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Asked by shahed saflow on Sep 28, 2024

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

A) sodium (R) -pent-3-oxide
B) sodium (S) -pent-2-oxide
C) (R) -2-iodopentane
D) (S) -2-iodopentane
E) none of the above

TsCl

P-toluenesulfonyl chloride, an organic compound used as a reagent in organic synthesis to introduce tosyl groups.

(R)-Pentan-2-Ol

An optically active form of pentanol where the hydroxyl group is attached to the second carbon atom in the pentane chain.

NaI

Sodium iodide, a salt commonly used in organic chemistry as a source of iodide ions in substitution reactions.

  • Comprehend the function of stereochemistry within organic chemical reactions.
  • Acquire knowledge about the mechanics behind nucleophilic substitution reactions.
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Verified Answer

JG
Jerardo Gomezabout 16 hours ago
Final Answer :
D
Explanation :
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.

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