ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 7.5, Problem 7.9TIY

(a)

Interpretation Introduction

Interpretation: The expected product for the reactions is to be drawn and stereochemistry along with preferred substitution mechanistic pathway between SN1 and SN2 should be determined.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.5, Problem 7.9TIY , additional homework tip  1

Concept introduction: Unimolecuar substitution or SN1 proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

The general reaction mechanism for the SN1 reaction is given as follows:

Step 1: Formation of a carbocation.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.5, Problem 7.9TIY , additional homework tip  2

Step 2: Attack of a nucleophile on electron-deficient carbon of a carbocation.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.5, Problem 7.9TIY , additional homework tip  3

(b)

Interpretation Introduction

Interpretation: Whether treatment of R-2-chlorobutane with aqueous ammonia is a good synthetic method for the preparation of R-2-butanamine should be determined.

Concept introduction: It has been found experimentally that if the leaving group lies on tertiary carbon than reaction proceeds preferentially via SN1 while if the leaving group lies on primary carbon reaction proceeds preferentially via SN2 .

If the leaving group lies on secondary than both SN1 and SN2 mechanisms are probable. However in such cases the solvents govern the major pathway. For instance, with solvents such as DMF, acetone the SN2 reaction occurs with secondary alkyl halide. These solvents are commonly termed as polar aprotic solvents. With solvents such as methanol, water the SN1 reaction occurs with secondary alkyl halide. These are termed as polar protic solvents.

A good nucleophile can take part in both SN1 and SN2 . Strong nucleophiles are more favored to react via SN2 pathway, poor nucleophile are less favored for SN2 pathway.

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