JEE MainChemistryAldehydes and Ketones
Consider the following reaction sequence: (2R)-2-hydroxypropanal (i) HCN (ii) H ₃ O ^+ Products The products formed in the above reaction are:
Options
- AOne optically active and one meso product
- BA racemic mixture
- CTwo optically inactive products
- DTwo optically active products
Correct answer
D. Two optically active products
Step-by-step solution
The starting material, (2R)-2-hydroxypropanal, contains one chiral center. Step (i): Nucleophilic addition of HCN to the planar aldehyde group creates a new chiral center at C1. Since the attack can occur from either face of the carbonyl group, two diastereomeric cyanohydrins are formed. Step (ii): Acidic hydrolysis of the cyano group (-CN) converts it into a carboxylic acid group (-COOH). The final products are the two diastereomers of 2,3-dihydroxybutanoic acid. The structure of the product is CH ₃ -CH(OH)-CH(OH)