Resumen de Addition of “HOBr” to trans-Anethole: Investigation of the Regioselectivity and the Stereoselectivity of an Addition Reaction
Brad Andersh, Wayne B. Bosma, Margaret K. Hammar, Jessica A. Graves, Kathryn N. Moon, Chareese R. Newborn
In this advanced organic experiment, students used a combination of spectroscopy and molecular modeling to determine the regiochemical and stereochemical outcome of the addition of “HOBr” to trans-anethole. 1H, 13C, and HMQC NMR spectra were used to determine the regiochemistry of the addition reaction, and coupling-constant analysis and molecular modeling were used to determine the stereochemistry. Using a procedurally simple synthetic procedure, students obtained a racemic mixture of (1S,2R)- and (1R,2S)-2-bromo-1-(4-methoxyphenyl)propan-1-ol in 70% quantitative yield from the reaction between trans-anethole and N-bromosuccinimide (NBS) in 95% acetone(aq).
