Aromatic Compounds and Electrophilic Substitution - Higher Difficulty Problems

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This section is dedicated to challenging, multi-concept, and mechanism-intensive problems involving aromatic compounds and electrophilic substitution reactions. It is designed for advanced Class 11–12 students, competitive exam aspirants, and undergraduate learners who aim to develop strong mechanistic insight and problem-solving precision in aromatic chemistry.

In this section, you will work on:

  • Advanced problems on aromaticity and resonance stability

  • Mechanism-based questions on electrophilic aromatic substitution (EAS)

  • Orientation and directive influence in substituted benzene systems

  • Multi-substitution and regioselectivity prediction problems

  • Comparative reactivity and activation–deactivation analysis

  • Problems involving σ-complex (arenium ion) stability

  • Integration of inductive, resonance, and hyperconjugative effects

  • High-trap questions inspired by competitive and UG-level exams

The content is structured to enhance deep conceptual understanding, improve logical reasoning, and prepare students to tackle complex and time-pressured questions in school finals, JEE-type exams, and undergraduate assessments.

Sharpen your mastery of aromatic compounds by solving higher-difficulty problems that test true understanding beyond rote learning.

Q. In the nitration of benzene, what is the role of sulfuric acid?
  • A. Nucleophile
  • B. Electrophile
  • C. Catalyst
  • D. Solvent
Q. In the presence of a strong electrophile, which position on a disubstituted benzene ring will a third substituent most likely attach?
  • A. Ortho
  • B. Meta
  • C. Para
  • D. Random
Q. What is the effect of a strong electron-donating group on the rate of electrophilic aromatic substitution?
  • A. Decreases the rate
  • B. Increases the rate
  • C. No effect
  • D. Reverses the reaction
Q. What is the expected product when anisole is treated with chlorosulfonic acid?
  • A. Anisole sulfonic acid
  • B. p-Anisole sulfonic acid
  • C. o-Anisole sulfonic acid
  • D. No reaction
Q. What is the IUPAC name of the compound formed when phenol undergoes bromination?
  • A. Bromophenol
  • B. 2-Bromophenol
  • C. 4-Bromophenol
  • D. Bromobenzene
Q. What is the major product of the electrophilic substitution of toluene with bromine in the presence of FeBr3?
  • A. Bromotoluene
  • B. Bromobenzene
  • C. Benzyl bromide
  • D. No reaction
Q. Which mechanism is primarily involved in the electrophilic substitution of aromatic compounds?
  • A. SN1
  • B. SN2
  • C. E1
  • D. E2
Q. Which of the following substituents is a deactivating group in electrophilic aromatic substitution?
  • A. Methyl
  • B. Hydroxyl
  • C. Nitro
  • D. Ethyl
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