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Chapter 10: PROBLEM 10.70 (page 425)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

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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