Chemistry 108

Chapter 10 Reactions Worksheet and Key

8) Fill in the missing reactant(s):

a)

CH3 CH2CH2CH3

+ CO2

(decarboxylation reaction)

b)
O
||
CH3CH2CH2 C NCH3 +
|
H

H-O-H

c)
+ CH3OH

O
||
CH3CH2 CHCH2 C O CH3 + H2O
|
CH3

d)

H2O (l)

O
||
CH3CH2CH2CH2 C O- (aq) + H3O+ (aq)

e)

+ H2O (l)

H
|+
CH3CH2CH2 N H (aq) + OH- (aq)
|
CH2CH3

Chemistry 108

Chapter 10 Reactions Worksheet and Key

f)

O
||
CH3CH2 C OH (aq) +

O
||
CH3CH2 C O- Na+ (aq)

H2O (l)

g)
O
||
CH3 CH2 C O H +

O
||
CH3CH2 C O CH2CHCH2CH3 + H2O
|
CH2CH3

h)

HNCH2CH3
|
CH2CH3

O
||
CH3CH2 C NCH2CH3
|
CH2CH3

+ H2O

i)

+ HCl

O
||
CH3 CH2C OH + Cl-

Chemistry 108

Chapter 10 Reactions Worksheet and Key

Key
1) Write the chemical equation for the reaction of propanoic acid with 1-butanol (an alcohol).
The formula of 1-butanol is CH3-CH2-CH2-CH2-OH.
O
||
CH3CH2 C O H + CH3CH2 CH2 CH2OH

O
||
CH3CH2 C O CH2CH2 CH2 CH3 + H2O

2) Write the chemical equation for the reaction of ethanoic acid with N-methylethanamine.
O
||
CH3 C O H + H N CH2CH3
|
CH3

O
||
CH3 C N CH2CH3 + H2O
|
CH3

3) Write the chemical equation for the reaction that occurs when the pentanoate ion is neutralized by
hydrochloric acid (HCl).
O
||
CH3 CH2 CH2CH2C O -

+ HCl

O
||
CH3 CH2 CH2CH2C OH + Cl-

4) Write the chemical equation for the decarboxylation of 2-methyl-propanoic acid.

O
||
CH3CH C O H
|
CH3

CH3CH2 CH3 + CO2

5) Write the chemical equation for the reaction of propanoic acid with water.
O
||
CH3CH2 C OH (aq) +

H2O (l)

O
||
CH3CH2 C O- (aq)

H3O+ (aq)

Chemistry 108

Chapter 10 Reactions Worksheet and Key

6) Write the chemical equation for the reaction of N,N-diethyl-1-propanamine with water.
(Hint: the amine is a base):
H
|+
CH3CH2 N CH2CH3 (aq) + OH- (aq)
|
CH2CH2CH3

CH3CH2 N CH2CH3 (aq) + H2O (l)

|
CH2CH2CH3
7) Complete the following reactions:
a)
O
||
CH3CH2CH2CH2 C OH (aq) +

H2O (l)

O
||
CH3CH2CH2CH2 C O- (aq) + H3O+ (aq)

b)

CH3 N H (aq) + H2O (l)

|
CH2CH3

H
|+
CH3 N H (aq) + OH- (aq)
|
CH2CH3

c)
O
||
CH3CH2 C OH (aq) +

NaOH (aq)

O
||
CH3CH2 C O- Na+ (aq)

H2O (l)

d)
O
||
CH3 C O H + CH3CH2 CHCH2OH
|
CH2CH3

O
||
CH3 C O CH2CH CH2CH3 + H2O
|
CH2CH3

10

Chemistry 108

Chapter 10 Reactions Worksheet and Key

e)
O
||
CH3CH2 C O H

CH3CH3

+ CO2

f)
O
||
CH3CH2 C O H + NH3

O
||
CH3CH2 C NH2

H-O-H

g)
O
||
CH3CH2 CHCH2 C OH + CH3OH
|
CH3

O
||
CH3CH2 CHCH2 C O CH3 + H2O
|
CH3

h)
O
||
CH3 CH2 C OH

HNCH2CH3
|
CH2CH3

O
||
CH3CH2 C NCH2CH3
|
CH2CH3

+ H2O

i)
O
||
CH3 CH2 C O-

+ HCl

O
||
CH3 CH2C OH + Cl-

8. Fill in the missing reactant(s):

a)
O
||
CH3 CH2CH2 CH2 C O H

CH3 CH2CH2CH3

+ CO2

11

Chemistry 108

Chapter 10 Reactions Worksheet and Key

b)
O
||
CH3CH2 CH2 C OH + CH3NH2

O
||
CH3CH2 CH2 C NCH3 +
|
H

H-O-H

c)
O
||
CH3CH2 CHCH2 C OH + CH3OH
|
CH3

O
||
CH3CH2 CHCH2 C O CH3 + H2O
|
CH3

d)
O
||
CH3CH2CH2CH2 C OH (aq) + H2O (l)

O
||
CH3CH2CH2CH2 C O- (aq) + H3O+ (aq)

e)

CH3CH2CH2 N H (aq) + H2O (l)

|
CH2CH3

H
|+
CH3CH2CH2 N H (aq) + OH- (aq)
|
CH2CH3

f)

O
||
CH3CH2 C OH (aq) +

NaOH (aq)

O
||
CH3CH2 C O- Na+ (aq)

H2O (l)

12

Chemistry 108

Chapter 10 Reactions Worksheet and Key

g)
O
||
CH3 CH2 C OH + CH3CH2 CHCH2OH
|
CH2CH3

O
||
CH3CH2 C O CH2CHCH2CH3 + H2O
|
CH2CH3

h)
O
||
CH3 CH2 C OH

HNCH2CH3
|
CH2CH3

O
||
CH3CH2 C NCH2CH3
|
CH2CH3

+ H2O

i)
O
||
CH3 CH2 C O-

+ HCl

O
||
CH3 CH2C OH + Cl-

13