4.

5 ANSWERS TO EXERCISES

4.5 Exercise 1

1.
a) propanoic acid b) propan-1-ol c) no reaction
H H
O H H H

H C C C H C C C OH
OH
H H H H H

d) propan-2-ol e) 2-hydroxymethylpropanenitrile
OH
H OH H
CH3 C C N
H C C C H

H H H CH3

f) butanoic acid g) methylpropanoic acid h) no reaction

H H
O
H C C C
H H H
O OH
H C
H C C C C
H H
OH
H H H H

i) 2-hydroxy,2-methylbutanenitrile
OH

CH3 CH2 C C N

CH3

2. a) CH3CH2COCH3 + 2[H]  CH3CH2CH(OH)CH3

 - - H O H
O : H
O
+ O -
C H C H
C H 3 C H 2
C H + O H
3 2 C C H 3 C H 2 C H
C H 3
C H 3
C H
- 3

H :
b) CH3CH2COCH3 + HCN  CH3CH2CH(CH3)CN
 - O H
+ O
 -
 -
+ O : H +
 C H 3 C H 2
C C H 3 C H 2
C C N
H C N C
C H C H C N
C H 3 2
3 C H 3
C H 3
:C N -

3. a) propanal and HCN b) butanone and HCN c) methylpropanal and HCN

4.5 Exercise 2

1. a) CH3CH2COOH + NaOH  CH3CH2COO-Na+ + H2O

b) 2CH3CH2CH2COOH + Na2CO3  2CH3CH2CH2COO-Na+ + CO2 + H2O
c) HCOO-Na+ + HCl  HCOOH + NaCl
d) 2CH3COO-Na+ + H2SO4  2CH3COOH + Na2SO4
e) 2CH3CH(CH3)COOH + Na2CO3  2CH3CH(CH3)COO-Na+ + CO2 + H2O

2. a) CH3CH2COOH + CH3OH == CH3CH2COOCH3 + H2O

organic product = methyl propanoate
b) CH3COOH + CH3CH(OH)CH3 == CH3COOCH(CH3)CH3 + H2O
organic product = methylethyl ethanoate
c) HCOOH + CH3CH2CH2OH == HCOOCH2CH2CH3 + H2O
organic product = propyl methanoate
d) CH3CH2CH2COOH + CH3CH2CH2CH2OH == CH3CH2CH2COOCH2CH2CH2CH3 + H2O
organic product = butyl butanoate

3. a)
O
O

+ H2O H C + CH3 CH2 OH

H C
OH
O CH2 CH3

b)
O
O
CH3 CH2 C + CH3 OH
CH3 CH2 C + NaOH O Na- +
O CH3

c)
OH
O H
O
CH3 C
O CH CH3 + H2O
H C C + CH3 C CH3
OH

CH3 H H

d)
O
O
H C
O
+ NaOH H C + CH3 CH2 CH2 OH
CH2 CH2 CH3
O Na- +

4.
a)
 H
O
H

H C O C C15H31
O H C OH
O

H C + 3H2O H C OH
C O C15H31
+ 3 HO C C15H31
O
H C OH
H C O C C15H31
H

b)

H
O
H

H C O C C15H31
OH
O H C
O

+ 3NaOH -
H C O C C15H31 H C OH
+ 3 Na+O C C15H31
O
H C OH

H C O C C15H31
H

H
Reaction (a) takes place in the stomach
The fatty acids are used in cell membranes
The glycerol is used as an energy source
Reaction (b) is carried out industrially
The glycerol is used in pharmaceutical and cosmetic preparations
The carboxylate salts are used as soaps

4.5 Exercise 3

1. a) CH3CH2COCl + 2NH3  CH3CH2CONH2 + NH4Cl

organic product: propanamide
b) (CH3CH2CH2CO)2O + CH3CH(OH)CH3  CH3CH2CH2COOCH(CH3)CH3 + CH3CH2CH2COOH
organic products: methylethyl butanoate and butanoic acid
c) HCOCl + 2CH3CH2NH2  HCONHCH2CH3 + CH3CH2NH3+Cl-
organic product: N-ethyl methanamide
d) (CH3CO)2O + CH3CH(NH2)CH3  CH3CONHCH(CH3)CH3 + CH3COOH
organic products: N-methylethylethanamide and ethanoic acid
e) CH3CH(CH3)COCl + H2O  CH3CH(CH3)COOH + HCl
organic products: methylpropanoic acid

2. a)
 H
O

H C C + CH3 CH2 OH
Cl
H

b)
H H
O
H C C C + CH3 NH2
Cl
H H

c)
OH
O

CH3 CH2 C + CH3 C CH3

Cl
H

d)
O
H C + CH3 CH2 NH2
Cl
e)
O OH
O
C
CH3 C
O H + O
CH3 C
O

3. a)

- O-
+  - O
 O O C. . l
C H C C + H C l
3
C H 3 C C l C H 3
C l C H 3 C
+ N C H 3

.. + N H
H N
N C H 3 H
C H 3
C H H H
3
H H

b) nucleophilic addition-elimination
c) acid anhydride is cheaper than acyl chloride
the acid anhydride reaction is less violent
the acid anhydride reaction does not produce toxic fumes of HCl