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
Question
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Chapter 8, Problem 44P

(a)

Interpretation Introduction

Interpretation:The mechanism for the major product formation in the indicated reaction should be written.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  1

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  2

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , 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 44P , 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.

(b)

Interpretation Introduction

Interpretation:The mechanism for the major product formation in the indicated reaction should be written.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  5

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  6

Grignard reagents are alkyl magnesium halides obtained from treatment of haloalkane with magnesium in presence of dried ether conditions. This reagent is 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 44P , additional homework tip  7

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 44P , additional homework tip  8

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.

(c)

Interpretation Introduction

Interpretation:The mechanism for the major product formation in the indicated reaction should be written.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  9

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  10

Grignard reagents are alkyl magnesium halides obtained from treatment of haloalkane with magnesium in presence of dried ether conditions. This reagent is 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 44P , additional homework tip  11

(d)

Interpretation Introduction

Interpretation:The mechanism for the major product formation in the indicated reaction should be written.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  12

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  13

Grignard reagents are alkyl magnesium halides obtained from treatment of haloalkane with magnesium in presence of dried ether conditions. This reagent is 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 44P , additional homework tip  14

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 44P , additional homework tip  15

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.

(e)

Interpretation Introduction

Interpretation: The mechanism for the major product formation in the indicated reaction should be written.

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  16

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

  Organic Chemistry: Structure and Function, Chapter 8, Problem 44P , additional homework tip  17

Grignard reagents are alkyl magnesium halides obtained from treatment of haloalkane with magnesium in presence of dried ether conditions. This reagent is 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 44P , additional homework tip  18

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 44P , additional homework tip  19

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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