What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

Question

Quizplus · Accepted Answer

Treatment of (R)-pentan-2-ol with TsCl (tosyl chloride) followed by NaI (sodium iodide) leads to substitution of the tosyl group (Ts) with iodine. The tosyl group is a good leaving group and is replaced by iodine due to the higher nucleophilicity of iodine compared to tosylate ion. The resulting product is (S)-2-iodopentane, as the stereochemistry is inverted due to the SN2 mechanism of substitution. Therefore, the correct answer is D.

What Compound Is Produced When (R)-Pentan-2-Ol Is Treated with TsCl