JEE Main Chemistry question
A substituted chloro-ether compound (bearing a -methoxyphenyl ether group and a -nitrophenyl group on either side of a chlorine-bearing, methyl-substituted carbon) undergoes hydrolysis in aqueous acetone. The major and minor hydrolysis products, and , are given below (structures , , ). Which combination represents the actual product mixture?
Solution
Solvolysis in aqueous acetone of this hindered, benzylic-type chloride proceeds through an pathway, via a carbocation that is stabilised by the neighbouring -methoxyphenyl group (through resonance donation from the methoxy-substituted ring). Direct capture of water at the original carbon (with net retention
See the full step-by-step solution
Create a free account to read the complete working, and practise questions like this in a timed test.
Create a free account