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One mole of acetyl chloride is added to a liter of
Chapter 15, Problem 56SP(choose chapter or problem)
Problem 56SP
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.
Questions & Answers
QUESTION:
Problem 56SP
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.
ANSWER:
Solution:
Here we have to propose mechanisms for the two given exothermic reactions i.e:-
1.Reaction between triethyl amine and acetyl chloride
2.Reaction between the product form from the above reaction and ethanol
Step 1
1.Reaction between triethyl amine and acetyl chloride
Acetyl chloride on addition with triethyl amine forms a salt instead of an amide because the triethylamine is a nucleophile and no H-atom is bonded to it. In this nucleophilic addition reaction , it loses one chlorine molecule and forms 1-triethylamine ethanone.
(Acid chloride) (triethylamine) (Intermediate) (1-triethylamine ethanone)