Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 17, Problem 17.41P
(a)
Interpretation Introduction
Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of
Concept introduction:
Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,
If
Decarboxylation of
The mechanism of thermal decarboxylation involves two processes,
- (i) Redistribution of electrons in a cyclic transition state.
- (ii) Cyclic transition state possesses keto-enol tautomerism.
(b)
Interpretation Introduction
Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of
Concept introduction:
Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,
If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.
Decarboxylation of
Simply the mechanism of thermal decarboxylation involves two processes,
- (i) Redistribution of electrons in a cyclic transition state.
- (ii) Cyclic transition state possesses keto-enol tautomerism.
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Chapter 17 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 17.2 - Prob. 17.1PCh. 17.4 - Which is the stronger acid in each pair?Ch. 17.4 - Prob. 17.3PCh. 17.7 - Prob. 17.4PCh. 17.8 - Prob. 17.5PCh. 17.8 - Prob. AQCh. 17.8 - Prob. BQCh. 17.8 - Prob. CQCh. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.9 - Prob. 17.6P
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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