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

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Question: What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?

Options:

Correct Answer: Inversion of configuration

Solution:

The reaction proceeds via an SN2 mechanism, leading to inversion of configuration at the chiral center.

What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?

What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?

Step 1: Identify the starting material, which is (R)-2-bromobutane. This molecule has a chiral center at the second carbon.
Step 2: Recognize that NaOH is a strong nucleophile and will attack the carbon that is bonded to the bromine atom.
Step 3: Understand that the reaction takes place in a polar aprotic solvent, which supports the SN2 mechanism.
Step 4: In an SN2 reaction, the nucleophile attacks the carbon from the opposite side of the leaving group (bromine), leading to a backside attack.
Step 5: As a result of the backside attack, the configuration at the chiral center is inverted. If the starting material is (R)-2-bromobutane, the product will be (S)-2-butanol.

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