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Chapter 10: PROBLEM 10.70 (page 425)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Step by step solution

01

Dehydration

The dehydration process occurs when the alcohol substrate undergoes acidification. In this, the oxygen of the -OH group attracts the proton from the acid and leaves as water.

02

Nucleophile

Alkenes also act as nucleophiles in the dehydration process. They form a bond by donating electrons to the carbocation.

03

Explanation

In the given reaction, the OH group accepts the proton of sulfuric acid. And therefore, a water molecule is eliminated.

After the elimination, a secondary carbocation is generated that undergoes 1, 2-hydrogen shift to form a more stable tertiary carbocation. Further, the alkene donates electrons to the tertiary carbocation and forms a cyclic compound.

The mechanism is shown below:

Dehydration

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Most popular questions from this chapter

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

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