Solvent Polarity in SN1 and SN2 Reactions

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This Demonstration shows how the solvent polarity influences the nucleophilic substitution in both SN1 and SN2 reaction mechanisms [1].
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Contributed by: D. Meliga, V. Giambrone, L. Lavagnino and S. Z. Lavagnino (October 12)
With additional contributions by: F. Calcagno
(ITIS A. Artom, Asti)
Open content licensed under CC BY-NC-SA
Details
Snapshot 1: in an SN2 reaction, increasing solvent polarity changes the interactions between molecules of the reactants and the transition state; on the left an increase in the activation energies causes a decrease in the reaction rate; on the right, the opposite occurs
Snapshot 2: in an SN1 reaction, we can observe two maxima, showing the presence of two reaction pathways; only the first one is relevant to the reaction rate (bottleneck approximation) [1]
Snapshot 3: for the cases considered, the change in polarity does not appreciably affect the heat exchanged in the reactions
References
[1] S. Z. Lavagnino. Effetto solvente, nucleofilia reattività alogenuri alchilici [Video]. (Sep 14, 2023) www.youtube.com/watch?v=xK7BwLAbrIY&list=PLswwssc6Q2yYoP_INHmbmouyxW8oP _Gib&index=49.
[2] E. V. Anslyn and D. A. Dougherty, Modern Physical Organic Chemistry, Sausalito, CA: University Science, 2006.
Snapshots
Permanent Citation