1). Propose a mechanism for the Swern oxidation using the reagents shown.

2). Suggest how to carry out the following transformations. You should use reagents that will be selective (i.e., regioselective, diastereoselective, use protecting groups if necessary). Each transformation may take a few steps.

In all cases, the product is on the right hand side!

a) 

b) 

d) 

3). Suggest 2 different routes to synthesizing this compound (i.e., 2 different initial bond disconnections). The starting material may be any size but can only contain 2 functional groups. Each route should only involve 1-3 steps. (LOOK UP YOUR NOTES FROM LAST YEAR ON ALDOL AND ENOLATE CONDENSATIONS).

4). Show a reasonable disconnection for this molecule, which is a fragment in a compound called Salinomycin (no need for specific reactions, for each disconnection show acceptor (a) and donor (d). For the purposes of this course, in a Diels-Alder reaction, the diene is the donor, the dienophile is the acceptor). (Hint: if you open the ring at the oxygen in the first disconnection life will get easier).

5). Show the 5 most acidic protons on the molecule and give the approximate pKa values for each.
 

6). Suggest how to undertake the following conversions. (Hint: how could you protect a diol?)