Chapter 7.11, Problem 39ATS

(a)

Interpretation Introduction

Interpretation:

The structures of compound A should be predicted from the given molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{9}}\text{Cl}$, corresponding to given reaction condition.

Concept introduction:

• Highly polarizable reagents are considered as strong nucleophiles if the conjugate acid of the nucleophile has little nature then those nucleophiles considered as weak bases too. If the reagent is not polarizable and has basic nature, then the reagent is considered as strong base.
• Reaction mechanism path is depending on both natures of substrate and reagent.
• If the reagent is strong base as well as strong nucleophile and the substrate is primary alkyl halide then the reaction follows ${\text{S}}_{\text{N}}\text{2}$ mechanism if the substrate is secondary alkyl halide then the reaction follows $E2$ mechanism. For ${\text{S}}_{\text{N}}\text{2}$ mechanism reagent should be strong nucleophile.
• If the substrate is tertiary alkyl halide, then the reaction follows ${\text{S}}_{\text{N}}\text{1}$ mechanism rather than ${\text{S}}_{\text{N}}2$ mechanism. (when the reagent is strong nucleophile)
• If the reagent is strong bulky base, then the reaction follows E2 mechanism. For E2 reaction, reagent should be strong base.
• Constitutional isomers are isomers which have same molecular formula and different bond connectivity.

(b).

Interpretation Introduction

Interpretation:

The structures of compound B should be predicted from the given molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{9}}\text{Cl}$, corresponding to given reaction condition.

Concept introduction:

• Highly polarizable reagents are considered as strong nucleophiles if the conjugate acid of the nucleophile has little nature then those nucleophiles considered as weak bases too. If the reagent is not polarizable and has basic nature, then the reagent is considered as strong base.
• Reaction mechanism path is depending on both natures of substrate and reagent.
• If the reagent is strong base as well as strong nucleophile and the substrate is primary alkyl halide then the reaction follows ${\text{S}}_{\text{N}}\text{2}$ mechanism if the substrate is secondary alkyl halide then the reaction follows $E2$ mechanism. For ${\text{S}}_{\text{N}}\text{2}$ mechanism reagent should be strong nucleophile.
• If the substrate is tertiary alkyl halide, then the reaction follows ${\text{S}}_{\text{N}}\text{1}$ mechanism rather than ${\text{S}}_{\text{N}}2$ mechanism. (when the reagent is strong nucleophile)
• If the reagent is strong bulky base, then the reaction follows E2 mechanism. For E2 reaction, reagent should be strong base.
• Constitutional isomers are isomers which have same molecular formula and different bond connectivity.