Din Diarin wants to methylate the diphenol shown below using methyl bromide. The reaction is a simple nucleophilic substitution, and requires both phenol groups to be deprotonated by a base so that the resulting phenoxide may attack the alkyl halide and form a C-O bond. но. Base + 2 Br DMF/H20 ОН NH2 Potential bases 1) КОН 3) K2CO3 4) CSOH 5) a) Which of the potential base(s) would likely be an acceptable choice to ensure an efficient reaction under the current reaction conditions? Briefly explain your answer.

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 19.57P
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Din Diarin wants to methylate the diphenol shown below using methyl bromide. The
reaction is a simple nucleophilic substitution, and requires both phenol groups to be
deprotonated by a base so that the resulting phenoxide may attack the alkyl halide and
form a C-O bond.
HO
Base
+
Br
DMF/H20
ОН
NH2
Potential
bases
1) КОН
2)
3) K2CO3
4) CSOH
5)
a) Which of the potential base(s) would likely be an acceptable choice to ensure an
efficient reaction under the current reaction conditions? Briefly explain your answer.
Transcribed Image Text:Din Diarin wants to methylate the diphenol shown below using methyl bromide. The reaction is a simple nucleophilic substitution, and requires both phenol groups to be deprotonated by a base so that the resulting phenoxide may attack the alkyl halide and form a C-O bond. HO Base + Br DMF/H20 ОН NH2 Potential bases 1) КОН 2) 3) K2CO3 4) CSOH 5) a) Which of the potential base(s) would likely be an acceptable choice to ensure an efficient reaction under the current reaction conditions? Briefly explain your answer.
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