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JEE Main · 2004 · 24 Apr 2004 · Offline · Aldehydes Ketones and Carboxylic Acids

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Which of the following undergoes reaction with sodium hydroxide solution to give the corresponding alcohol and acid?
  1. (A)Phenol
  2. (B)Benzoic acid
  3. (C)Butanal
  4. (D)Benzaldehyde✓ Correct

Answer: (D)

Solution

An aldehyde with no alpha-hydrogen cannot undergo aldol condensation, so in concentrated alkali it disproportionates instead through the Cannizzaro reaction. Benzaldehyde fits exactly: with sodium hydroxide one molecule is oxidised to benzoate and another reduced to benzyl alcohol, . Butanal has alpha-hydrogens and would instead give an aldol product, while phenol and benzoic acid do not react this way, leaving benzaldehyde as the one giving the alcohol and the acid.

JEE Main · 2004 · 24 Apr 2004 · Offline · Single correct option

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