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 S N 2 mechanism.

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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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