Chem 336 - Spring 2000
Organic Chemistry III
Dr. Carl C. Wamser

Chapter 20 Homework Answers

Brown & Foote, pages 823 - 829:
Problems 20.7 - 24 , 27 - 31 , 35 , 39

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.