On reaction with HC1, one of the trimethylcyclohexanols shown below furnishes a single product; the other furnishes a mixture of two stereoisomers. Fully explain this observation and show which starting material (A or B) produces which product(s). ОН ОН А В

On reaction with HC1, one of the trimethylcyclohexanols shown below furnishes a single product; the other furnishes a mixture of two stereoisomers. Fully explain this observation and show which starting material (A or B) produces which product(s). ОН ОН А В

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

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.50P: Following is the structure of miconazole, the active antifungal agent in a number of...

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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

On reaction with HC1, one of the trimethylcyclohexanols shown below furnishes a single
product; the other furnishes a mixture of two stereoisomers. Fully explain this observation and show
which starting material (A or B) produces which product(s).
ОН
ОН
A
В

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