JEE MainChemistryAldehydes and Ketones
An , -unsaturated carbonyl compound X ( C ₁₀ H ₁₀ O ) undergoes 1,4-conjugate addition with NaCN followed by acidic hydrolysis to yield compound Y ( C ₁₁ H ₁₂ O ₃ ). Compound Y is formed as a racemic mixture, gives a yellow precipitate with I ₂/ NaOH , and produces effervescence with aqueous NaHCO ₃ . Identify the two starting materials that undergo cross-aldol condensation to synthesize compound X.
Options
- ABenzaldehyde and Acetone
- BAcetophenone and Acetaldehyde
- CBenzaldehyde and Propanal
- DPhenylacetaldehyde and Acetaldehyde
Correct answer
A. Benzaldehyde and Acetone
Step-by-step solution
Compound Y gives effervescence with aqueous NaHCO ₃ , indicating the presence of a carboxylic acid ( - COOH ) group, which is formed by the hydrolysis of the - CN group added via 1,4-conjugate addition. Compound Y gives a yellow precipitate with I ₂/ NaOH (positive iodoform test), indicating the presence of a methyl ketone ( - CO - CH ₃ ) group. Since Y is formed by the 1,4-addition of cyanide to X followed by hydrolysis, X must be an , -unsaturated methyl ketone with the molecular formula C ₁₀ H ₁₀ O . Let us eval