Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser
Chapter 20 Homework Answers
Brown & Foote, pages 823 - 829:
Problems 20.7 - 24 , 27 - 31 , 35 , 39
Answers to all problems from the text can be found in the Study Guide.
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.
