JEE Main 2024 · 30 January · evening · Single correct · +4 / −1
m-chlorobenzaldehyde on treatment with 50% KOH solution yields :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (a)
Solution
Chemistry ma’am · 4 steps
No α-hydrogen plus strong alkali means Cannizzaro: one aldehyde is oxidised, the other reduced.
- Spot the reaction. The -CHO group sits directly on the ring, so there is no α-hydrogen and aldol condensation is impossible. In concentrated (50%) KOH, such an aldehyde undergoes the Cannizzaro reaction.
- Hydride transfer. OH⁻ adds to the carbonyl carbon of one molecule. That adduct passes a hydride ion (H⁻) to the carbonyl carbon of a second molecule. The first becomes a carboxylate (oxidised), and the second becomes an alkoxide that picks up a proton to give an alcohol (reduced).
2 ClC₆H₄CHO + KOH → ClC₆H₄COO⁻ K⁺ + ClC₆H₄CH₂OH
- Chlorine stays put. The aryl C-Cl bond has partial double-bond character from resonance with the ring. Hydroxide cannot replace it under these mild conditions, so the Cl remains at the meta position in both products.
- So. The products are the m-chlorobenzoate ion and m-chlorobenzyl alcohol, which is option (a).
The idea to keep. Aldehyde with no α-H in concentrated NaOH or KOH: think Cannizzaro, giving a carboxylate salt plus an alcohol. Ring substituents like an aryl Cl just ride along unchanged.
Answer from the NTA final answer key. Solution by PrepWiser.