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13.

5 ANSWERS TO EXERCISES
13.5 Exercise 1
1.
a) propanoic acid
H

b) propan-1-ol

C
OH

d) propan-2-ol

c) no reaction
OH

e) 2-hydroxymethylpropanenitrile
OH

OH H

CH3

f) butanoic acid

g) methylpropanoic acid
H

H
H

CH3

H
H

O
C

H
O
C

C
OH

h) no reaction

OH
H

i) 2-hydroxy,2-methylbutanenitrile
OH
CH3

CH2

CH3

2.

a)

CH3CH2COCH3 + 2[H] CH3CH2CH(OH)CH3


-

CH3

CH2

H:

b)

+
H

CH2

CH3

CH3

CH2

CH3

CH3

CH3

CH3CH2COCH3 + HCN CH3CH2CH(CH3)CN


-

CN

CH3CH2

C
CH3CH2

:CN-

a) propanal and HCN

OH

H+

O:

CH3

3.

OH

O:

O
+

b) butanone and HCN

CH3

CH3CH2

CN

CN

CH3

c) methylpropanal and HCN

+ OH

13.5 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
CH3COOH + CH3CH(OH)CH3 == CH3COOCH(CH3)CH3 + H2O
organic product = methylethyl ethanoate
HCOOH + CH3CH2CH2OH == HCOOCH2CH2CH3 + H2O
organic product = propyl methanoate

b)
c)
d)

CH3CH2CH2COOH + CH3CH2CH2CH2OH == CH3CH2CH2COOCH2CH2CH2CH3 + H2O

organic product = butyl butanoate


3.

a)
O

C
O

CH2

H2O

CH3

CH2

+
O- Na+

CH3

OH

OH

CH3

b)
O

CH3

CH2

C
O

CH2

CH3

NaOH

CH3

OH

c)
OH
O

CH3

C
O

CH

CH3

H2O

CH3

CH3

OH
H

CH3

d)
O

C
O

4.
a)

CH2

CH2

CH3

NaOH

- +

O Na

CH3

CH2

CH2

OH

H
O

O
C

C15H31

C15H31

3H2O

OH

OH

OH

C15H31

HO

C15H31

b)
H
O

H
H

C
C

C
O

C15H31

C15H31

+ 3NaOH

C15H31

OH

OH

OH

Na +O

C15H31

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
13.5 Exercise 3
1.

2.

a)

CH3CH2COCl + NH3 CH3CH2CONH2 + HCl


organic product: propanamide

b)

(CH3CH2CH2CO)2O + CH3CH(OH)CH3 CH3CH2CH2COOCH(CH3)CH3 + CH3CH2CH2COOH

c)

organic products: methylethyl butanoate and butanoic acid


HCOCl + CHCHNH HCONHCHCH + HCl
organic product: N-ethyl methanamide

d)

(CH3CO)2O + CH3CH(NH2)CH3 CH3CONHCH(CH3)CH3 + CH3COOH

e)

organic products: N-methylethylethanamide and ethanoic acid


CH3CH(CH3)COCl + H2O CH3CH(CH)COOH + HCl
organic products: methylpropanoic acid

a)

H
H

CH3

OH

CH2

Cl
H

b)
H

O
H

NH2

CH3

Cl

c)
OH
O

CH2

CH3

CH3

Cl

CH3

d)
O
H

CH3

NH2

CH2

Cl

e)
O

OH
O

C
O

CH 3

C
O

CH 3

C
O

3.

a)

CH3

C
Cl

..
N
CH3

b)
c)

H
H

O-

CH 3

Cl

CH3

+
N

CH 3

CH3

Cl
..

CH3

+
N

+ HCl

C
N

H
H
H

nucleophilic addition-elimination
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

CH 3