Chapter 10, Problem 10.29P

Interpretation Introduction

(a)

Interpretation: The constitutional isomer formed by the reaction of given alkene with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is to be predicted.

Concept introduction: The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Answer to Problem 10.29P

The constitutional isomer formed by the reaction of given alkene with ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is,

Figure 1

The constitutional isomer formed by the reaction of given alkene with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is,

Figure 2

Explanation of Solution

The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows Anti-Markovnikov’s rule.

In hydration reactions, the mode of addition is anti-addition, whereas in hydroboration-oxidation, the mode of addition is syn addition.

The given alkene is,

Figure 3

The product formed by the reaction of methylenecyclopentane with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is shown below.

Figure 4

The general steps followed by the hydration reaction are stated below:

• First protonation of the alkene take place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

The product formed by the reaction of methylenecyclopentane with ${\text{H}}_{\text{2}}\text{O,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown below.

Figure 5

Conclusion

The constitutional isomer formed by the reaction of given alkenes with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is rightfully stated.

Interpretation Introduction

(b)

Interpretation: The constitutional isomer formed by the reaction of given alkenes with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is to be predicted.

Concept introduction: The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Answer to Problem 10.29P

The constitutional isomer formed by the reaction of given alkenes with ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is,

Figure 6

The constitutional isomer formed by the reaction of given alkenes with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is,

Figure 7

Explanation of Solution

The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows Anti-Markovnikov’s rule.

In hydration reactions, the mode of addition is anti-addition, whereas in hydroboration-oxidation, the mode of addition is syn addition.

The given alkene is,

Figure 8

The product formed by the reaction of $\text{prop}-1-\text{en}-2-\text{ylcyclhexane}$ with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is shown below.

Figure 9

The general steps followed by the hydration reaction are stated below:

• First protonation of the alkene take place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

The product formed by the reaction of $\text{prop}-1-\text{en}-2-\text{ylcyclhexane}$ with ${\text{H}}_{\text{2}}\text{O,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown below.

Figure 10

Conclusion

The constitutional isomer formed by the reaction of given alkenes with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is rightfully stated.

Interpretation Introduction

(c)

Interpretation: The constitutional isomer formed by the reaction of given alkene with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is to be predicted.

Concept introduction: The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Answer to Problem 10.29P

The constitutional isomer formed by the reaction of given alkene with ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is,

Figure 11

The constitutional isomer formed by the reaction of given alkene with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is,

Figure 12

Explanation of Solution

The compounds with same chemical formula but different arrangement of atoms in space are known as the constitutional isomer.

Hydration of alkenes is one of the methods used for the formation of alcohol.

Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows Anti-Markovnikov’s rule.

In hydration reactions, the mode of addition is anti-addition, whereas in hydroboration-oxidation, the mode of addition is syn addition.

The given alkene is,

Figure 13

The product formed by the reaction of methylenecyclopentane with ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is shown below.

Figure 14

The general steps followed by the hydration reaction are stated below:

• First protonation of the alkene take place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

The product formed by the reaction of methylenecyclopentane with ${\text{H}}_{\text{2}}\text{O,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is shown below.

Figure 15

Conclusion

The constitutional isomer formed by the reaction of given alkenes with [1] ${\text{H}}_{\text{2}}{\text{O, H}}_{\text{2}}{\text{SO}}_{\text{4}}$ and [2] ${\text{BH}}_{\text{3}}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ is rightfully stated.