Chapter 17, Problem 17.64P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

In an $\text{α,β-}$ unsaturated carbonyl, nucleophiles in general can attack at two positions, either at the carbonyl carbon or at the $\text{β}$ carbon. Attack of the nucleophile at the carbonyl carbon is called 1, 2-addition or direct addition. Attack at the $\text{β}$ C atom, on the other hand, is called 1, 4-addition or conjugate addition. The 1, 4-addition product is an enol, which rapidly tautomerizes to generate the more stable keto form as the major product, and the keto form can be further reduced to an alcohol. The 1, 2-addition or direct addition product is an allylic alcohol.