Lessons in stereochemistry from vegetable reduction of an aromatic di-ketone

CHED 1558

Bruce W. Baldwin, bbaldwin@arbor.edu, Department of Chemistry, Spring Arbor University, 106 E. Main St., Spring Arbor, MI 49283
Diastereomeric purity can be taught in the undergraduate chemical curriculum using vegetables as reductants, polarimetry for simple analysis and chiral GC for advanced analysis and hypothesis checking. This experiment contrasts the enantioselectivity of carrots and beets in mono- and di-reduction of a pro-chiral di-ketone. The student is able to start with easy analysis of a chiral alcohol/ketone and bridge to the more complicated possibilities presented by a chiral diol. Checking their understanding of enantiomers and diastereomers against polarimetry readings and more succinct chiral GC readings allows exploration of chirality at an undergraduate institution.