ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 6, Problem 59P

(a)

Interpretation Introduction

Interpretation: Effect of change of substrate from CH3Cl to CH3I for the SN2 reaction of CH3Cl should be predicted.

Concept introduction: Bimolecular substitution or SN2 proceeds via single-step mechanism. Thus, it is well known as concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general SN2 reaction mechanistic pathway is illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 6, Problem 59P , additional homework tip  1

SN2 pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to inverted S stereoisomer and vice versa. Thus, the outcome is the rear side displacement of leaving group.

Polar-aprotic solvents accelerate the rate of SN2 reactions. These solvents possess partial positive and negative charges also. However, they do not liberate any proton to the substrate unlike water, methanol solvents. Acetone, DMSO, THF or DMF are categorized as polar aprotic solvent.

(b)

Interpretation Introduction

Interpretation:Effect of change of nucleophile from CH3O to CH3S for the SN2 reaction of CH3Cl should be predicted.

Concept introduction:Bimolecular substitution or SN2 proceeds via single-step mechanism. Thus, it is well known as concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general SN2 reaction mechanistic pathway is illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 6, Problem 59P , additional homework tip  2

SN2 pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to inverted S stereoisomer and vice versa. Thus, the outcome is the rear side displacement of leaving group.

Polar-aprotic solvents accelerate the rate of SN2 reactions. These solvents possess partial positive and negative charges also. However, they do not liberate any proton to the substrate unlike water, methanol solvents. Acetone, DMSO, THF or DMF are categorized as polar aprotic solvent.

(c)

Interpretation Introduction

Interpretation:: Effect of change of substrate from CH3Cl to ( CH3)2CHCl for the SN2 reaction of CH3Cl should be predicted.

Concept introduction:Bimolecular substitution or SN2 proceeds via single-step mechanism. Thus, it is well known as concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

(d)

Interpretation Introduction

Interpretation:Effect of change of solvent from CH3OH to ( CH3)2SO for the SN2 reaction of CH3Cl should be predicted.

Concept introduction: Bimolecular substitution or SN2 proceeds via single -step mechanism. Thus, it is well known as concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

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