Chapter 15, Problem 27P

Interpretation Introduction

Interpretation:

Using $1-\text{bromobutane}$ and the necessary organic or inorganic reagents, the synthesis of the given alcohols is to be suggested.

Concept introduction:

Grignard reagents and their lithium analogs are prepared by the reaction of the metal with an alkyl (primary, secondary, tertiary), aryl, or vinyl halide, usually in diethyl ether as the solvent.

Retrosynthesis of alcohols provides useful information about the carbonyl compounds that could be used to produce alcohols upon reaction with Grignard reagents.

The type of alcohol – primary, secondary or tertiary – suggests the possible carbonyl compounds used.

Primary alcohols are produced by the reaction of Grignard reagent with formaldehyde.

Secondary alcohols are produced by the reaction of Grignard reagent with aldehydes.

Tertiary alcohols are produced by the reaction of Grignard reagent with ketones.