Chapter 17, Problem 17.6P

Interpretation Introduction

(a)

Interpretation:

The product obtained from the reaction of cyclohexene with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is to be stated.

Concept introduction:

NBS stand for $N\text{-bromosuccinimide}$. $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. When a compound having allylic hydrogen is treated with $N\text{-bromosuccinimide}$ in presence of ${\text{CCl}}_{\text{4}}$, allylic bromination takes place.

Answer to Problem 17.6P

The product obtained from the reaction of cyclohexene with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{3-bromocyclohexene}$.

Explanation of Solution

It is known that the $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. Therefore, the bromination will take place at allylic carbon of cyclohexene. The reaction of cyclohexene with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is shown below.

Figure 1

Conclusion

The product obtained from the reaction of cyclohexene with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{3-bromocyclohexene}$.

Interpretation Introduction

(b)

Interpretation:

The products obtained from the reaction of $\text{3, 3-dimethylcyclohexene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides are to be stated.

Concept introduction:

NBS stand for the $N\text{-bromosuccinimide}$. $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. When a compound having allylic hydrogen is treated with $N\text{-bromosuccinimide}$ in presence of ${\text{CCl}}_{\text{4}}$, allylic bromination takes place.

Answer to Problem 17.6P

The product obtained from the reaction of $\text{3, 3-dimethylcyclohexene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{6-bromo-3, 3-dimethylcyclohexene}$.

Explanation of Solution

It is known that the $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. Therefore, the bromination will take place at allylic carbon of $\text{3, 3-dimethylcyclohexene}$. The reaction of $\text{3, 3-dimethylcyclohexene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is shown below.

Figure 2

Conclusion

The product obtained from the reaction of $\text{3, 3-dimethylcyclohexene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{6-bromo-3, 3-dimethylcyclohexene}$.

(c)

Interpretation Introduction

Interpretation:

The products obtained from the reaction of $trans\text{-2-pentene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides are to be stated.

Concept introduction:

NBS stand for the $N\text{-bromosuccinimide}$. $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. When a compound having allylic hydrogen is treated with $N\text{-bromosuccinimide}$ in presence of ${\text{CCl}}_{\text{4}}$, allylic bromination takes place.

Answer to Problem 17.6P

The products obtained from the reaction of $trans\text{-2-pentene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides are $\text{1-bromopent-2-ene}$ and $\text{4-bromopent-2-ene}$.

Explanation of Solution

It is known that the $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. Therefore, the bromination will take place at allylic carbon of $trans\text{-2-pentene}$. The reaction of $trans\text{-2-pentene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is shown below.

Figure 3

Conclusion

The products obtained from the reaction of $trans\text{-2-pentene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides are $\text{1-bromopent-2-ene}$ and $\text{4-bromopent-2-ene}$.

Interpretation Introduction

(d)

Interpretation:

The product obtained from the reaction of $\text{4-}tert\text{-butyltoluene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is to be stated.

Concept introduction:

NBS stand for the $N\text{-bromosuccinimide}$. $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. When a compound having allylic hydrogen is treated with $N\text{-bromosuccinimide}$ in presence of ${\text{CCl}}_{\text{4}}$, allylic bromination takes place.

Answer to Problem 17.6P

The product obtained from the reaction of $\text{4-}tert\text{-butyltoluene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{1-}tert\text{-butyl-4-}\left(\text{bromomethyl}\right)\text{benzene}$.

Explanation of Solution

It is known that the $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. Therefore, the bromination will take place at allylic carbon of $\text{4-}tert\text{-butyltoluene}$. The reaction of $\text{4-}tert\text{-butyltoluene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is shown below.

Figure 4

Conclusion

The product obtained from the reaction of $\text{4-}tert\text{-butyltoluene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{1-}tert\text{-butyl-4-}\left(\text{bromomethyl}\right)\text{benzene}$.

Interpretation Introduction

(e)

Interpretation:

The product obtained from the reaction of $\text{l-isopropyl-4-nitrobenzene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is to be stated.

Concept introduction:

NBS stand for the $N\text{-bromosuccinimide}$. $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. When a compound having allylic hydrogen is treated with $N\text{-bromosuccinimide}$ in presence of ${\text{CCl}}_{\text{4}}$, allylic bromination takes place.

Answer to Problem 17.6P

The product obtained from the reaction of $\text{l-isopropyl-4-nitrobenzene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{1-}\left(\text{2-bromopropan-2-yl}\right)\text{-4-nitrobenzene}$.

Explanation of Solution

It is known that the $N\text{-bromosuccinimide}$ is used for the bromination of allylic carbon. Therefore, the bromination will take place at allylic carbon of $\text{l-isopropyl-4-nitrobenzene}$. The reaction of $\text{l-isopropyl-4-nitrobenzene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is shown below.

Figure 5

Conclusion

The product obtained from the reaction of $\text{l-isopropyl-4-nitrobenzene}$ with one equivalent of NBS in ${\text{CCl}}_{\text{4}}$ in the presence of light and peroxides is $\text{1-}\left(\text{2-bromopropan-2-yl}\right)\text{-4-nitrobenzene}$.