Chapter 7, Problem 7.19P

Interpretation Introduction

(a)

Interpretation: The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.19P

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}\text{SH}$ or ${\text{H}}_{\text{2}}\text{S}$.

Explanation of Solution

The reactant of the reaction is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$. The structure of the product shows that $\text{SH}$ group is present at the place of $\text{Br}$ group. Hence, ${\text{Br}}^{-}$ acts as a leaving group and ${}^{-}\text{SH}$ or ${\text{H}}_{\text{2}}\text{S}$ acts as a nucleophile during the formation of product. The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${}^{-}\text{SH}$ is shown in Figure 1.

Figure 1

The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${\text{H}}_{\text{2}}\text{S}$ is shown in Figure 2.

Figure 2

Conclusion

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}\text{SH}$ or ${\text{H}}_{\text{2}}\text{S}$.

Interpretation Introduction

(b)

Interpretation: The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.19P

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ or ${\text{HOCH}}_{\text{2}}{\text{CH}}_{\text{3}}$.

Explanation of Solution

The reactant of the reaction is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$. The structure of the product shows that $-{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ group is present at the place of $\text{Br}$ group. Hence, ${\text{Br}}^{-}$ acts as a leaving group and ${}^{-}{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ or ${\text{HOCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ acts as a nucleophile during the formation of product. The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${}^{-}{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ is shown in Figure 3.

Figure 3

The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${\text{H}}_{\text{2}}\text{S}$ is shown in Figure 4.

Figure 4

Conclusion

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}{\text{OCH}}_{\text{2}}{\text{CH}}_{\text{3}}$ or ${\text{HOCH}}_{\text{2}}{\text{CH}}_{\text{3}}$.

Interpretation Introduction

(c)

Interpretation: The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.19P

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}{\text{OOCH}}_3$ or ${\text{HOOCH}}_{\text{3}}$.

Explanation of Solution

The reactant of the reaction is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$. The structure of the product shows that $-{\text{OOCH}}_3$ group is present at the place of $\text{Br}$ group. Hence, ${\text{Br}}^{-}$ acts as a leaving group and ${}^{-}{\text{OOCH}}_3$ or ${\text{HOOCH}}_{\text{3}}$ acts as a nucleophile during the formation of product. The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${}^{-}{\text{OOCH}}_3$ is shown in Figure 5.

Figure 5

The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${\text{H}}_{\text{2}}\text{S}$ is shown in Figure 6.

Figure 6

Conclusion

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}{\text{OOCH}}_3$ or ${\text{HOOCH}}_{\text{3}}$.

Interpretation Introduction

(d)

Interpretation: The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.19P

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}\text{CN}$.

Explanation of Solution

The reactant of the reaction is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$. The structure of the product shows that $-\text{CN}$ group is present at the place of $\text{Br}$ group. Hence, ${\text{Br}}^{-}$ acts as a leaving group and ${}^{-}\text{CN}$ acts as a nucleophile during the formation of product. The reaction of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ with ${}^{-}\text{CN}$ is shown in Figure 7.

Figure 7

Conclusion

The nucleophile needed to convert ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{Br}$ to given product is ${}^{-}\text{CN}$.