Compare Reactivity of Alcohol and Phenol

In phenol -OH group is directly bonded to benzene.

The lone pair of oxygen can interact with the delocalised pi system of benzene and resonance stability is extended to C-O bond.

230220 phenol resonance stabilised

This makes the C-O bond very stable and phenol does not take part in substitution and elimination reactions like alcohol.

Therefore phenol will have significantly fewer reactions compared to alcohol, since both alcohol's C-O and O-H bonds can be broken.

Let's compare the reactivity and types of reaction for alcohol and phenol.

230220 compare reactivity alcohol and phenol

For alcohols:

Types of reaction when C-O bond is broken include nucleophilic substitution and elimination.

Types of reaction when O-H bond is broken include oxidation (C-H bond is also broken), neutralisation and condensation.

For phenols:

Since C-O bond is resonance stabilised and not broken, there is no nucleophilic substitution and elimination.

O-H bond can still be broken hence phenols can take part in neutralisation and condensation reactions.

Check out this video to learn all the reactions of alcohols and phenols.

Topic: Alcohol, Organic Chemistry, A Level Chemistry, Singapore

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