MCQEasyJEE 2025SN1 & SN2 Reactions

JEE Chemistry 2025 Question with Solution

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

  • A
    A cyclohexene ring bearing a bromo substituent attached to one carbon adjacent to the double bond.
  • B
    A benzene ring connected to a side chain ending in bromine, representing a phenethyl or related aryl alkyl bromide structure.
  • C
    A cyclohexane ring with a bromo substituent attached directly to one ring carbon.
  • D
    A central carbon bonded to bromine and three phenyl groups, representing triphenylmethyl bromide.

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: Four halides are provided, and we must identify which one generates the most stable carbocation in a nucleophilic substitution reaction.

Find: The option that forms the carbocation with the greatest stability.

Carbocation stability depends mainly on delocalization and resonance stabilization.

From the solution text:

  • the carbocation generated from option (4) is the most stable,
  • because it is stabilized by resonance involving the phenyl rings,
  • whereas the carbocations from options (1), (2), and (3) have less stabilization.

Thus, the halide in option D forms the most stable carbocation.

Therefore, the correct option is D.

Resonance Stabilization View

Given: Stability of the intermediate carbocation determines which halide is favored for substitution through carbocation formation.

Find: Which structure gives the most stabilized carbocation after loss of Br\text{Br}^-.

A carbocation becomes especially stable when its positive charge can be delocalized by resonance.

Option D corresponds to a highly resonance-stabilized carbocation because the positively charged carbon is attached to phenyl groups, allowing extensive delocalization of charge into the aromatic rings.

The other options do not provide comparable resonance stabilization.

Therefore, the most stable carbocation is obtained from option D.

Common mistakes

  • Focusing only on the presence of a halogen and ignoring carbocation stabilization is incorrect. In nucleophilic substitution involving carbocation formation, compare the stability of the carbocation formed after departure of the halide.

  • Assuming that any cyclic or unsaturated structure is automatically more stable is wrong. The key factor here is resonance delocalization of positive charge, especially through phenyl rings.

  • Confusing inductive effects with resonance effects can lead to the wrong choice. In this question, resonance stabilization is the dominant reason option D is favored, not merely alkyl substitution.

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