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Organic Chemistry III

Nitration, halogenation, Friedel-Crafts and phenol

  • 3 things to know
  • Papers 2 and 3

Overview

The mechanisms of halogenation, nitration and Friedel-Crafts alkylation and acylation of benzene, including how each electrophile forms and each catalyst is regenerated, and why phenol decolourises bromine water to give 2,4,6-tribromophenol without a catalyst.

What you need to know

Answer each one before you reveal it.

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Key term

What is the formula of the electrophile in the nitration of benzene, and how is it generated?

Key term

What is the formula of the electrophile generated in Friedel-Crafts acylation?

Key term

What intermediate is formed when the positive halogen ion attacks benzene during halogenation?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What intermediate is formed when the positive halogen ion attacks benzene during halogenation?

    Model answer

    A carbocation intermediate.

  2. 2

    How is aromaticity restored in the final step of benzene halogenation?

    Model answer

    A hydrogen ion is lost and bonds with the halogen carrier complex, regenerating the catalyst and releasing HX.

  3. 3

    What is the formula of the electrophile in the nitration of benzene, and how is it generated?

    Model answer

    The nitronium ion (NO₂⁺), generated when concentrated sulfuric acid protonates nitric acid, which then loses water.

  4. 4

    What intermediate forms when the nitronium ion attacks benzene?

    Model answer

    A carbocation intermediate.

  5. 5

    How is the sulfuric acid catalyst regenerated in the nitration mechanism?

    Model answer

    A hydrogen ion is lost from the carbocation intermediate and regenerates the sulfuric acid.

  6. 6

    In Friedel-Crafts alkylation, how is the carbocation electrophile generated?

    Model answer

    Aluminium chloride accepts a lone pair from the halogen of the halogenoalkane, generating a carbocation.

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