Propose a Williamson synthesis of

Solution:

Here we have to propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethylcyclohexanol and butan-1-ol.

Step 1

Williamson synthesis involves SN2 mechanism. In this reaction the nucleophile attacks a methyl carbon(1o  of the butyl group) instead of forming bond from oxygen to the  2o carbon on the cyclohexane ring.

 1-butanol undergoes chemical reaction in presence of TsCl (p-toluenesulfonyl chloride) and pyridine, in  which the -OH group has been transferred into a good leaving group.