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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

  1. AOne optically active and one meso product
  2. BA racemic mixture
  3. CTwo optically inactive products
  4. 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)

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