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O Levels Chemistry (5070)•5070/12/O/N/23
Question 35 from 5070/12/O/N/23

Explanation

Structural isomers from hydrogen substitution in n-butane

Steps:

  • Represent butane as CH₃-CH₂-CH₂-CH₃, with carbons labeled 1-2-3-4.
  • Identify equivalent positions: C1 and C4 (terminal methyl, primary H); C2 and C3 (methylene, secondary H).
  • Substitution at C1 (or C4) forms 1-chlorobutane: CH₃-CH₂-CH₂-CH₂Cl.
  • Substitution at C2 (or C3) forms 2-chlorobutane: CH₃-CH₂-CHCl-CH₃.

Why B is correct:

  • n-Butane has two sets of equivalent hydrogens (primary and secondary), producing two distinct carbon skeletons for chlorobutane per structural isomer definition.

Why the others are wrong:

  • A: Ignores positional differences between primary and secondary carbons.
  • C: Overcounts by possibly including stereoisomers, which are not structural.
  • D: Assumes all four carbons are unique, but C1≡C4 and C2≡C3.

Final answer: B

Topic: Alkanes

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