ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 6, Problem 57P

(a)

Interpretation Introduction

Interpretation: Nucleophile that is better suited for its role in SN2 reaction should be indicated.

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 57P , 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: Substrate that is better suited for its role in SN2 reaction should be indicated.

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 57P , 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: Solvent that is better suited for its role in SN2 reaction should be indicated.

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: Leaving group that is better suited for its role in SN2 reaction should be indicated.

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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