Chapter 9, Problem 9.14P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, primary halide is a substrate so that the given reaction is undergoes ${\text{S}}_{\text{N}}\text{2}$ reaction.

Explanation of Solution

Reactivity of alkyl halide in ${\text{S}}_{\text{N}}\text{2}$ reaction is,

  $1°>2°>3°$

In the given reaction, primary halide is a substrate so the given reaction is undergoes ${\text{S}}_{\text{N}}\text{2}$ reaction.

(b)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, Tri-methyl amine is a moderate nucleophile and acetone is a polar aprotic solvent and substrate is alkyl halide so that the given reaction is undergoes ${\text{S}}_{\text{N}}\text{2}$ reaction.

Explanation of Solution

In the given reaction, Tri-methyl amine is a moderate nucleophile and acetone is a polar aprotic solvent and substrate is alkyl halide so that the given reaction is undergoes ${\text{S}}_{\text{N}}\text{2}$ reaction.

(c)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide, acetone is polar aprotic solvent and cyanide is a good nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide, acetone is polar aprotic solvent and cyanide is a good nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

(d)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, Methanethionate is a good nucleophile but weak base so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, Methanethionate is a good nucleophile but weak base so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

(e)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

(f)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide and ammonia is a moderate nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide and ammonia is a moderate nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

(g)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide and Morpholine is a moderate nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide and Morpholine is a moderate nucleophile so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

(h)

Interpretation Introduction

Interpretation:

The structural formula for the product of given ${\text{S}}_{\text{N}}\text{2}$ reaction has to be drawn.

Concept Introduction:

• ${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
• $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$
• Structure of the substrate plays a major role in ${\text{S}}_{\text{N}}2$ reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of ${\text{S}}_{\text{N}}2$ reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
• Polar aprotic solvent is good for ${\text{S}}_{\text{N}}2$ reaction because it is not interact with nucleophile.
• Less basic good or moderate nucleophile is good for ${\text{S}}_{\text{N}}2$ reaction because it is not abstract a proton only attacks the positive center only.

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide, acetone is polar aprotic solvent so that the given reaction undergoes ${\text{S}}_{\text{N}}2$ reaction.