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NEET CHEMISTRYMedium

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).

  1. HCHO (Formaldehyde): HCHO+HCNH2C(OH)CNH3O+H2C(OH)COOHHCHO + HCN \rightarrow H_2C(OH)CN \xrightarrow{H_3O^+} H_2C(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.

  2. CH3CHO (Acetaldehyde): CH3CHO+HCNCH3CH(OH)CNH3O+CH3CH(OH)COOHCH_3CHO + HCN \rightarrow CH_3CH(OH)CN \xrightarrow{H_3O^+} CH_3CH(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.

  3. CH3COCH3 (Acetone): CH3COCH3+HCN(CH3)2C(OH)CNH3O+(CH3)2C(OH)COOHCH_3COCH_3 + HCN \rightarrow (CH_3)_2C(OH)CN \xrightarrow{H_3O^+} (CH_3)_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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