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A Levels Chemistry (9701)•9701/13/O/N/20
Question 21 from 9701/13/O/N/20

Explanation

Alkene structure, isomerism, and HBr addition rules

Steps:

  • Draw 2-methylbut-1-ene: CH2=C(CH3)CH2CH3, with terminal double bond.
  • Check geometrical isomers: C1 has two H atoms (identical substituents), so no cis-trans isomerism possible.
  • Predict HBr addition: Markovnikov rule directs H to C1 (more hydrogens) and Br to C2, yielding CH3CBr(CH3)CH2CH3 (2-bromo-2-methylbutane).
  • Compare to Student 2's product: 1-bromo-2-methylbutane is BrCH2CH(CH3)CH2CH3 (anti-Markovnikov, not major).

Why D is correct:

  • Both statements fail: no geometrical isomers due to identical substituents on C1 (definition of cis-trans isomerism), and major HBr product is 2-bromo-2-methylbutane per Markovnikov's rule (H adds to carbon with more H's).

Why the others are wrong:

  • A: Both students incorrect, as explained.
  • B: Student 1 wrong; no geometrical isomers.
  • C: Student 2 wrong; product is not 1-bromo-2-methylbutane.

Final answer: D

Topic: Hydrocarbons

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