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Organic Chemistry III

The structure of benzene and the evidence for it

  • 3 things to know
  • Papers 2 and 3

Overview

Recall questions on the Kekulé structure and the delocalised model, and on the bond lengths, hydrogenation enthalpies and lack of reactivity that decide between them.

What you need to know

Answer each one before you reveal it.

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Evaluation

What evidence rules out the Kekule structure for benzene?

Key term

Why does benzene burn with a smoky flame?

Key term

How does the Kekulé model represent the structure of benzene?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    How does the Kekulé model represent the structure of benzene?

    Model answer

    As a hexagonal ring with alternating single and double carbon-carbon bonds.

  2. 2

    In the delocalised model of benzene, what type of orbital does each carbon atom contribute to the π-system?

    Model answer

    Each carbon atom has one unhybridised p-orbital perpendicular to the ring plane.

  3. 3

    How do the p-orbitals in benzene interact to form the delocalised system?

    Model answer

    Adjacent p-orbitals overlap sideways.

  4. 4

    Describe the distribution of electrons in the delocalised model of benzene.

    Model answer

    Electrons are shared across all six carbon atoms, forming two ring-shaped electron clouds above and below the plane of the ring.

  5. 5

    What enthalpy of hydrogenation would be predicted for cyclohexatriene based on the Kekulé structure?

    Model answer

    Approximately three times the enthalpy of hydrogenation of cyclohexene.

  6. 6

    How does the actual enthalpy of hydrogenation of benzene compare to the predicted value for cyclohexatriene?

    Model answer

    Benzene releases significantly less energy than the predicted value for cyclohexatriene.

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