Which of the following compounds will give a pair of enantiomers upon nucleophilic substitution reaction with a hydroxideion?
Answer & explanation
Correct answer: option 1
The correct answer is Option (1) → 2-bromobutane
Analyze each compound
- 2-bromobutane
- Structure: CH₃–CHBr–CH₂–CH₃
- C-2 is attached to: CH₃, CH₂CH₃, H, Br → chiral
- SN2 reaction with OH⁻ → inversion → pair of enantiomers possible
Yes
- 2-bromo-2-methylbutane
- Structure: (CH₃)₂CBr–CH₂–CH₃
- C-2 attached to: 2 CH₃, CH₂CH₃, Br → not 4 different groups → not chiral
No
- 1-bromo-3-methylbutane
- Br on primary carbon (C-1) → only 3 different groups (H, CH₂, CH₂CH(CH₃)₂?)
- C-1 not chiral → No
- 1-bromobutane
- Primary carbon, not chiral → No