ANSWERS TO ASSIGNMENT 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 OH
O: H
O
+ O -
CH3 CH2
CH3 CH2 C H + OH
C CH3 CH2 C H
CH3
CH3
CH3
-
H:
b) CH3CH2COCH3 + HCN  CH3CH2CH(CH3)CN
- OH
+ O
 -
-
+ O: H+
 CH3CH2 C CH3CH2 C CN
H CN
CH3CH2 C CN
CH3
CH3
CH3
:CN-
3. a) propanal and HCN b) butanone and HCN c) methylpropanal and HCN