8th Edition

ISBN: 9781305580350

Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher: Cengage Learning

Concept explainers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and…

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic…

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction…

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Textbook Question

Chapter 21, Problem 21.48P

In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents.

Chapter 21, Problem 21.48P, In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl , example 1

Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid.

Chapter 21, Problem 21.48P, In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl , example 2

(a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid?
(b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?

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Chapter 21, Problem 21.47P

Chapter 21, Problem 21.49P

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Chapter 21 Solutions

Organic Chemistry

Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3P Ch. 21.2 - Prob. 21.4P Ch. 21.3 - Prob. 21.5P Ch. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQ Ch. 21.4 - Prob. BQ Ch. 21.4 - Prob. CQ Ch. 21.5 - Prob. 21.7P

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Solution Summary: The author explains how the structure of the triphenylmethyl group should be modified to increase (or) decrease it's acid sensitivity.

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