When m-chlorobenzaldehyde is treated with 50% KOH solution, the product(s) obtained is (are)
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Answer
(2) [figure]
Solution
m-Chlorobenzaldehyde has no α-hydrogen with concentrated (50%) alkali it undergoes the Cannizzaro reaction (self oxidation–reduction).
2 ClC6H4CHO + KOH ClC6H4COO-K+ + ClC6H4CH2OH
One molecule is oxidised to m-chlorobenzoate and the other is reduced to m-chlorobenzyl alcohol.
The C–Cl bond of the ring is not attacked by the alkali under these conditions, so Cl stays in the meta position.
Answer: (2)