Bruice 6th Ed. (2010)
CH 15: Aromaticity • Reactions of Benzene

Solutions can be seen at mendelset.com/chapters/1114


  1. 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.

  2. 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.)

  3. 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.

  4. Problem # 587

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

  5. 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?

  6. 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.

  7. Problem # 596

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

  8. Problem # 678

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

  9. Problem # 722

    Show how to prepare vinyl benzene from benzene.