While stereochemistry plays a pivotal role in the content of sophomore Organic Chemistry courses, application of stereochemistry in the teaching lab is typically hindered by the expense of many asymmetric reagents or the difficulty in clearly analyzing asymmetric products. Typical undergraduate experiments in stereochemistry involve the biological reduction of ketones such as ethyl acetoacetate or the synthesis of diastereomeric material via bromination of alkenes such as cis and trans-stilbenes. These experiments do little to reinforce the reactive chemistry of asymmetric carbons and the retention, inversion or racemization of carbon under different reaction conditions. A new experimental sequence has been developed to generate enantiomerically rich material from a novel biological reduction that can easily be carried out by undergraduate students. The material can then be used in a series of asymmetric transformations taught in the organic curriculum. Using the ideas of retention and inversion of stereocenters, enantiomeric ethers are generated and analyzed via different spectroscopic techniques. Implementation in a traditional organic chemistry laboratory section will also be discussed with student experimental results.

Novel stereochemistry experiment for sophomore organic chemistry lab

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.