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 61P
Interpretation Introduction

Interpretation:The reason behind excess usage of methyl magnesium iodide andmethyl lithium and number of equivalents of methyl magnesium iodide and methyl lithiumneeded in each case along with the products formed at functionalized sites should be given.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 61P , additional homework tip  1

Concept introduction: 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 61P , additional homework tip  2

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 61P , additional homework tip  3

Methyl bromide reacts with magnesium ether to give Grignard reagent. This Grignard methyl magnesium 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 61P , additional homework tip  4

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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