Allegheny Chemistry
 


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Allegheny College
Department of Chemistry
520 N. Main Street
Meadville, PA 16335
814-332-5363

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The Goal

Your goal is to convert 4-methylvaleric acid (3) into the single enantiomer of the chiral aldehyde 8 (numbers correspond to the journal article). To assist you in this endeavor, you will receive 0.500 g of the chiral auxiliary shown below. Notice that your journal article uses the oxazolidinone with R=isopropyl. You will need to account for the difference in molecular weight, but the rest of the chemistry will be the same.

The Challenge
You have all the information you need in the literature article. You will have to adjust for the different auxiliary and for the smaller scale. This must be done before you walk into lab. Planning is everything. Groups that continually lose time in lab from poor planning will be assessed accordingly. On the other hand, obtaining compound 8 is not absolutely necessary for success--if your lab work is well-planned and effective, if all the compounds along the way are obtained in reasonable yield and in high purity, you have exhibited the behavior of a conscientious research chemist, which is the ultimate goal of this experience.


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