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Hydrolysis of Geminal Dihalides

Benzylic and allylic positions are especially reactive and can be doubly halogenated with a free-radical halogenating reagent.

Hydrolysis of geminal dihaloalkanes

Double bromination of a benzylic position with two equivalents of NBS

Click here to recall the halogenation of alkanes.

Click here to recall what an allylic position is.

Click here to recall what a benzylic position is.

The resulting dihaloderivative is easily transformed into a ketone by treatment with sodium hydroxide.

Hydrolysis of the geminal dibromide with water and hydroxide to a ketone

Does the reaction make sense to you?

Click here to review SN and elimination reactions.