Chapter 11, Problem 11.33P

Interpretation Introduction

(a)

Interpretation:

The reaction with detailed mechanism for the formation of the given compound from the corresponding alkene by single electrophilic addition reaction is to be drawn.

Concept introduction:

The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The electrophilic addition of water across the double bond in an acidic condition produces the alcohol product. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile.

Answer to Problem 11.33P

The reaction equation and the detailed mechanism for the formation of $\text{pentan-2-ol}$ from alkene are

Explanation of Solution

The structure for the given compound $\text{pentan-2-ol}$ is

To form the given alcohol by electrophilic addition of water, the double bond must be between the carbon where the $\text{OH}$ group is attached and the adjacent methyl carbon in the substrate.

The reaction occurs in acidic condition. Thus the first step is the formation of a secondary carbocation by proton transfer reaction. The proton transfers to the less substituted carbon, forming a more stable carbocation.

In the second step, the water molecule acts as a nucleophile and attacks the carbocation, forming the desired product, followed by deprotonation of the positively charged oxygen.

Conclusion

The reaction equation and detailed mechanism are drawn for the formation of $\text{pentan-2-ol}$ by identifying the corresponding alkene.

Interpretation Introduction

(b)

Interpretation:

The reaction with detailed mechanism for the formation of the given compound from the corresponding alkene by single electrophilic addition reaction is to be drawn.

Concept introduction:

The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The electrophilic addition of water across the double bond in an acidic condition produces the alcohol product. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile.

Answer to Problem 11.33P

The reaction equation and the detailed mechanism for the formation of $\text{3-methylpentan-3-ol}$ from alkene are

Explanation of Solution

The structure for the given compound $\text{3-methylpentan-3-ol}$ is

To form the given alcohol by electrophilic addition of water, the double bond must be between the carbon where the $\text{OH}$ group is attached and the adjacent carbon in the substrate.

The reaction occurs in acidic condition. Thus the first step is the formation of a tertiary carbocation by proton transfer reaction. The proton transfers to the less substituted carbon, forming a more stable carbocation.

In the second step, the water molecule acts as a nucleophile and attacks the carbocation, forming the desired product, followed by deprotonation of the positively charged oxygen.

Conclusion

The reaction equation and detailed mechanism are drawn for the formation of $\text{3-methylpentan-3-ol}$ by identifying the corresponding alkene.

Interpretation Introduction

(c)

Interpretation:

The reaction with detailed mechanism for the formation of the given compound from the corresponding alkene by single electrophilic addition reaction is to be drawn.

Concept introduction:

The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The electrophilic addition of water across the double bond in an acidic condition produces the alcohol product. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile.

Answer to Problem 11.33P

The reaction equation and the detailed mechanism for the formation of $\text{1-methoxy-1, 4-dimethylcyclohexane}$ from alkene are

Explanation of Solution

The structure for the given compound $\text{1-methoxy-1, 4-dimethylcyclohexane}$ is

To form the given ether by electrophilic addition of alcohol, the double bond must be between the carbon where the ${\text{OCH}}_{\text{3}}$ group is attached and the adjacent carbon in the substrate.

The reaction occurs in acidic condition. Thus the first step is the formation of a tertiary carbocation by proton transfer reaction. The proton transfers to the less substituted carbon, forming a more stable carbocation.

In the second step, the methanol molecule acts as a nucleophile and attacks the carbocation, forming the desired product, followed by deprotonation of the positively charged oxygen.

Conclusion

The reaction equation and detailed mechanism are drawn for the formation of $\text{1-methoxy-1, 4-dimethylcyclohexane}$ by identifying the corresponding alkene.

Interpretation Introduction

(d)

Interpretation:

The reaction with detailed mechanism for the formation of the given compound from the corresponding alkene by single electrophilic addition reaction is to be drawn.

Concept introduction:

The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The electrophilic addition of water across the double bond in an acidic condition produces the alcohol product. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile.

Answer to Problem 11.33P

The reaction equation and the detailed mechanism for the formation of (cyclopentyldimethoxymethyl) benzene from alkene are

Explanation of Solution

The structure for the given compound (cyclopentyldimethoxymethyl) benzene is

To form the given ether by single electrophilic addition of alcohol, the double bond must be between the carbon where the ${\text{OCH}}_{\text{3}}$ group is attached and the adjacent carbon of the cyclopentyl ring in the substrate.

The reaction occurs in acidic condition. Thus the first step is the formation of a tertiary carbocation by proton transfer reaction. The proton transfers to the less substituted carbon, forming a more stable carbocation.

In the second step, the methanol molecule acts as a nucleophile and attacks the carbocation, forming the desired product, followed by deprotonation of the positively charged oxygen.

Conclusion

The reaction equation and detailed mechanism are drawn for the formation of (cyclopentyldimethoxymethyl) benzene by identifying the corresponding alkene.