Introduction to organic synthesis laboratory

Lecture: 2 sessions over 4 weeks, 1 hour / session

Labs: 2 sessions / week, 4 hours / session

5.13 Organic Chemistry II

This course provides students with a research-inspired laboratory experience in which students carry out a short synthetic sequence including a catalytic asymmetric cycloaddition reaction. The experiment provides students with experience with a variety of advanced techniques for carrying out organic reactions including the use of air-sensitive reagents, distillation, recrystallization, and column chromatography. Analytical techniques include the use of chiral GC for determination of enantiomeric purity.

The key reaction in the experiment is the asymmetric Diels-Alder reaction of cylcopentadience with methacrolein. In principle four stereoisomeric [4+2] cycloaddition products can result from this reaction, so both diastereoselectivity and enantioselectivity are involved in determining the outcome of the reaction.

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