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Reaction Mechanism for Enantiomerically Pure (S)-2-Iodobutane

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Enantiomerically pure (S)-2-Iodobutane is reacted with sodium iodide in acetone. The measured optical rotation of samples taken from the reaction mixture changes from an initial maximum value of +16 degrees, to 0 degrees over time. If the reaction is performed with isotopically labeled iodine it is found that the rate of decrease of measured optical rotation is almost exactly twice that of the rate of incorporation of the isotopic label.

(a) Give a mechanism for reaction that is occurring here.
(b) Draw a reaction diagram for the process.
(c) Explain how the rate of the decrease of optical rotation would be changed if the reaction was performed in water as the solvent instead of acetone.
(d) Explain the relative rates of decrease of optical rotation and isotopic label

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Solution Summary

The expert examines the reaction mechanism for enantiomerically pure (S)-2-iodobutane. The reaction diagram for the process are determined.