Carey, end-of-chapter problems
ARIS problems

b)

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.