Medical Chemistry Lecture 9: Aromatic Compounds

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What is unique about the chemical reactivity of benzene?

It is resistant to addition reactions and reacts under more vigorous conditions.

How are monosubstituted benzene compounds named?

By placing the name of the group as a prefix to the benzene.

Why do disubstituted benzenes require specific naming?

Because the location of the groups on the ring is important.

What type of reactions do toluene, nitrobenzene, and chlorobenzene undergo?

Substitution reactions.

What is the result of substitution reactions in toluene, nitrobenzene, and chlorobenzene?

Isomers can be formed depending on which hydrogen is replaced.

What is a characteristic of Friedel-Crafts Acylation?

It involves the substitution of an acyl group.

Why do some disubstituted benzenes have specific names?

Because they have been given specific names.

What is the difference between Friedel-Crafts Alkylation and Friedel-Crafts Acylation?

One involves the substitution of an alkyl group, the other involves the substitution of an acyl group.

Study Notes

Aromatic Compounds

  • Benzene has a high degree of unsaturation but is unreactive, doesn't undergo usual addition reactions of alkenes and alkynes.
  • Benzene reacts under more vigorous conditions (heat or catalysts) to form products of substitution.
  • The unique chemical reactivity of benzene is due to its structure.

Naming Aromatic Compounds

  • When one group is attached to benzene, the compound is named by placing the name of the group as prefix to the benzene.
  • If two groups are attached to the benzene ring, the name must indicate what groups are present and their location.

Isomers of Disubstituted Benzenes

  • There are three possible isomers of a disubstituted benzene, which can be differentiated in two ways.
  • Some disubstituted benzenes have been given names that don't indicate the kind of groups attached to the ring.

Substitution Reactions of Aromatic Compounds

  • Bromination is a type of substitution reaction of aromatic compounds.
  • Chlorination is a type of substitution reaction of aromatic compounds.
  • Nitration is a type of substitution reaction of aromatic compounds.
  • Sulfonation is a type of substitution reaction of aromatic compounds.
  • Friedel-Crafts Alkylation is a type of substitution reaction of aromatic compounds.
  • Friedel-Crafts Acylation is a type of substitution reaction of aromatic compounds.

Substitution Reactions of Substituted Benzenes

  • Toluene, nitrobenzene, chlorobenzene, and many other aromatic compounds undergo substitution reactions.
  • These compounds differ from benzene in that they already have a substituent on the benzene ring.
  • Isomers can be formed depending on which hydrogen is replaced during substitution reactions.

Learn about the unique properties of benzene and its reactivity in aromatic compounds, covering the basics of medical chemistry.

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