Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 22, Problem 57P
Interpretation Introduction
Interpretation: The stepwise mechanism for the conversion of A to B is to be drawn.
Concept introduction: The Aldol condensation reaction that takes place within the same molecule in presence of strong base is known as intramolecular aldol reactions. This reaction takes place within the dicarbonyl compounds in which one carbonyl group forms the enolate that acts as a nucleophile and reacts with second carbonyl group which acts as electrophile.
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Even though B contains three ester groups, a single Dieckmann product results when B is treated with NaOCH3 in CH3OH, followed by H3O+. Draw the structure and explain why it is the only product formed.
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Chapter 22 Solutions
Organic Chemistry (6th Edition)
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4PCh. 22.1 - Prob. 5PCh. 22.2 - Prob. 6PCh. 22.2 - Problem 24.7
Draw the products formed in each...Ch. 22.4 - Prob. 15PCh. 22.4 - Prob. 16PCh. 22.5 - Problem 24.16
What ester is formed when each...
Ch. 22.6 - Prob. 18PCh. 22.6 - Prob. 19PCh. 22.6 -
Draw the products of each reaction.
a. b.
Ch. 22.6 - Problem 24.20
Two steps in a synthesis of the...Ch. 22.7 - Prob. 22PCh. 22.8 - Problem 24.22
Which of the following compounds can...Ch. 22.8 - Prob. 24PCh. 22.8 - Problem 24.24
What starting materials are needed...Ch. 22 - Prob. 29PCh. 22 - 24.29 What steps are needed to convert A to B?
Ch. 22 - Prob. 31PCh. 22 - 24.31 Draw the product formed in each directed...Ch. 22 - Prob. 33PCh. 22 - 24.33 What starting materials are needed to...Ch. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - 24.36 Identify the structures of C and D in the...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - 24.39 Draw the product formed from a Claisen...Ch. 22 - Prob. 41PCh. 22 - 24.41 Even though B contains three ester groups, a...Ch. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - 24.44 Vetivone is isolated from vetiver, a...Ch. 22 - Draw the product of each Robinson annulation from...Ch. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - 24.52 Draw a stepwise mechanism for the following...Ch. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56PCh. 22 - Prob. 57PCh. 22 - Prob. 58PCh. 22 - Prob. 59PCh. 22 - 24.62 Devise a synthesis of each compound from ,...Ch. 22 - Prob. 63P
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