1. Alcohols and amines are both nucleophilic. Explain why this reaction occurs to form Benadryl (diphenhydramine)

2. Outline a reasonable synthesis of the following:

3. Complete the short synthesis below by providing the necessary reagents.

4. An SN₂ reaction is characterized by inversion of configuration. Propose a sequence that would allow the preparation of the nitrile derivative B from bromide A. Note that there is no change in the overall stereochemistry of the product. More than one step may be required to complete the sequence.

5. Provide structures for compounds A-E, which are formed in the following reactions. Pay attention to stereochemistry where appropriate.