One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction. Once thereaction mixture has cooled, 1 mole of ethanol is added. Another vigorous exothermic reaction results. The mixture isanalyzed and found to contain triethylamine, ethyl acetate, and triethylammonium chloride. Propose mechanisms for thetwo exothermic reactions.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...
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One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction. Once the
reaction mixture has cooled, 1 mole of ethanol is added. Another vigorous exothermic reaction results. The mixture is
analyzed and found to contain triethylamine, ethyl acetate, and triethylammonium chloride. Propose mechanisms for the
two exothermic reactions.

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