Which of the following on heating with aqueous KOH , produces acetaldehyde ?
(A)CH3COCl
(B)CH3CH2Cl
(C)CH2ClCH2Cl
(D)CH3CHCl2✓ Correct
Answer: (D)
Solution
A gem-dihalide, with both halogens on the same carbon, hydrolyses with aqueous potassium hydroxide to a carbonyl compound. Here CH3CHCl2 first gives the unstable gem-diol CH3CH(OH)2, which at once loses water to yield acetaldehyde, CH3CHO. The other compounds do not give acetaldehyde under these conditions.
JEE Main · 2009 · 12 Apr 2009 · Offline · Single correct option