Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 32P
Interpretation Introduction

Interpretation:

The reason behind the hydrolysis of methyl bromide taking place much faster in the presence of sodium iodide is to be explained.

Concept introduction:

The SN2 reaction is bimolecular nucleophilic substitution reaction, which means two components are involved in the rate determining step.

In the rate determining step, nucleophile approaches the carbon from the side directly opposite to the leaving group.

The SN2 reaction is a concerted reaction as bond formation and bond breaking occur in the same step.

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Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:
Suggest a reasonable mechanism for the reaction shown Br here. HO CH;CH,OH
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