Before you leave for Spring Break you will be required to turn in a Project Proposal that will include a detailed experimental procedure for your first week in lab. During the course of these projects, your group will share information with other groups working on the same project. At the end of the semester your group will present a short talk and submit a final written report. This report will determine a major portion of your lab grade. Sloop, J.C. J. Chem.
Piperine is a component of black pepper which causes sneezing.
Its presence in pepper was discovered many years ago, and its structure was elucidated near the beginning of the century. The synthesis starts with an allylic, radical halogenation to introduce a bromine atom. An Arbuzov reaction with triethyl phosphite displaces the bromine and produces a phosphonate that is then coupled to piperonal using a modified Wittig reaction. Hydrolysis of the ester, formation of the acid chloride using oxalyl chloride, and coupling to piperidine completes the synthesis. Ibuprofen is the active ingredient in a number of over the counter pain relievers, e.g. Advil, Motrin, and Nuprin.