JEE Main 2025 · 22 January · evening · Single correct · +4 / −1

The most stable carbocation from the following is :

  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (c)

Solution

Chemistry ma’am · 3 steps

All four are benzyl cations, so ask one thing: which group pushes the most electrons into that CH₂⁺?

  1. Common base. Each option is a benzyl cation, already stabilised by resonance with the ring. The positive charge spreads to the ortho and para carbons, so a substituent at the para position can interact with the charge directly. A group at the meta position cannot.
    OptionSubstituentEffect on the positive chargeResult
    (a)OCH₃ at metaNo resonance link to the charge, so only the -I pull of O actsless stable than benzyl
    (b)CH₃ at para+I and hyperconjugation, a mild pushmore stable than benzyl
    (c)OCH₃ at para+M: the lone pair on O delocalises right onto the benzylic carbonmost stable
    (d)nonering resonance onlyreference
  2. Why para-OMe wins. In (c) one resonance form is CH₃-O+=C₆H₄=CH₂, where every atom has a full octet. That extra contributor makes the +M effect of OCH₃ far stronger than the hyperconjugation from CH₃.
  3. So. The stability order is (c) > (b) > (d) > (a), and the most stable carbocation is (c), the p-methoxybenzyl cation.

The idea to keep. For substituted benzyl cations, look at position before group: ortho or para lets +M act on the charge, meta leaves only the inductive effect. A strong +M donor at para beats any alkyl group.

Answer from the NTA final answer key. Solution by PrepWiser.

Study General Organic Chemistry (GOC)

Asked about 180 times in JEE Main since 2020. This question is from 2025.