Textbook: Vollhardt 6th Ed. (2010)

Chapter 15: Benzene and Aromaticity: Electrophilic Aromatic Substitution

Practice Problems (No matching mendel sets were found.)

Individual Problems

Problem # 587

Use curved arrows to draw a mechanism for the generic electrophilic aromatic substitution (EAS) reaction below.

Problem # 596

Indicate the eletrophile formed by each set of reagents/conditions below.

Problem # 678

Draw the structure of the major organic product from each reaction sequence.

Problem # 582

Rationalize the follwing pKa values. Explain your answer in terms of the stabilites of the conjugates bases of each acid.

Note: the lower the pKa, the stronger the acid.

Problem # 583

Pyrrole is an example of a heteroaromatic compound: it contains a heteroatom (atom that is not carbon or hydrogen, such as N, O, S, etc.), and is aromatic.

Because pyrrole is aromatic, we should be able to draw many resonance forms- usually as many resonance forms as sides (in this case, five sides, so five resonane forms).

Draw all resonance forms for pyrrole. (I've started you off.)

Problem # 584

Imidazole (shown below) has two nitrogen atoms, N-1 and N-3. Which nitrogen is more basic?

To answer this problem, draw the product after each nitrogen protonates, and compare their stabilities. Explain your reasoning.

Problem # 595

Phenol can be prepared from benzene and hydrogen peroxide in the presence of a really strong acid. Propose a mechanism for this reaction.

Problem # 722

Show how to prepare vinyl benzene from benzene.

Problem # 594

A chemist tried to prepare compound A from benzene via Friedel-Crafts alkylation and instead produced compound B.

Why did this happen? How could the chemist prepare compound A?