This laboratory exercise is incorporated into the second semester organic chemistry laboratory series after students have been exposed to spectroscopy and numerous reaction mechanisms. The experiment has three objectives: to provide direct experience preparing and running an NMR sample, to experimentally confirm a common reaction mechanism and to strengthen the students’ ability to interpret splitting patterns with 1H-NMR spectra. This experiment makes use of the reduction of a ketone, 3-hydroxy-acetaphenone, to an alcohol, 3-hydroxy-1-phenylethanol using sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4). Each pair of students performs a reduction reaction with either protonated or deuterated conditions. Pairs of students then combine into groups of 4 to compare spectral data. Students observe the change in the splitting pattern caused by deuterium incorporation into the alcohol product and confirm the reaction mechanism.

Applying splitting patterns in 1H-NMR to evaluate a reaction mechanism

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.