Question 9: Select all of the terms that could be used to describe sodium methoxide. (MORE than one answer) base acid electrophile

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter25: Enolate & Enol Nucleophiles
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Question 9: Select all of the terms that could be used to describe sodium methoxide. (MORE than one answer)

base

acid

electrophile

nucleophile

Na OCH3
N.
???
N.
Gwen set up the reaction shown above. She started with 1.5 g of the p-acetamidophenol and added exactly 1.0 molar equivalents of the sodium methoxide. Her solvent was
ethanol (100%). After letting the mixture stir for 10 minutes, Gwen then added 1.3 molar equivalents of the alkyl bromide. She let the reaction heat at reflux for 30 minutes,
then slowly cooled it to room temperature. During the course of the reflux, she noticed that a white solid formed until it there was enough to coat the sides of the flask. After
the solution was cooled, she added 10 mL of water to the reaction mixture. When she did that, the solid disappeared. Next, Gwen cooled the mixture on ice. A different solid
(one that looked like shiny glitter) appeared during the cooling process.
Transcribed Image Text:Na OCH3 N. ??? N. Gwen set up the reaction shown above. She started with 1.5 g of the p-acetamidophenol and added exactly 1.0 molar equivalents of the sodium methoxide. Her solvent was ethanol (100%). After letting the mixture stir for 10 minutes, Gwen then added 1.3 molar equivalents of the alkyl bromide. She let the reaction heat at reflux for 30 minutes, then slowly cooled it to room temperature. During the course of the reflux, she noticed that a white solid formed until it there was enough to coat the sides of the flask. After the solution was cooled, she added 10 mL of water to the reaction mixture. When she did that, the solid disappeared. Next, Gwen cooled the mixture on ice. A different solid (one that looked like shiny glitter) appeared during the cooling process.
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