Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2004

Chapter 11 Quiz

Aromaticity

1. (5 points) Write the five major resonance forms for the aromatic hydrocarbon phenanthrene, shown below without its seven pi bonds.

2. (1 point) One double bond in phenanthrene behaves much like a normal alkene (adds Br2, for example). Predict which double bond that would be (circle it in one of your resonance forms).

see above

3. (4 points) Write a complete mechanism for the E1 dehydration of 1-phenylethanol using H2SO4. Include all the resonance forms of the benzylic cation intermediate.