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 17, Problem 17.15P

(a)

Interpretation Introduction

Interpretation:

The given set of compounds has to be arranged in the increasing order of boing point.

Concept introduction:

The boiling points of carboxylic acids are higher than those of alcohol or aldehydes of similar relative molecular mass due to intermolecular hydrogen bonding.

Intermolecular hydrogen bonding will increase the boiling point of an organic compound.

Carboxylic acids can form dimers in which hydrogen bonds form between two carboxyl groups this will also increase their boiling point.

Increasing order of boiling point of some organic compounds with similar molecular weight is shown below,

Alkane<Ether<Alkylhalide<Amine<Ketone,aldehyde<Alcohol<Carboxylicacid

The better hydrogen bond capability of a molecule will increase its boiling points.

(b)

Interpretation Introduction

Interpretation:

The given set of compounds has to be arranged in the increasing order of boing point.

Concept introduction:

The boiling points of carboxylic acids are higher than those of alcohol or aldehydes of similar relative molecular mass due to intermolecular hydrogen bonding.

Carboxylic acids can form dimers in which hydrogen bonds form between two carboxyl groups this will also increase their boiling point.

Intermolecular hydrogen bonding will increase the boiling point of an organic compound.

Increasing order of boiling point of some organic compounds with similar molecular weight is shown below,

Alkane<Ether<Alkylhalide<Amine<Ketone,aldehyde<Alcohol<Carboxylicacid

The better hydrogen bond capability of a molecule will increase its boiling points.

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Chapter 17 Solutions

Organic Chemistry

Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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