JEE Main · 2025 · Shift-IIeasyGOC-096

Which among the following halides will generate the most stable carbocation in Nucleophilic substitution reaction?

General Organic Chemistry (GOC) · Class 11 · JEE Main Previous Year Question

Question

Which among the following halides will generate the most stable carbocation in Nucleophilic substitution reaction?

Options
  1. a

    Allyl bromide

  2. b

    Bromobenzene

  3. c

    Cyclohexyl bromide

  4. d

    Triphenylmethyl bromide

Correct Answerd

Triphenylmethyl bromide

Detailed Solution

Step 1: Carbocation Stability in SN1S_N1 Nucleophilic substitution (especially SN1S_N1) involves a carbocation intermediate.

  • (d) Triphenylmethyl bromide: Generates the trityl cation, which is stabilized by three phenyl rings via resonance. It is extremely stable.
  • (a) Allyl: stabilized by one double bond.
  • (b) Benzyl (if it were benzyl, but it's bromobenzene which gives an unstable aryl cation).
  • (c) Cyclohexyl: secondary alkyl (relatively unstable).

Answer: (d) Triphenylmethyl bromide\boxed{\text{Answer: (d) Triphenylmethyl bromide}}

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