Chem 335 - Winter 2002
Organic Chemistry II
Dr. Carl C. Wamser
1. (2 pts) Give a complete IUPAC name for the following compound:
(S)-1-cyclohexylhex-4-yn-1-ol
2. (4 pts) Write a complete mechanism for the addition of HCl to propyne (two equivalents). Assume the reaction proceeds through carbocation intermediates. Show all steps, all resonance forms for any intermediates involved, and electron-pushing arrows.
3. (4 pts) Write a sequence of reactions that could be used to synthesize 2-bromopropane starting from acetylene and methyl iodide as the only organic materials. You may use any inorganic reagents or solvents that are needed.
