Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the
presence of a weak base.
In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases.
Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong
base?
A CH3CH(OH)CO2CH3
B CH3CO2CH2CH(OH)CH3
C CH3CH2CH(OH)CH2CO2CH3
D (CH3)2C(OH)CH2CO2CH3

Question

Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the
presence of a weak base.
In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases.
Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong
base?
A CH3CH(OH)CO2CH3
B CH3CO2CH2CH(OH)CH3
C CH3CH2CH(OH)CH2CO2CH3
D (CH3)2C(OH)CH2CO2CH3

aaronq · Answer

the second is an enolate, |dw:1396840801716:dw|

the carbanion form will attack the C=O carbon of the aldehyde making a secondary alcohol.

Draw the options to see which is the correct one.