Question: Iodoalkanes are readily prepared from the corresponding chloro compounds by SN2 reaction with sodium iodide in acetone. This particular procedure is especially useful because the

Iodoalkanes are readily prepared from the corresponding chloro compounds by SN2 reaction with sodium iodide in acetone. This particular procedure is especially useful because the inorganic by-product, sodium chloride, is insoluble in acetone; its precipitation drives the equilibrium in the desired direction. Thus, it is not necessary to use excess NaI, and the process goes to completion in a very short time. Because of its great convenience, this method is named after its developer (the Finkelstein reaction). In an attempt to synthesize optically pure (R)-2-iodoheptane, a student prepared a solution of (S)-2-chloroheptane in acetone. In order to ensure success, he added excess sodium iodide and allowed the mixture to stir over the weekend. His yield of 2-iodoheptane was high, but, to his dismay, he found that his product was racemic. Explain.

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