Previously, we presented a discovery-based Grignard experiment aimed at the second-semester organic chemistry (OCHEM II) laboratory curriculum, wherein an asymmetrical, tertiary alcohol, 1-(4-methoxyphenyl)-2-methyl-1-phenylpropan-1-ol, was synthesized using three different Grignard reactions. The efficiency of each reaction was assessed in terms of cost, time, and purity of product via GC-MS, IR and <sup>1</sup>H NMR spectroscopic analyses. The goal of the current project was to perform computational simulations to calculate transition state energy differences for each of these three Grignard reactions, in order to resolve observed differences in the reactivities with the structures of the reagents. The activation energy (E<sub>a</sub>) was calculated using density functional theory (DFT). Computer simulations were done using the transition state calculation available in DMol3 with a 0.02 Hartree/Å convergence threshold. The energy difference between the reactants and the activated complex (transition state) was extracted and compared for each mechanism. The development of this project has prompted its potential incorporation into the physical chemistry (PCHEM) laboratory curriculum here at UNG. By linking outcomes from the OCHEM II discovery-based Grignard experiment with more advanced concepts taught in PCHEM, upper-level chemistry majors will be able to see how computational simulations complement experimental findings.

Using computational simulations to reconcile observed reactivity differences in Grignard reactions

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.