ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Chapter 10.7, Problem 14P
Interpretation Introduction

Interpretation:

The reason behind ‘'replacing HBr by HI in the third step of the synthesis shown would not provide a suitable synthesis for 1-iodo-2,3,3-trimethylbutane 'is to be explained and the synthesis is to be extended by an addition step to give the corresponding iodide.

Concept Introduction:

>

Addition of HBr to alkenes in the presence of peroxides takes place through the formation of alkyl free radicals.

>

The regioselectivity of addition is opposite to that of Markovnikov's rule.

>

Hydrogen chloride and hydrogen iodide do not add by a free radical mechanism when peroxides are present.

>

Reaction of primary alkyl bromides with sodium iodide in acetone replaces the bromine by iodine through SN2 mechanism.

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