Chapter 22, Problem 22.16P

Interpretation Introduction

Interpretation:

It is to be shown how to carry out the given synthesis without using the Clemmensen reduction.

Concept introduction:

The carbonyl group of the ketone is best reduced to corresponding secondary alcohol by the treatment of sodium borohydride (${\text{NaBH}}_{\text{4}}$). Alcohol, on treatment with either concentrated sulfuric acid (${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$) or phosphoric acid (${\text{H}}_{\text{3}}{\text{PO}}_{\text{4}}$), undergoes dehydration to produce an alkene. An alkene, on catalytic hydrogenation with ${\text{H}}_{\text{2}}\text{, Pt}$, leads to form the corresponding alkane.