In this assignment you may use your notes or your textbook. You may consult with a classmate, but you must indicate this in the page you turn in, though this will not affect your grade. You may not turn in any answer which you do not fully understand.

For each of the following problems, draw the set of reactions which would lead to the desired target in high yield. You may begin with any needed alcohols with four carbons or fewer, any needed inorganic reagents, special reagents (e.g. PCC, triphenylphosphine), solvents, or catalysts.

1. Use a Wittig method to prepare 3-heptene. Hint: first you'll have to prepare the needed starting materials for the Wittig method from your allowed starting materials.

2. Starting with the following bromoester, outline the Reformatsky synthesis of the target shown. Hint: remember, once the Reformatsky reaction is finished, you can do more reactions to convert that product to the desired target.

3. Show how your starting materials, the Grignard reaction, and the Baeyer-Villiger oxidation can yield the following target. Again, you will need to convert your starting materials into something useful for the Grignard reaction before you can make any progress.