Chapter 7, Problem 7.17P

Interpretation Introduction

(a)

Interpretation: The stronger nucleophile out of ${\text{Br}}^{-}$ and ${\text{Cl}}^{-}$ in a polar protic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative $\text{O}$ or $\text{N}$ atom is termed as polar protic solvent. The nucleophilicity of anion that has small size is higher than the anion that has larger size.

Interpretation Introduction

(b)

Interpretation: The stronger nucleophile out of ${\text{Br}}^{-}$ and ${\text{Cl}}^{-}$ in a polar aprotic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative $\text{O}$ or $\text{N}$ atom is termed as polar protic solvent. However, in polar aprotic solvent, $\text{O}-\text{H}$ bond or $\text{N}-\text{H}$ is absent.

Interpretation Introduction

(c)

Interpretation: The stronger nucleophile out of ${\text{HS}}^{-}$ and ${\text{F}}^{-}$ in a polar protic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative $\text{O}$ or $\text{N}$ atom is termed as polar protic solvent. The nucleophilicity of anion that has small size is higher than the anion that has larger size.