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A Levels Chemistry (9701)•9701/12/O/N/23
Question 30 from 9701/12/O/N/23

Explanation

Conjugated diene undergoes 1,4-addition with HBr

Steps:

  • Compound X is a conjugated diene, allowing electrophilic addition of two HBr molecules.
  • First HBr adds via protonation at one double bond, forming a resonance-stabilized allylic carbocation.
  • Bromide attacks the carbocation at the 1,4-position (major) or 1,2-position (minor).
  • Second HBr adds to the remaining double bond in the 1,4-product, yielding the saturated dibromide.

Why A is correct:

  • A shows the 1,4-dibromide product, following Markovnikov's rule for conjugated systems where the major pathway stabilizes the allylic intermediate.

Why the others are wrong:

  • B: Represents 1,2-addition product after first HBr, ignoring second addition.
  • C: Shows anti-Markovnikov orientation, violating regioselectivity in HBr addition.
  • D: Depicts a non-conjugated or incorrect skeletal structure, not matching diene reactivity.

Final answer: A

Topic: Hydrocarbons

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