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The reaction of an alkyl chloride (or bromide) with sodium iodide in acetone proceeds ac...

The reaction of an alkyl chloride (or bromide) with sodium iodide in acetone proceeds according to the following equation:

Sodium iodide is soluble in acetone, whereas both sodium chloride and sodium bromide are insoluble, so the appearance of a precipitate is a positive test for the presence of an alkyl chloride or bromide.

a) Explain why these conditions favor the SN2 mechanism.

b) Which of these halides would give a precipitate more rapidly when reacted with NaI in acetone?

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