ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 8.4, Problem 11P
Interpretation Introduction

(a)

Interpretation: The change in the rate of an E2 reaction is to be stated when the concentration of alkyl halide is tripled.

Concept introduction: E2 type of reaction follows second order kinetics in which the rate depends on both the reactants. The rate law equation for E2 reaction is expressed as,

Rate=k[RX][B:]

Interpretation Introduction

(b)

Interpretation: The change in the rate of an E2 reaction is to be stated when the concentration of base is halved.

Concept introduction: E2 type of reaction follows second order kinetics in which the rate depends on both the reactants. The rate law equation for E2 reaction is expressed as,

Rate=k[RX][B:]

Interpretation Introduction

(c)

Interpretation: The change in the rate of an E2 reaction is to be stated when the solvent is changed from CH3OH to DMSO

Concept introduction: E2 reactions are usually preferred in polar aprotic solvents as the transition state involves charge dispersion which is stabilized by polar aprotic solvents.

Interpretation Introduction

(d)

Interpretation: The change in the rate of an E2 reaction is to be stated when the leaving is changed from I- to Br-

Concept introduction: A leaving group bigger in size is preferred as it leaves easily and fast while a smaller leaving group leaves with difficulty and slow.

Interpretation Introduction

(e)

Interpretation: The change in the rate of an E2 reaction is to be stated when the base is changed from OH- to H2O

Concept introduction: Strong base is more efficient in proton abstraction and hence, it is more preferred in E2 type of reactions.

Interpretation Introduction

(f)

Interpretation: The change in the rate of an E2 reaction is to be stated when the the alkyl halide is changed from CH3CH2Br to (CH3)2CHBr.

Concept introduction: The rate of E2 reaction depends on the halide being used. A halide in which carbon attached to the leaving group has more number of alkyl groups is usually preferred.

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How does each of the following changes affect the rate of an E2 reaction? a. tripling [RX] b. halving [B:] c. changing the solvent from CH3OH to DMSO d. changing the leaving group from I− to Br e. changing the base from −OH to H2O f. changing the alkyl halide from CH3CH2Br to (CH3)2CHBr
How does each of the following changes affect the rate of an E2 reaction? a.tripling [RX] b.halving [B:] c. changing the solvent from CH3OH to DMSO d.changing the leaving group from I− to Br− e. changing the base from −OH to H2O f.changing the alkyl halide from CH3CH2Br to (CH3)2CHBr
6. Predict the reactant (starting material) for the reaction and propose a mechanism. NaCN SN2 NaOH E2 CN a Ph Ph

Chapter 8 Solutions

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