Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 9, Problem 9.14P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(a)

Expert Solution
Check Mark

Answer to Problem 9.14P

In the given reaction, primary halide is a substrate so that the given reaction is undergoes SN2 reaction.

Explanation of Solution

Reactivity of alkyl halide in SN2 reaction is,

  1°>2°>3°

In the given reaction, primary halide is a substrate so the given reaction is undergoes SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(b)

Expert Solution
Check Mark

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 SN2 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 SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(c)

Expert Solution
Check Mark

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 SN2 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 SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(d)

Expert Solution
Check Mark

Answer to Problem 9.14P

In the given reaction, Methanethionate is a good nucleophile but weak base so that the given reaction undergoes SN2 reaction.

Explanation of Solution

In the given reaction, Methanethionate is a good nucleophile but weak base so that the given reaction undergoes SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(e)

Expert Solution
Check Mark

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide so that the given reaction undergoes SN2 reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide so that the given reaction undergoes SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(f)

Expert Solution
Check Mark

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 SN2 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 SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  6

(g)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(g)

Expert Solution
Check Mark

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 SN2 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 SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  7

(h)

Interpretation Introduction

Interpretation:

The structural formula for the product of given SN2 reaction has to be drawn.

Concept Introduction:

  • SN2 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.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.

(h)

Expert Solution
Check Mark

Answer to Problem 9.14P

In the given reaction, substrate is a primary halide so that the given reaction undergoes SN2 reaction.

Explanation of Solution

In the given reaction, substrate is a primary halide, acetone is polar aprotic solvent so that the given reaction undergoes SN2 reaction.

Organic Chemistry, Loose-leaf Version, Chapter 9, Problem 9.14P , additional homework tip  8

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Chapter 9 Solutions

Organic Chemistry, Loose-leaf Version

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