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Colour by Design

Halogenation and nitration of benzene and the electrophiles involved

  • 1 thing to know
  • Components 01, 02 and 03

Overview

Recall questions on the reagents and conditions for each, the halogen carrier, and generating the nitronium ion.

What you need to know

Answer each one before you reveal it.

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Key term

Name the organic product and a suitable catalyst for the chlorination of benzene.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Which of Br⁺, Cl⁻ and H₂O can act as an electrophile, and why?

    Model answer

    Only Br⁺; it is positively charged and can accept a pair of electrons, whereas Cl⁻ and H₂O each have lone pairs to donate and so behave as nucleophiles.

  2. 2

    Why is benzene attacked by electrophiles?

    Model answer

    Its delocalised electron system forms a region of high electron density above and below the ring.

  3. 3

    Why is the overall outcome substitution rather than addition?

    Model answer

    The positively charged intermediate loses a hydrogen ion, which restores the stable delocalised ring instead of adding a second group.

  4. 4

    State the reagents and conditions for the bromination of benzene.

    Model answer

    Bromine with a halogen carrier catalyst such as iron(III) bromide, aluminium bromide or iron filings, at room temperature.

  5. 5

    Name the products of the bromination of benzene.

    Model answer

    Bromobenzene and hydrogen bromide.

  6. 6

    What is the role of the halogen carrier?

    Model answer

    It polarises the bromine molecule, generating a strong electrophile that the delocalised ring is able to attack.

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A3 ⁴₂He → ¹²₆C.
B¹²₆C + ⁴₂He → ¹⁶₈O.
C¹⁶₈O + ⁴₂He → ²⁰₁₀Ne.

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