Question

Draw a structure for the product of nucleophilic substitution obtained on solvolysis of tert-butyl bromide in methanol, and arrange the correct mechanism for its formation. Draw all lone pairs of electrons

Answer 1

Reaction goes through
`S_(N)1` mechanism.

Step-by-step explanation:

Solvolysis of tert-butyl bromide in methanol gives methyl tert-butyl ether as major product obtained from nucleophilic substitution of bromine atom by methanol.

Reaction mechanism goes through
`S_(N)1` mechanism.

In the first step, a tert-butyl carbocation is produced. This is the rate limiting step.

In the second step, methanol attacks the carbocation and gets bind to it through a covalent bond.

In the third step, deperotonation occurs to give methyl tert-butyl ether.

Reaction mechanism has been shown below.