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Kinetic and Thermodynamic Control of Electrophilic Addition Reactions

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This Demonstration shows the effect of thermodynamics and kinetics on electrophilic addition reactions producing dienes. The following reaction is considered:

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Reaction progress can be viewed using the "time" slider; the quantities of the products are proportional to the size of the balls. Using the "reactions" buttons, it is possible to choose a reaction and follow its progress. Use the checkbox to visualize the thermal energy of the molecules and compare it to the activation energies.

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Contributed by: D. Meliga and S. Z. Lavagnino (March 2018)
Open content licensed under CC BY-NC-SA

Snapshots

Details

Snapshot 1: the lower thermal energy promotes the predominance of the 1,2-addition compared to the 1,4-addition

Snapshot 2: the higher thermal energy promotes the predominance of the 1,4-addition compared to the 1,2-addition

Snapshot 3: increasing the temperature causes the transfer of the double bond

References

[1] R. T. Morrison and R. N. Boyd, Organic Chemistry, 3rd ed., Boston: Allyn and Bacon, 1973.

[2] Chemistry LibreTexts. "16.10: Electrophilic Addition: 1,2- versus 1,4-Addition." (Feb 16, 2018) chem.libretexts.org/?title=Textbook_Maps/Organic_Chemistry_Textbook_Maps/Map:_Organic_Chemistry_(Smith)/Chapter_16:_Conjugation,_Resonance,_%26_Dienes/16.10:_Electrophilic_Addition:_1,2-_Versus_1,4-Addition.

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