Question

Reaction of hexamethylbenzene with methyl chloride and aluminum chloride gave a salt a, which, on being treated with aqueous sodium bicarbonate solution, yielded compound

b. suggest a mechanism for the conversion of hexamethylbenzene to b by correctly inferring the structure of a

Answer 1

Answer: -

The first step involves reaction of methyl chloride with AlCl₃.

Then the compound A generates by attack of pi bond on CH₃.

Then there is a rearrangement of the carbocation from 2° to 3°.

Finally a H⁺ is lost to give B