title: Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate H NMR Experiment To Introduce Chiral Chemistry.
abstract: This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is catalyzed by acylase I. The unreacted alcohol is then treated with a chiral acid and the resulting ester diastereomer is analyzed by NMR. This experiment is suitable for group work in the laboratory as several diastereomers are synthesized and compared to determine which enantiomer of 1-phenylethanol reacts with the enzyme.
authors.affiliation: Department of Chemistry, Doane College, Crete, Nebraska 68333.
authors.forename: David H
authors.initials: DH
authors.lastname: Smith
authors.forename: Mark
authors.initials: M
authors.lastname: Wilson
authors.forename: Kyla
authors.initials: K
authors.lastname: Ronhovde
authors.forename: Erin
authors.initials: E
authors.lastname: Wilson
authors.forename: David
authors.initials: D
authors.lastname: Clevette
authors.forename: Kerry
authors.initials: K
authors.lastname: Lucas
authors.forename: Andrea
authors.initials: A
authors.lastname: Holmes