A Levels Chemistry (9701)•9701/11/O/N/21

Explanation
SN1 Mechanism for Tertiary Alkyl Halide
Steps:
- Identify substrate: 2-bromo-2-methylpropane is (CH3)3CBr, a tertiary alkyl halide.
- Determine reaction type: Aqueous NaOH favors SN1 for tertiary halides due to carbocation stability and polar protic solvent.
- Recall SN1 steps: Rate-determining first step is unimolecular loss of leaving group (Br-) to form planar carbocation.
- Match to diagram: First step shows heterolytic C-Br cleavage, producing (CH3)3C+ and Br-.
Why B is correct:
- B illustrates carbocation formation via ionization, aligning with SN1 rate law (rate = k[RX]) where leaving group departs without nucleophile involvement.
Why the others are wrong:
- A: Depicts nucleophilic attack on carbon, characteristic of SN2 bimolecular mechanism unsuitable for sterically hindered tertiary carbon.
- C: Shows simultaneous bond breaking and forming, resembling concerted SN2 or E2, not stepwise SN1.
- D: Illustrates Br- abstraction by base, suggesting E2 elimination rather than substitution.
Final answer: B
Topic: Halogen compounds
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