ORGANIC CHEMISTRY-OWL V2 ACCESS
ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
Question
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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 βketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  1

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.

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  2

Decarboxylation of βketoacid is shown below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  3

The mechanism of thermal decarboxylation involves two processes,

  1. (i) Redistribution of electrons in a cyclic transition state.
  2. (ii) Cyclic transition state possesses keto-enol tautomerism.

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  4

(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 βketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  5

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.

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  6

Decarboxylation of βketoacid is shown below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  7

Simply the mechanism of thermal decarboxylation involves two processes,

  1. (i) Redistribution of electrons in a cyclic transition state.
  2. (ii) Cyclic transition state possesses keto-enol tautomerism.

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 17, Problem 17.41P , additional homework tip  8

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Chapter 17 Solutions

ORGANIC CHEMISTRY-OWL V2 ACCESS

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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