Question:

(R)-2-Iodobutane is treated with $NaI$ in acetone and allowed to stand for a long time. The product eventually formed is

Updated On: Jul 28, 2022
  • (R)-2-iodobutane
  • (S)-2-iodobutane
  • ($\pm$)-2-iodobutane
  • ($\pm$)-1, 2-diiodobutane.
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The Correct Option is C

Solution and Explanation

I is a good nucleophile as well as a good leaving group. Therefore, if (R)-2-iodobutane is treated with NaI, repeated S2 reactions occur. As a result, eventually a racemic mixture of $\left(\pm\right)$-2-iodobutane is obtained.
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Concepts Used:

Introduction to Organic Chemistry

Organic chemistry is the branch of chemistry that involves the scientific study of organic compounds. Organic chemistry primarily deals with the structure and chemical composition of organic compounds, the physical and chemical properties of organic compounds, and the chemical reactions undergone by these compounds.

Reaction Intermediates in Organic Chemistry:

Intermediates can be understood as the first product of a consecutive reaction. For example, in a chemical reaction, if A→B and B→C, then, B can be said to be the intermediate for reaction A→C. The reactions in organic chemistry occur via the formation of these intermediates.

Reagents in Organic Chemistry:

Reagents are the chemicals that we add to bring about a specific change to an organic molecule. Any general reaction in organic chemistry can be written as:

Substrate + Reagent → Product

Where the substrate is an organic molecule to which we add the reagent. Based on the ability to either donate or abstract electrons, the reagents can be classified as:

  • Electrophiles
  • Nucleophiles