Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 18, Problem 18.24P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

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 gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  1

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

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  2

The amide is first formed when the cyano group is hydrolysed in excess of water and if there is only one mole of water per mole of nitrile, the reaction can be stopped by the formation of amide.

(b)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

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 gives carboxylic acid. The general reaction of alkyl halides and sodum cyanide is written as,

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  3

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

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  4

The amide is first formed when the cyano group is hydrolysed in excess of water and if there is only one mole of water per mole of nitrile, the reaction can be stopped by the formation of amide.

(c)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

Amide hydrolysis in aqueous base:

A carboxylate anion and ammonia or an amine will be the product of nitrile hydrolysis in aqueous base.

The formed carboxylate anion can be converted into carboxylic acid by the acidification of the reaction mixture.

(d)

Interpretation Introduction

The structural formula for the principal product formed when benzonitrile is treated with the given reagent has to be drawn.

Concept introduction:

Concept introduction:

LiAlH4 is a powerful reducing agent which reduces the cyano group of a nitrile to a primary amino group.

Organic Chemistry, Chapter 18, Problem 18.24P , additional homework tip  5

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Chapter 18 Solutions

Organic Chemistry

Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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