Topic 12 - Arenes: benzene and phenol
 

Benzene and Substituted Benzene Compounds

  1. Describe and explain the structure of arenes in terms of the delocalisation of electrons.
  2. Explain the structure of the benzene molecule in terms of s and p bonds and the concept of delocalisation of electrons.
  3. Describe the relative inertness of benzene compared to alkenes in addition reactions.
  4. Describe the chemistry of arenes as exemplified by the following reactions of benzene:
    1. substitution reactions with bromine, including the contrast with the reaction of cyclohexene with bromine
    2. nitration
    3. alkylation by the Friedel-Crafts reaction
    4. addition reaction with hydrogen and chlorine
  5. Describe the mechanism of electrophilic substitution in arenes, using the mono-nitration of benzene as an example.
  6. Describe the effect of the delocalisation of electrons in arenes in electrophilic substitution reactions.
  7. Predict whether halogenation will occur in the side chain or the aromatic nucleus in arenes depending on reaction conditions.

Phenols

  1. Recall the chemistry of phenols, as exemplified by the following reactions:
    1. combustion
    2. with bases
    3. with sodium
    4. with sodium carbonate
    5. with FeCl3.
  2. Explain the relative solubility and acidities of water, phenol and ethanol.
  3. Describe ester formation with acid chlorides and acid anhydrides.
  4. Describe the reactivity of the ring system with bromine and with nitric acid.
  5. Interpret reactions of phenols in terms of electrophilic and nucleophilic attack.

Infra-red Spectroscopy

  1. Suggest structures for a compound from its infra-red spectrum.
  2. Examine the effect of hydrogen bonding on infra-red spectra.

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