3. The solvolysis of 13-C is much more sensitive to aryl substituent effects than that of 13- D. Offer a mechanistic interpretation of the following observations. Ar- OPNB Ar OPNB p=-3.27 p=-5.27 13-C 13-D

3. The solvolysis of 13-C is much more sensitive to aryl substituent effects than that of 13- D. Offer a mechanistic interpretation of the following observations. Ar- OPNB Ar OPNB p=-3.27 p=-5.27 13-C 13-D

Organic Chemistry

8th Edition

ISBN:9781305580350

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

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.47P: When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and...

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Concept explainers

Reactions of Ethers

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 behavior of ethers are discussed in the context of organic chemistry.

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.

Question

3. The solvolysis of 13-C is much more sensitive to aryl substituent effects than that of 13-
D. Offer a mechanistic interpretation of the following observations.
Ar
- OPNB
Ar
OPNB
p=-5.27
p=-3.27
13-C
13-D

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