medium · MCAT chem-phys
Consider the S_N2 reaction between (S)-2-bromobutane and sodium hydroxide in a polar aprotic solvent.
What will be the stereochemical outcome and the primary reason for that outcome?
- A racemic mixture of 2-butanol due to the formation of a planar carbocation intermediate
- Formation of (R)-2-butanol due to backside attack by the nucleophile
- Retention of configuration, yielding (S)-2-butanol
- No reaction will occur because secondary substrates cannot undergo S_N2 substitution.
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