Pearson eText Organic Chemistry -- Instant Access (Pearson+)

9th Edition

ISBN: 9780135213728

Author: Leroy Wade, Jan Simek

Publisher: PEARSON+

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Textbook Question

Chapter 20.10, Problem 20.14P

A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

a. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
b. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
c. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxyl oxygen.

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Chapter 20.10, Problem 20.13P

Chapter 20.10, Problem 20.15P

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Chapter 20 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

Ch. 20.2C - Prob. 20.1P Ch. 20.2C - Name the following carboxylic acids (when...Ch. 20.4B - Rank the compounds in each set in order of...Ch. 20.5 - Prob. 20.4P Ch. 20.5 - Phenols are less acidic than carboxylic acids,...Ch. 20.5 - Prob. 20.6P Ch. 20.7A - Prob. 20.7P Ch. 20.7B - Prob. 20.8P Ch. 20.7D - Draw all four resonance forms of the fragment at...Ch. 20.7D - a. Why do most long-chain fatty acids show a large...

Ch. 20.10 - Prob. 20.13P Ch. 20.10 - A carboxylic acid has two oxygen atoms, each with...Ch. 20.10 - Prob. 20.15P Ch. 20.10 - The mechanism of the Fischer esterification was...Ch. 20.10 - Prob. 20.17P Ch. 20.12 - Show how to synthesize the following compounds,...Ch. 20.13 - Show how you would synthesize the following...Ch. 20.14 - Prob. 20.20P Ch. 20.14 - Prob. 20.21P Ch. 20.15 - Propose a mechanism for the reaction of benzoic...Ch. 20.15 - Prob. 20.23P Ch. 20.15 - Prob. 20.24P Ch. 20 - Prob. 20.25SP Ch. 20 - Give both IUPAC names and common names for the...Ch. 20 - Draw the structures of the following compounds. a....Ch. 20 - Prob. 20.28SP Ch. 20 - Arrange each group of compounds in order of...Ch. 20 - Predict the products (if any) of the following...Ch. 20 - Rank the following isomers in order of increasing...Ch. 20 - Prob. 20.32SP Ch. 20 - What do the following pKa values tell you about...Ch. 20 - Given the structure of ascorbic acid (vitamin C):...Ch. 20 - Prob. 20.35SP Ch. 20 - Show how you would accomplish the following...Ch. 20 - Predict the products and propose mechanisms for...Ch. 20 - Prob. 20.38SP Ch. 20 - Prob. 20.39SP Ch. 20 - Prob. 20.40SP Ch. 20 - Prob. 20.44SP Ch. 20 - Prob. 20.45SP Ch. 20 - Predict the major form of each compound when it is...

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Solution Summary: The author compares the resonance forms of a carboxylic acid protonated on the hydroxy oxygen atom with those given previously.

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