will phenol undergoes neuclophilic substituion reaction?why or why not.

Asked by Ridika Acharya | 14th Jul, 2013, 01:24: PM

Expert Answer:

Phenol does not undergo nucleophilic substitution reaction  :

1. Due to Resonance(+R) effect, the oxygen gets attached to the C on the benzene ring and acquires a partial double bond character, making it tough to break. difficult to break.

2.The oxygen being attached to an sp3 hybridised carbon, the bond length becomes shorter ,also making it difficult to break.

3.The approach of electron rich nucleophile towards the electron rich benzene ring is less probable  owing to repulsion.

Answered by  | 14th Jul, 2013, 11:20: PM

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