Chapter 17, Problem 17.82P

Interpretation Introduction

Interpretation:

From the given data, the structure of the product of the given reaction is to be identified.

Concept introduction:

The $\text{α,β}$$\text{-}$ unsaturated carbonyl compounds have two electrophilic centers. One is the carbonyl carbon yielding the direct addition product; second is the $\text{β}$ carbon yielding the conjugate addition product.

Thus, both can react with the nucleophile, depending on the nature of the nucleophile and the regioselectivity of the reaction.

When the nucleophile adds to the carbonyl carbon, the reaction yields a $\text{1, 2-addtion}$ product, and the final product is alcohol in this case.

When the nucleophile adds to the $\text{β}$ carbon of the carbonyl compound, the reaction yields a $\text{1, 4-addition}$ product, keeping the carbonyl group intact.

The number of signals in the $\text{H}$ NMR indicates the number of distinct hydrogen atoms, and the splitting pattern indicates the number of neighboring hydrogen atoms.

A broad absorption between ${\text{3200 - 3600 cm}}^{\text{-1}}$ in IR spectrum is a characteristic of an $\text{O-H}$ stretching, and a peak near ${\text{1700 cm}}^{\text{-1}}$ is characteristic of the carbonyl group.