Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter Term

Chapter 12 Homework Answers

1. Write a complete mechanism for the Markovnikov addition of HBr to styrene. Show all resonance forms for the intermediate.

2. Consider whether the following substituents would be activating or deactivating, and also predict whether they would be meta- or ortho,para-directing. Write the best Lewis structures for each substituent to justify your answers.

-CNO , -NCO , -OCN

3. Write a complete mechanism for the Friedel-Crafts reaction of anisole with acetyl chloride, including all resonance forms for the intermediate. Indicate the most stable resonance form.

4. Pentachlorophenol (PCP) has been used as a wood preservative, but has the problem of generating polycyclic compounds (commonly called dioxins) that are toxic. Write a mechanism for the reaction below.