Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 11.13, Problem 25P

(a)

Interpretation Introduction

Interpretation: The alkyl halide that is used to form the given carboxylic acid has to be identified.

Concept introduction: The reaction of alkyl halides with sodium cyanide gives alkyl cyanides or nitriles. After the reaction there is increase incarbon atoms of the alkyl chain of alkyl halide. The nitriles obtained undergo hydrolysis reaction in presence of acid and gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  1

The hydrolysis reaction of alkyl nitrile in presence of acid is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The alkyl halide that is used to form the given carboxylic acid has to be identified.

Concept introduction: The reaction of alkyl halides with sodium cyanide gives alkyl cyanides or nitriles. After the reaction there is increase incarbon atoms of the alkyl chain of alkyl halide. The nitriles obtained undergo hydrolysis reaction in presence of acid and gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  3

The hydrolysis reaction of alkyl nitrile in presence of acid is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: The alkyl halide that is used to form the given carboxylic acid has to be identified.

Concept introduction: The reaction of alkyl halides with sodium cyanide gives alkyl cyanides or nitriles. After the reaction there is increase incarbon atoms of the alkyl chain of alkyl halide. The nitriles obtained undergo hydrolysis reaction in presence of acid and gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  5

The hydrolysis reaction of alkyl nitrile in presence of acid is written as:

Essential Organic Chemistry, Global Edition, Chapter 11.13, Problem 25P , additional homework tip  6

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Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution? a. butyric acid b. isovaleric acid c. cyclohexanecarboxylic acid
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What reagents/conditions would you use to convert a Alkyl Benzene to a carboxylic acid?

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