NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsMedium
Question
Cyanohydrin of which of the following compounds on hydrolysis gives an optically active product?
A
HCHO
B
CH3CHO
C
CH3COCH3
D
All of the above
Step-by-Step Solution
The reaction involves two steps: nucleophilic addition of HCN to form a cyanohydrin, followed by hydrolysis of the cyanide group (-CN) to a carboxylic acid group (-COOH).
HCHO (Formaldehyde):HCHO+HCN→H2C(OH)CNH3O+H2C(OH)COOH
The product is 2-hydroxyethanoic acid (glycolic acid). The central carbon has two identical hydrogen atoms, so it is achiral and optically inactive.
CH3CHO (Acetaldehyde):CH3CHO+HCN→CH3CH(OH)CNH3O+CH3CH(OH)COOH
The product is 2-hydroxypropanoic acid (lactic acid). The central carbon is bonded to four different groups: -H, -OH, -CH3, and -COOH. Thus, it contains an asymmetric carbon (chiral center) and exists as optically active enantiomers.
CH3COCH3 (Acetone):CH3COCH3+HCN→(CH3)2C(OH)CNH3O+(CH3)2C(OH)COOH
The product is 2-hydroxy-2-methylpropanoic acid. The central carbon is bonded to two identical methyl groups, so it is achiral and optically inactive.
Therefore, only acetaldehyde yields an optically active product.
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