Chapter 15, Problem 15.41P

Interpretation Introduction

(a)

Interpretation: The products for radical chlorination and bromination of given compound are to be drawn. The compounds which form single constitutional isomer for both reactions are to be predicted. The true structure of a reactant for both reactions to form a single product is to be identified.

Concept introduction: Chlorination and bromination are radical substitution reaction. In the reaction of chlorination, $\text{Cl}$ replaces hydrogen atom and forms alkyl halide in the presence of light. Similarly, in the bromination, an alkyl halide is formed by the replacement of hydrogen atom from highly substituted carbon by $\text{Br}$. Bromination is highly specific reaction than chlorination. Constitutional isomers have same molecular formula but they differ in the connectivity of substituents.

Answer to Problem 15.41P

The products of radical chlorination and bromination of given compound are,

A single constitutional isomer is formed for both reactions.

Explanation of Solution

Alkanes undergo chlorination when they are treated with ${\text{Cl}}_{\text{2}}$ in the presence of light. Chlorination can take place at primary, secondary and tertiary carbon atom. The product formed by the chlorination of given compound is shown in Figure 1.

Figure 1

Alkanes undergo bromination through free radical mechanism when they are treated with ${\text{Br}}_{\text{2}}$ in the presence of light. Bromination can take place at primary, secondary and tertiary carbon atom. The product formed by the bromination of given compound is shown in Figure 2.

Figure 2

A single constitutional isomer is formed for both reaction because all hydrogen atoms of given compound are present in a same chemical environment. Therefore, to form a single product, the chemical environment of hydrogen atoms should be same.

Conclusion

The products of radical chlorination and bromination of given compound are shown in Figure 1 and Figure 2, respectively. A single constitutional isomer is formed for both reactions.

Interpretation Introduction

(b)

Interpretation: The products for radical chlorination and bromination of given compound are to be drawn. The compounds which form single constitutional isomer for both reactions are to be predicted. The true structure of a reactant for both reactions to form a single product is to be identified.

Concept introduction: Chlorination and bromination are radical substitution reaction. In the reaction of chlorination, $\text{Cl}$ replaces hydrogen atom and forms alkyl halide in the presence of light. Similarly, in the bromination, an alkyl halide is formed by the replacement of hydrogen atom from highly substituted carbon by $\text{Br}$. Bromination is highly specific reaction than chlorination. Constitutional isomers have same molecular formula but they differ in the connectivity of substituents.

Answer to Problem 15.41P

The products of radical chlorination and bromination of given compound are,

A single constitutional isomer is not formed for both reactions.

Explanation of Solution

Alkanes undergo chlorination when they are treated with ${\text{Cl}}_{\text{2}}$ in the presence of light. Chlorination can take place at primary, secondary and tertiary carbon atom. The products formed by the chlorination of given compound are shown in Figure 3.

Figure 3

Alkanes undergo bromination by free radical mechanism when they are treated with ${\text{Br}}_{\text{2}}$ in the presence of light. Bromination can take place at primary, secondary and tertiary carbon atom. However, the bromination is more selective than chlorination. Hence, tertiary product is more favorable than secondary or primary. The product formed by the bromination of given compound is shown in Figure 4.

Figure 4

A single constitutional isomer is formed for bromination reaction but not for chlorination because bromine is more selective than chlorine.

Conclusion

The products of radical chlorination and bromination of given compound are shown in Figure 3 and Figure 4, respectively. A single constitutional isomer is not formed for both reactions.

Interpretation Introduction

(c)

Interpretation: The products for radical chlorination and bromination of given compound are to be drawn. The compounds which form single constitutional isomer for both reactions are to be predicted. The true structure of a reactant for both reactions to form a single product is to be identified.

Concept introduction: Chlorination and bromination are radical substitution reaction. In the reaction of chlorination, $\text{Cl}$ replaces hydrogen atom and forms alkyl halide in the presence of light. Similarly, in the bromination, an alkyl halide is formed by the replacement of hydrogen atom from highly substituted carbon by $\text{Br}$. Bromination is highly specific reaction than chlorination. Constitutional isomers have same molecular formula but they differ in the connectivity of substituents.

Answer to Problem 15.41P

The products of radical chlorination and bromination of given compound are,

A single constitutional isomer is formed for both reactions.

Explanation of Solution

Alkanes undergo chlorination when they are treated with ${\text{Cl}}_{\text{2}}$ in the presence of light. Chlorination can take place at primary, secondary and tertiary carbon atom. The product formed by the chlorination of given compound is shown in Figure 2.

Figure 5

Alkanes undergo bromination when they are treated with ${\text{Br}}_{\text{2}}$ in the presence of light. Bromination can take place at primary, secondary and tertiary carbon atom. The product formed by the bromination of given compound is shown in Figure 6.

Figure 6

A single constitutional isomer is formed for both reaction because all hydrogen atoms of given compound are present in same chemical environment. Therefore, to form a single product, the chemical environment of hydrogen atoms should be same.

Conclusion

The products of radical chlorination and bromination of given compound are shown in Figure 5 and Figure 6, respectively. A single constitutional isomer is formed for both reactions.

Interpretation Introduction

(d)

Interpretation: The products for radical chlorination and bromination of given compound are to be drawn. The compounds which form single constitutional isomer for both reactions are to be predicted. The true structure of a reactant for both reactions to form a single product is to be identified.

Concept introduction: Chlorination and bromination are radical substitution reaction. In the reaction of chlorination, $\text{Cl}$ replaces hydrogen atom and forms alkyl halide in the presence of light. Similarly, in the bromination, an alkyl halide is formed by the replacement of hydrogen atom from highly substituted carbon by $\text{Br}$. Bromination is highly specific reaction than chlorination. Constitutional isomers have same molecular formula but they differ in the connectivity of substituents.

Answer to Problem 15.41P

The products of radical chlorination and bromination of given compound are,

A single constitutional isomer is formed for both reactions.

Explanation of Solution

Alkanes undergo chlorination when they are treated with ${\text{Cl}}_{\text{2}}$ in the presence of light. Chlorination can take place at primary, secondary and tertiary carbon atom. The product formed by the chlorination of given compound is shown in Figure 7.

Figure 7

Alkanes undergo bromination when they are treated with ${\text{Br}}_{\text{2}}$ in the presence of light. Bromination can take place at primary, secondary and tertiary carbon atom. The product formed by the bromination of given compound is shown in Figure 8.

Figure 8

A single constitutional isomer is formed for both reaction because all hydrogen atoms of given compound are present in same chemical environment. Therefore, to form a single product, the chemical environment of hydrogen atoms should be same.

Conclusion

The products of radical chlorination and bromination of given compound are shown in Figure 7 and Figure 8, respectively. A single constitutional isomer is formed for both reactions.

Interpretation Introduction

(e)

Interpretation: The products for radical chlorination and bromination of given compound are to be drawn. The compounds which form single constitutional isomer for both reactions are to be predicted. The true structure of a reactant for both reactions to form a single product is to be identified.

Concept introduction: Chlorination and bromination are radical substitution reaction. In the reaction of chlorination, $\text{Cl}$ replaces hydrogen atom and forms alkyl halide in the presence of light. Similarly, in the bromination, an alkyl halide is formed by the replacement of hydrogen atom from highly substituted carbon by $\text{Br}$. Bromination is highly specific reaction than chlorination. Constitutional isomers have same molecular formula but they differ in the connectivity of substituents.

Answer to Problem 15.41P

The products of radical chlorination and bromination of given compound are,

A single constitutional isomer is not formed for both reactions.

Explanation of Solution

Alkanes undergo chlorination when they are treated with ${\text{Cl}}_{\text{2}}$ in the presence of light. Chlorination can take place at primary, secondary and tertiary carbon atom. The product formed by the chlorination of given compound is shown in Figure 9.

Figure 9

Alkanes undergo bromination by free radical mechanism when they are treated with ${\text{Br}}_{\text{2}}$ in the presence of light. Bromination can take place at primary, secondary and tertiary carbon atom. However, the bromination is more selective than chlorination. Hence, tertiary product is more favorable than secondary or primary. The product formed by the bromination of given compound is shown in Figure 10.

Figure 10

A single constitutional isomer is formed for bromination reaction but not for chlorination because bromine is more selective than chlorine.

Conclusion

The products of radical chlorination and bromination of given compound are shown in Figure 9 and Figure 10, respectively. A single constitutional isomer is not formed for both reactions.