JEE Main · 2025 · Shift-IhardGOC-106

Which one of the carbocations from the following is most stable?

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

Question

Which one of the carbocations from the following is most stable?

Options
  1. a

    CH2+\overset{+}{\text{CH}_2}–CH=CH–CH₂–O–CH₃

  2. b

    CH2+\overset{+}{\text{CH}_2}–CH=CH–O–CH₃

  3. c

    CH2+\overset{+}{\text{CH}_2}–CH=CH–O–C(=O)–CH₃

  4. d

    CH2+\overset{+}{\text{CH}_2}–CH=CH–F

Correct Answerb

CH2+\overset{+}{\text{CH}_2}–CH=CH–O–CH₃

Detailed Solution

Carbocation stability — key factors: Resonance > Hyperconjugation > Inductive effects.

Option (b): CH2+–CH=CH–OCH3\overset{+}{\text{CH}_2}\text{–CH=CH–OCH}_3

This is an allylic carbocation where the oxygen of –OCH₃ is directly conjugated with the double bond:

CH2+–CH=CH–O–CH3CH2=CH–CH=O+–CH3\overset{+}{\text{CH}_2}\text{–CH=CH–O–CH}_3 \longleftrightarrow \text{CH}_2\text{=CH–CH=}\overset{+}{\text{O}}\text{–CH}_3

The oxygen lone pair delocalises into the carbocation through the π system → oxocarbenium resonance → maximum stabilisation.

Comparison:

  • (a): –OCH₃ is separated by –CH₂– (no direct conjugation with +)
  • (c): Ester oxygen is less electron-donating (carbonyl withdraws electrons)
  • (d): F is electronegative; –I effect destabilises carbocation

Most stable: (b)

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