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What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with

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Question: What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with sodium iodide?

Options:

  1. (R)-2-iodobutane
  2. (S)-2-iodobutane
  3. (R)-2-bromobutane
  4. (S)-2-bromobutane

Correct Answer: (S)-2-iodobutane

Solution:

The SN2 mechanism inverts the configuration at the chiral center, resulting in (S)-2-iodobutane.

What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with

Practice Questions

Q1
What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with sodium iodide?
  1. (R)-2-iodobutane
  2. (S)-2-iodobutane
  3. (R)-2-bromobutane
  4. (S)-2-bromobutane

Questions & Step-by-Step Solutions

What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with sodium iodide?
  • Step 1: Identify the starting compound, which is (R)-2-bromobutane. This compound has a specific 3D arrangement of atoms around the chiral center.
  • Step 2: Understand that the SN2 reaction involves a nucleophile (in this case, sodium iodide) attacking the carbon atom that is bonded to the bromine atom.
  • Step 3: Recognize that during the SN2 reaction, the bromine atom leaves, and the iodide ion from sodium iodide takes its place.
  • Step 4: Note that the SN2 mechanism causes the configuration at the chiral center to invert. This means that if the starting compound was (R), the product will be (S).
  • Step 5: Conclude that the final product of the reaction is (S)-2-iodobutane.
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