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

Question:

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 inacetone?

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Organic Chemistry

ISBN: 978-0534389512

2nd Edition

Authors: Joseph M. Hornback

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Question Posted: Jan 07, 2011 04:48 AM

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

Question:

acetone Na R-I + NACI (s) R-CI + -CI or CI Br i) CI ii) or CI Br Br iii) CH,CH,CI iv) or or

Step by Step Answer:

a A strong nucleophile iodide anion and an aprotic solvent acetone ...View the full answer

Organic Chemistry

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