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MCQMediumJEE 2026Electrophilic Substitution in Benzene

JEE Chemistry 2026 Question with Solution

Consider the following compounds. Arrange these compounds in a n increasing order of reactivity with nitrating mixture. The correct order is :

Three benzene derivatives labeled a, b, and c are shown: chlorobenzene as a, nitrobenzene as b, and anisole with OCH3 group as c.
  • A

    c<b<ac < b < a

  • B

    b<c<ab < c < a

  • C

    b<a<cb < a < c

  • D

    c<a<bc < a < b

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: Three substituted benzenes a, b, and c are to be arranged in increasing order of reactivity with nitrating mixture.

Find: The correct increasing order of reactivity.

From the figure, a = chlorobenzene, b = nitrobenzene, and c = anisole.

The nitration of benzene derivatives is an electrophilic aromatic substitution reaction. The reactivity depends on whether the substituent activates or deactivates the ring toward electrophilic attack.

  • −NO2-NO_2 is a strong electron-withdrawing group, so nitrobenzene is strongly deactivated.
  • −Cl-Cl is deactivating overall due to its −I-I effect, so chlorobenzene is less reactive than benzene.
  • −OCH3-OCH_3 donates electron density by resonance, so anisole is strongly activated.

Therefore, the increasing order of reactivity with nitrating mixture is

b<a<cb < a < c

The solution states option A, but its written explanation discusses acidity of phenol derivatives, which is unrelated to this question. Based on the compounds shown, the defensible correct option is C.

Common mistakes

  • Treating chlorobenzene as more reactive than anisole because halogens can donate by resonance is incorrect. The overall deactivating −I-I effect of −Cl-Cl reduces ring reactivity, whereas −OCH3-OCH_3 strongly activates the ring by resonance donation.

  • Assuming nitrobenzene can react faster because it already contains a nitro group is incorrect. The −NO2-NO_2 group is strongly electron-withdrawing and makes the ring least reactive toward further nitration.

  • Relying only on the solution text is a mistake here because that explanation is for acidity of phenol derivatives, not nitration reactivity of the shown compounds. Use the actual structures in the image and electrophilic substitution principles instead.

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