What is the primary organic product formed when benzaldehyde is treated with hydrogen cyanide () in the presence of catalytic potassium cyanide?
Answer and explanation
Correct answer: D. Mandelonitrile (2-hydroxy-2-phenylacetonitrile)
- Step 1: In the presence of a basic catalyst, cyanide ion () acts as a strong nucleophile and attacks the carbonyl carbon of benzaldehyde.
- Step 2: The resulting alkoxide intermediate abstracts a proton from to form a cyanohydrin.
- Step 3: The product formed from benzaldehyde is mandelonitrile: .
Answer
Mandelonitrile (2-hydroxy-2-phenylacetonitrile).
Why not the others: Benzoic acid requires oxidation; Benzylamine requires reduction of benzonitrile; Benzonitrile lacks the hydroxyl group.
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