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Aromatic Compounds

Why phenol is more reactive than benzene, and planning a synthesis

  • 2 things to know
  • Components 02 and 03

Overview

Recall questions on the oxygen lone pair donated into the ring, its effect on electron density, and using directing effects to sequence a multi-step synthesis.

What you need to know

Answer each one before you reveal it.

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Key term

What does the donated oxygen lone pair do to the ring, and are the OH and NH₂ groups electron-donating or withdrawing?

Key term

To which position does an electron-withdrawing group such as NO₂ direct incoming electrophiles?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What type of orbital contains the lone pair on the oxygen atom in phenol that is involved in activating the ring?

    Model answer

    A p-orbital on the oxygen atom contains the lone pair.

  2. 2

    How does the lone pair on oxygen in phenol interact with the benzene ring?

    Model answer

    The lone pair in the oxygen p-orbital overlaps with the delocalised π-system of the benzene ring.

  3. 3

    What effect does the donation of the oxygen lone pair have on the electron density in phenol's benzene ring?

    Model answer

    The electron density in the benzene ring increases.

  4. 4

    Why does phenol undergo electrophilic substitution more readily than benzene?

    Model answer

    The increased electron density in the ring (due to lone pair donation from oxygen) makes the ring more susceptible to electrophilic attack.

  5. 5

    Is the OH group electron-donating or electron-withdrawing?

    Model answer

    The OH group is electron-donating.

  6. 6

    Is the NH₂ group electron-donating or electron-withdrawing?

    Model answer

    The NH₂ group is electron-donating.

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Foundations in Chemistry
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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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