Chem 335 - Winter 2000
Organic Chemistry II
Dr. Carl C. Wamser

Chapter 10 Homework Answers

Brown & Foote, pages 388 - 393:
Problems 10.7 - 19, 21, 22, 24 - 28

1. Give complete names for each of the following:

a)

(R),(E)-1-bromo-1-cyclopentylhex-4-en-2-yne

b)

(S),(E)-3-chloro-3,7,7-trimethyloct-4-en-1-yne

2. Write a complete mechanism for the addition of two equivalents of HBr to propyne. Show all intermediates, and explain whether or not Markovnikov's Rule applies to each addition.

3. Write a synthetic sequence that shows how to make cis-5-methyl-2-hexene. Allowable starting materials are acetylene and any alkyl halide or alcohol that has four carbons or fewer. You may also use any necessary solvents or inorganic reagents.