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Problems and exercisesAromatic Compounds

1. Aromatic or not?

Which of these compounds are aromatic? a) cyclohexa-1,3-diene; b) toluene; c) pyridine; d) cyclooctatetraene; e) naphthalene; f) cyclohexene.

2. Addition versus substitution

Cyclohexene instantly decolorizes a bromine solution, but benzene does not react with bromine unless FeBr3 is added, and then it gives bromobenzene instead of a dibromide. Explain the difference.

3. Reagents and products

Write the main product of the reaction of benzene with: a) HNO3/H2SO4; b) Cl2/FeCl3; c) SO3/H2SO4; d) CH3COCl/AlCl3; e) (CH3)3CCl/AlCl3.

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