Homework #8 Spring 2024
1. Molecule 3 was prepared via reaction of molecule 1 with hydrazine and base and forms intermediate 2 during this process. Provide a complete curved arrow mechanism for the most straightforward conversion to 3 from intermediate 2. You can use H2O+ as your acid and -
OH as your base.
2. Molecule 5 was prepared via molecule 4. Provide a complete curved arrow mechanism for the most straightforward conversion to 5. Use the reagents given for your mechanism.
3. For the following transformations draw the product in the box below. Draw only one stereoisomer in the box if there is more than one. On the right side check the box(es) that corresponds to the major product obtained from the reaction.
4. Provide two different pairs of starting materials needed to make the amine below via a reductive amination.
5. When the following reactions were performed, the corresponding products given were not obtained. Provide the correct organic molecules that would be isolated at the end of the reactions in the boxes below.
6. Propose a sequence of reactions that efficiently converts the given starting material(s) to the target molecule. Draw the structure of the product formed after each synthetic step. Do not write mechanisms.
Note: You do not need to show stereochemistry in your synthesis