The compound A, C8H8O2 reacts with acetophenone to form a single product via cross-Aldol condensation. The compound A on reaction with conc. NaOH forms a substituted benzyl alcohol as one of the two products. The compound A is :
- 2-hydroxy acetophenone
- 4-hydroxy benzaldehyde
- 4-methyl benzoic acid
- 4-methoxy benzaldehyde
Answer
(4) 4-methoxy benzaldehyde
Solution
A with conc. NaOH gives a substituted benzyl alcohol and a carboxylate (Cannizzaro reaction) A is an aromatic aldehyde with no α-hydrogen.
A has no α-hydrogen, only acetophenone forms the enolate in the cross-aldol (Claisen–Schmidt) reaction a single product.
4-Methoxybenzaldehyde, CH3O-C6H4-CHO = C8H8O2, fits both.
Other options: 2-hydroxyacetophenone is a ketone (no Cannizzaro reaction); 4-hydroxybenzaldehyde is C7H6O2; 4-methylbenzoic acid is an acid, not an aldehyde.
Cannizzaro: 2 CH3OC6H4CHO conc. NaOH CH3OC6H4CH2OH + CH3OC6H4COONa
Cross-aldol: CH3OC6H4CHO + C6H5COCH3 OH- CH3OC6H4CH=CHCOC6H5 + H2O
Answer: (4)