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Which compound in each of the following pairs will react faster in an S N 2 reaction with OH - ? (a) CH 3 Br or CH 3 I (b) CH 3 CH 2 I in ethanol or in dimethyl sulfoxide (c) (CH 3 ) 3 CCl or CH 3 Cl (d) H 2 C=CHBr or H 2 C=CHCH 2 Br

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 11.SE, Problem 41AP
Textbook Problem
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Which compound in each of the following pairs will react faster in an SN2 reaction with OH-?

(a) CH3Br or CH3I

(b) CH3CH2I in ethanol or in dimethyl sulfoxide

(c) (CH3)3CCl or CH3Cl

(d) H2C=CHBr or H2C=CHCH2Br

Interpretation Introduction

Interpretation:

The faster reactant is to be identified from SN2 reaction with OH-.

Concept introduction:

SN2 reaction:

Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Organic Chemistry, Chapter 11.SE, Problem 41AP

Given information:

a.

The given compound is shown below,

CH3I and CH3Br

b.

The given compound is shown below,

CH3CH2I in ethanol and CH3CH2I in dim ethylsulf oxide (DMSO)

c.

The given compound is shown below,

(CH3)3CCl and CH3Cl

d.

The given compound is shown below,

CH2 = CH2 Br or CH2 = CHCH2Br

Explanation of Solution

a.

The given compound is shown below,

CH3I and CH3Br

Methyl iodide is undergoing SN2 very faster because, iodine is good leaving group than bromine.

b.

The given compound is shown below,

CH3CH2I in ethanol and CH3CH2I in dim ethylsulfoxide (DMSO)

ethyl iodide in dimethyl sulfoxide is undergoes SN2 very faster than ethyl iodide in ethanol because hydroxide ion may form hydrogen bonding with protic solvent ethanol. Therefore, the reaction is slow.

c...

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