What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?
Practice Questions
1 question
Q1
What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?
Retention of configuration
Inversion of configuration
Racemization
No reaction
The reaction proceeds via an SN2 mechanism, leading to inversion of configuration at the chiral center.
Questions & Step-by-step Solutions
1 item
Q
Q: What is the stereochemical outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?
Solution: The reaction proceeds via an SN2 mechanism, leading to inversion of configuration at the chiral center.
Steps: 5
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.
