Question

We're going over the reactions involving Alkenes and Alkynes. However, I'm extremely confused I how to determine with solvent/solvents to use and also when already given the solvents with the reactants how this will effect the products. I studied the basic mechanisms for all the reactions, but when given quizzes in class the solvents aren't always the same or have more parts.

For example:
3 octanol plus 1. TsCl 2. KCN yields ?

1, 1, 2 trimethylcyvlohexane (excess) plus Br2, hv yields. ?

Like I said. I think being able to recognize the solvents in relation to with mechanism to follow is my biggest battle here, I don't even know where to look for this information.