McMurry 8th Ed. (2011)
CH 15: Benzene and Aromaticity

Solutions can be seen at mendelset.com/chapters/798


  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.