Q28E 2-Bromo-6, 6-dimethylcyclohexano... [FREE SOLUTION]

Chapter 20: Q28E (page 678)

2-Bromo-6, 6-dimethylcyclohexanone gives 2, 2-dimethylcyclopentane-carboxylic acid on treatment with aqueous NaOH followed by acidification, a process called the Favorskii reaction. Propose a mechanism.

Short Answer

Expert verified

dimethylcyclohexanone gives 2, 2-dimethylcyclopentane-carboxylic acid on treatment with A mechanism for the Favorski rearrangement, in which 2-bromo-6, 6-aqueous NaOH is shown below

Step by step solution

Definition of mechanism

The sequence of elementary steps by which a chemical reaction occurs is defined as mechanism

Mechanism for the Favorski rearrangement

The nucleophilic attack of the hydroxide ion on the carbonyl carbon in 2 bromo-6, 6-dimethylcyclohexanone yields an oxyanion. The flow of electrons from the negatively charged oxygen followed by breaking of the $C_{1} - C_{6}$ bond and the formation of $C_{6} - C_{2}$ bond eliminates a bromide ion to yield cyclopentane carboxylic acid.

A mechanism for the Favorski rearrangement, in which 2-bromo-6, 6-dimethylcyclohexanone gives 2, 2-dimethylcyclopentane-carboxylic acid and bromide ion on treatment with aqueous NaOH