Mark Bishop

Analytical Chemistry and

Signal Acquisition/Analysis



Polynuclear aromatic hydrocarbons

Naphthalene

Reactions

Oxidation

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Reduction

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Aromatization (catalytic dehydrogenation)

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Proton scavengers also work.

Electrophilic Substitution

Activating group directs substitution into the same ring. Deactivating directs substitution into other ring.

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Synthesis of Naphthols

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Synthesis of naphthalene derivatives by ring closure. Haworth synthesis

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Notes:

  • 1) A substituted benzene may be used and a b  substituted naphthalene obtained
  • 2) The intermediate cyclic ketone can be treated with a Grignard reagent introducing a alkyl or aryl group into the a position.
  • 3) The keto acid in the form of its ester can be treated with a Grignard reagent introducing a alkyl or aryl group into the a position.

Phenanthrene and anthracene

Reactions

Oxidation and reduction

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Electrophilic attack

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ID may be exposed