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Chapter 18: Q42E (page 594)

Question: tert-Butyl ethers can be prepared by the reaction of an alcohol with2-methylpropene in the presence of an acid catalyst. Propose a mechanismfor this reaction

Short Answer

Expert verified

Protonation is defined as the addition of a proton to an atom, molecule or ion. It is different from hydrogenation because in protonation a change in charge of protonated species occurs, while the charge remain unaffected during hydrogenation. For example formation of ammonium groupfrom ammonia. Protonation is mainly occur in the reaction of an acid with a base to form salt.

Step by step solution

01

Protonation

Protonation is defined as the addition of a proton to an atom, molecule or ion. It is different from hydrogenation because in protonation a change in charge of protonated species occurs, while the charge remain unaffected during hydrogenation. For example formation of ammonium groupfrom ammonia. Protonation is mainly occur in the reaction of an acid with a base to form salt.

02

Protonation of 2-methyl propene

The first step of the reaction is protonation where 2-methylpropene gets protonated with acid to form tertiary carbocation as shown below:

Protonation of 2-methyl propene by acid

03

Attack on carbocation

In the second step of the reaction oxygen from ROH group attack on carbocation and make bond with the carbon by acquiring positive charge from the carbocation as shown below:

Attack of alcohol oxygen on carbocation

04

Loss of proton

In last step of the mechanism deprotonation occurs, tert-butyl ether is formed by the loss of proton.

Formation of tert-butyl ether

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