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Predict the products of the sulfuric acid-catalyzed

Chapter 3, Problem 22P

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QUESTION:

Problem 22P

Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.

(a) 2-methylbutan-2-ol

(b) pentan-1-ol

(c) pentan-2-ol

(d) 1-isopropylcyclohexanol

(e) 2-methylcyclohexanol

Questions & Answers

QUESTION:

Problem 22P

Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.

(a) 2-methylbutan-2-ol

(b) pentan-1-ol

(c) pentan-2-ol

(d) 1-isopropylcyclohexanol

(e) 2-methylcyclohexanol

ANSWER:

Solution 22P

(a)

Treatment of 2-methylbutan-2-ol with sulfuric acid gives two possible alkenes, in which one is major (more substituted alkene) and the other is minor (less substituted alkene). Thus, the reaction is as follows:

(b)

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