Saturated sodium iodide in acetone test for primary and secondary alkyl halides Sodium iodide is more soluble in acetone than sodium chloride or sodium bromide. Acetone is a polar aprotic solvent which is suitable for SN2 reactions. Iodide is an excellent nucleophile. Bromide and chloride are good leaving groups. Primary alkyl halides react quickly by the SN2 mechanism. Write the mechanism and predict the product for the reaction between a primary alkyl chloride and sodium iodide (the compound should contain 15 carbon atoms). Explain why quick formation of a white precipitate upon treating a compound with saturated sodium iodide in acetone serves as evidence that the compound is a primary alkyl chloride or primary alkyl bromide.

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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  1. Saturated sodium iodide in acetone test for primary and secondary alkyl halides

Sodium iodide is more soluble in acetone than sodium chloride or sodium bromide. Acetone is a polar aprotic solvent which is suitable for SN2 reactions. Iodide is an excellent nucleophile. Bromide and chloride are good leaving groups. Primary alkyl halides react quickly by the SN2 mechanism. Write the mechanism and predict the product for the reaction between a primary alkyl chloride and sodium iodide (the compound should contain 15 carbon atoms). Explain why quick formation of a white precipitate upon treating a compound with saturated sodium iodide in acetone serves as evidence that the compound is a primary alkyl chloride or primary alkyl bromide.

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