Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8, Problem 50P
Interpretation Introduction

Interpretation: The structures of A and B that should to be determined.

Concept introduction:The alcohols are best synthesized from retrosynthetic analysis with the aid of Grignard reagents.

The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 50P , additional homework tip  1

Grignard reagents are alkyl magnesium halides obtained from treatment of haloalkane with magnesium in presence of dried ether conditions. Theses reagent are useful precursor for quick synthesis of variety of organic compounds For example, the reaction of Grignard reagent with aldehyde or ketone generates alcoholsas illustrated below.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 50P , additional homework tip  2

Methyl bromide reacts with magnesium ether to give Grignard reagent. This Grignard methylmagnsium bromide on treatment with formaldehyde gives corresponding alcohol. The mechanistic pathway for the latter reaction is as follows:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 50P , additional homework tip  3

The polar carbonyl bond breaks and the polar Grignard reagent attack at electron deficient carbon. Finally with the hydrolysis and work up the alcohol is formed.

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