Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 19, Problem 19.32P

(a)

Interpretation Introduction

Interpretation:

Structural formula for the saponification acidification and decarboxylation product of β-ketoester diethyl 2-methyl-3-oxosuccinate has to be drawn.

Concept Introduction:

Saponification:

It is a process in which triglycerides reacts with sodium or potassium hydroxide to form fatty acids and glycerol.  This reaction is also known as alkaline hydrolysis of ester.

Decarboxylation:

It is a reaction which involves the release of carbondioxide by removing the carboxyl group.  This also involves the removal of carbon atom from the chain.

(b)

Interpretation Introduction

Interpretation:

Structural formula for the saponification acidification and decarboxylation product of β-ketoester ethyl 2-methyl-3-oxo-3-phenylpropanoate has to be drawn.

Concept Introduction:

Saponification:

It is a process in which triglycerides reacts with sodium or potassium hydroxide to form fatty acids and glycerol.  This reaction is also known as alkaline hydrolysis of ester.  Saponification is mainly used for manufacturing soap.

Decarboxylation:

It is a reaction which involves the release of carbondioxide by removing the carboxyl group.  This also involes the removal of carbon atom from the carbonchain.  Enzymes which catalyze decarboxylation are known as decarboxylase.  Alkanoic acid decarboxylation is very slow.

(c)

Interpretation Introduction

Interpretation:

Structural formula for the saponification acidification and decarboxylation product of ethyl 2-methyl-3-oxopropanoate has to be drawn.

Concept Introduction:

Saponification:

It is a process in which triglycerides reacts with sodium or potassium hydroxide to form fatty acids and glycerol.  In simple saponification is a reaction between an acid and a base to form salt.  The base commonly used is sodium hydroxide.  Potassium hydroxide is also used.  This reaction is also known as alkaline hydrolysis of ester.

Decarboxylation:

It is a reaction which erases a carbon atom from the carbon chain by releasing carbondioxide.  It is a unimolecular dissociative process that gives a carbanion and carbondioxide.

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Chapter 19 Solutions

Organic Chemistry

Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
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