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ChemistrySingle correct+4 / -1Question 63 of 75

The major product of which of the following reaction is not obtained by rearrangement reaction ?

A

Option A: benzene + 1-chloropropane with anhydrous AlCl₃ gives isopropylbenzene (cumene).

B

Option B: tert-butyl alcohol with H₃O⁺ gives 2-methylpropene.

C

Option C: n-hexane, CH₃(CH₂)₄CH₃, with anhydrous AlCl₃/HCl gives 2-methylpentane, CH₃CH(CH₃)(CH₂)₂CH₃.

D

Option D: neopentyl alcohol, (CH₃)₃C-CH₂OH, with H₃O⁺ gives 2-methylbut-2-ene.

Answer and worked solution

Official answer: B

Each reaction.

A: The n-propyl cation rearranges to isopropyl, giving cumene.
B: tert-Butyl alcohol gives the tert-butyl cation, which loses a proton to 2-methylpropene without rearrangement.
C: AlCl₃/HCl isomerises n-hexane to 2-methylpentane (a rearrangement).
D: The neopentyl cation undergoes a methyl shift, giving 2-methylbut-2-ene.

(B)

Topics:Reactive intermediates Aromatic hydrocarbons and electrophilic substitution Alcohols

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