Abstract
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).
Published Version
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