Given reaction of 2-metylpropene with CH3OH in the presence of H2SO4 catalyst yields methyl tert- butylether, CH3OC(CH3)3, by a mechanism analogous to that of acid catalyzed alkene hydration. The mechanism for each step of the reaction is to be given using curved arrows. Concept introduction: In the presence of strong acids the double bond in alkene is protonated by the nucleophilic attack of the Ï€ electrons in double bond on the hydrogen of the acid. The carbonium ion obtained during the process is then attacked by the unshared pair of the electrons on oxygen in methanol to yield an intermediate which loses a proton to give the final ether as product. To give: The mechanism for each step of the reaction in which 2-metylpropene reacts with CH3OH in the presence of H2SO4 catalyst to yield methyl tert- butylether, CH3OC(CH3)3.

Question

5B In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 CH3 H3C-C H -Br CH3 EtOH

Answer 1

Question

Chapter 8.SE, Problem 33MP

Interpretation Introduction

Interpretation:

Given reaction of 2-metylpropene with CH3OH in the presence of H2SO4 catalyst yields methyl tert-butylether, CH3OC(CH3)3, by a mechanism analogous to that of acid catalyzed alkene hydration. The mechanism for each step of the reaction is to be given using curved arrows.

Concept introduction:

In the presence of strong acids the double bond in alkene is protonated by the nucleophilic attack of the Ï€ electrons in double bond on the hydrogen of the acid. The carbonium ion obtained during the process is then attacked by the unshared pair of the electrons on oxygen in methanol to yield an intermediate which loses a proton to give the final ether as product.

To give:

The mechanism for each step of the reaction in which 2-metylpropene reacts with CH3OH in the presence of H2SO4 catalyst to yield methyl tert-butylether, CH3OC(CH3)3.

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