Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 18.10, Problem 18.10P

(a)

Interpretation Introduction

Interpretation:

The conversion of hexanoic acid to given amine has to be shown.

Concept introduction:

Acid chlorides are most often prepared by treating a carboxylic acid with thionyl chloride.

Organic Chemistry, Loose-leaf Version, Chapter 18.10, Problem 18.10P , additional homework tip  1

Reaction of acid chloride with ammonia or amines:

The reaction of acid chlorides with ammonia and primary and secondary amines will yield amide.

The nucleophilic addition of ammonia or amine to the carbonyl carbon occurs which is followed by a proton transfer forming an addition intermediate that will eliminate chloride and lose a proton to give the amide compound.

LiAlH4 is a powerful reducing agent which reduces carboxylic acids to primary alcohol.

Organic Chemistry, Loose-leaf Version, Chapter 18.10, Problem 18.10P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The conversion of hexanoic acid to given amine has to be shown.

Concept introduction:

Acid chlorides are most often prepared by treating a carboxylic acid with thionyl chloride.

Organic Chemistry, Loose-leaf Version, Chapter 18.10, Problem 18.10P , additional homework tip  3

Reaction of acid chloride with ammonia or amines:

The reaction of acid chlorides with ammonia and primary and secondary amines will yield amide.

The nucleophilic addition of ammonia or amine to the carbonyl carbon occurs which is followed by a proton transfer forming an addition intermediate that will eliminate chloride and lose a proton to give the amide compound.

LiAlH4 is a powerful reducing agent which reduces carboxylic acids to primary alcohol.

Organic Chemistry, Loose-leaf Version, Chapter 18.10, Problem 18.10P , additional homework tip  4

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Chapter 18 Solutions

Organic Chemistry, Loose-leaf Version

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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