Chem 335 - Winter 2002
Organic Chemistry II
Dr. Carl C. Wamser
Carey, pages 358-364:
Problems 9.18 - 9.35
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.
