This undergraduate organic laboratory experiment complements previously described and popular experiments on hydration of 1-hexene where students experimentally establish the Markovnikov regioselectivity of alkene hydration. In this experiment, students explore not only the regiochemistry but also the stereochemistry of 1-hexene hydration and obtain spectral evidence that hydration of 1-hexene yields 2- and 3-hexanols as major products and that these chiral alcohols are obtained as racemic mixtures. This objective is achieved by converting commercial samples of racemic 2- and 3-hexanols to diastereomeric camphorsulfonate esters using commercial samples of enantiomerically pure (1S)-(+)-10-camphorsulfonyl chloride. The product directly obtained from hydration of 1-hexene is also esterified using the same reagent. 1H and 13C NMR spectra of the products from each reaction are then obtained, analyzed, and compared. Thus, students determine the composition of the diastereomeric mixtures. The results lead to a postlab discussion of NMR spectroscopic analysis of enantiomers and diastereomers, stereochemical relationships between faces of planar species such as carbocations, and the effect of a chiral auxiliary on a racemate. Most importantly, students experimentally prove one of the main doctrines of organic stereochemistry whereby racemates are always produced from reactions of achiral starting materials that afford chiral products.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.