Show how each of the following compounds can be prepared from methyl phenyl ketone:
c.

Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient. For example, furan reacts with bromine to give 2-bromofuran.

a. Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms of each sigma complex, and compare their stabilities.

Styrene (vinylbenzene) undergoes electrophilic aromatic substitution much faster than benzene, and the products are found to be primarily ortho- and para-substituted styrenes. Use resonance forms of the intermediates to explain these results.

What products would you expect from the following coupling reactions?

(b)

What products would you expect from the following coupling reactions?

(a)

Indicate how the following compounds can be synthesized from cyclohexanone and any other necessary reagents:

d.

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

b. Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than the 3-position.

a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.

We have considered nucleophilic aromatic substitution of pyridine at the 2-position and 3-position but not at the 4-position. Complete the three possible cases by showing the mechanism for the reaction of methoxide ion with 4-chloropyridine. Show how the intermediate is stabilized by delocalization of the charge onto the nitrogen atom.