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Aromatic Compounds

  • 6 subtopics
  • 11 things to know
  • Components 02 and 03

What Aromatic Compounds covers

Benzene's delocalised structure and the evidence for it, electrophilic substitution and the directing effects of substituents, and phenol, which reacts far more readily than benzene and shows why.

Where it is assessed

Components 02 and 03

Synthesis and Analytical Techniques, then the unified paper.

Check the OCR specification ↗

The 6 subtopics

Each one has its own page.

What you need to know

Answer each one before you reveal it.

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Process

What system do the overlapping p-orbitals form in benzene, and how do its enthalpy of hydrogenation and its C–C bond lengths support the delocalised model?

Numbers

What is required for the halogenation of benzene, which species is the electrophile in nitration, and how does phenol react with sodium hydroxide?

Key term

What forms when phenol reacts with bromine water, is a catalyst needed, and what forms when phenol reacts with dilute nitric acid?

Key term

Give two examples of electron-donating groups and state which positions they direct substitution to.

Process

What is the characteristic reaction mechanism of aromatic compounds?

Key term

If a nitro group (–NO₂) is attached to a benzene ring at position 1, at which positions would a second substituent most likely be introduced?

Key term

What are 3-directing groups and which positions do they direct substitution to?

Key term

How can phenol be told apart from a carboxylic acid, does phenol need a halogen carrier to react with bromine water, and what temperature is needed?

Numbers

What concentration of nitric acid nitrates phenol, is a concentrated sulfuric acid catalyst needed, and which type of orbital holds the oxygen lone pair that activates the ring?

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?

Take Aromatic Compounds further

The same content, four other ways.

Commonly confused

Pairs that lose marks when they are blurred together.

  • Aliphatic compound vs Aromatic compound

    Aliphatic compound: a carbon compound without an aromatic ring. Aromatic compound: a compound containing a stable delocalised ring system.

  • Electrophilic addition vs Electrophilic substitution

    Electrophilic addition: an electron-pair acceptor adding across a multiple bond. Electrophilic substitution: an electron-pair acceptor replacing a hydrogen atom on an aromatic ring.

Questions from this topic

Each one with the model answer underneath.

  1. 1

    What structure did Kekulé propose for benzene?

    Model answer

    A hexagonal ring with alternating single and double carbon-carbon bonds.

  2. 2

    In the delocalised model of benzene, how do the p-orbitals on each carbon atom interact?

    Model answer

    The p-orbitals from each carbon atom overlap above and below the plane of the ring.

  3. 3

    What type of system is formed when the p-orbitals in benzene overlap, and how is the electron density distributed?

    Model answer

    A delocalised π-system is formed, with electron density distributed equally around the ring.

  4. 4

    What are the two ways benzene can be represented in structural diagrams?

    Model answer

    As a hexagon with a circle inside, or as a hexagon with alternating double bonds.

  5. 5

    What is the carbon-carbon bond length in benzene, and how does this provide evidence for delocalisation?

    Model answer

    All C-C bond lengths are equal at 0.139 nm, which is intermediate between single bond length (0.154 nm) and double bond length (0.134 nm).

  6. 6

    How does the enthalpy change of hydrogenation of benzene provide evidence for delocalisation?

    Model answer

    The enthalpy change of hydrogenation is less exothermic than expected for a structure with three isolated double bonds.

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Foundations in Chemistry
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Enthalpy Changes

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AThe first step is Cl• + O₃ → ClO• + O₂.
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Aromatic Compounds revision questions

What does Aromatic Compounds cover in OCR A-Level Chemistry?
6 subtopics: the delocalised model of benzene and the evidence for it, nitration, halogenation and friedel-crafts reactions of benzene, the reactions of phenol, and directing effects, electrophilic substitution and directing effects, phenol: acidity, bromination and nitration and why phenol is more reactive than benzene, and planning a synthesis. Each one has its own page with questions and model answers.
How is Aromatic Compounds organised?
By the OCR H432 specification, subtopic by subtopic, so it matches the order you are taught it in.

Every question in Aromatic Compounds, on a schedule.

Attempt a question from memory, write the correct version, then attempt it again. Levo records the jump between your first attempt and your last, and brings each question back on the day you are due to forget it.

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