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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)
CH3
CH2
H:
b)
+
H
CH2
CH3
CH3
CH2
CH3
CH3
CH3
CN
CH3CH2
C
CH3CH2
:CN-
OH
H+
O:
CH3
3.
OH
O:
O
+
CH3
CH3CH2
CN
CN
CH3
+ OH
13.5 Exercise 2
1.
2.
a)
b)
c)
d)
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
2.
a)
b)
c)
d)
e)
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