An hour after starting the reaction with an appropriate base, Din decides to monitor the reaction by TLC. His results are shown beside. While he remembered to spot both of the starting materials as reference spots, he forgot to label them, and now needs help analyzing the results. Show him the way by assigning each of the spots below, briefly explaining 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
Chapter24: Catalytic Carbon-carbon Bond Formation
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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.
)
Но
Base
+
Br
DMF/H20
ОН
NH2
Potential
1) КОН
2)
3) K2CO3
4) CSOH
5)
bases
b) An hour after starting the reaction with an appropriate base, Din
decides to monitor the reaction by TLC. His results are shown
beside. While he remembered to spot both of the starting materials
as reference spots, he forgot to label them, and now needs help
analyzing the results. Show him the way by assigning each of the
spots below, briefly explaining your answer.
DO
EO
во
Starting Starting Reaction
material
material
mixture
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. ) Но Base + Br DMF/H20 ОН NH2 Potential 1) КОН 2) 3) K2CO3 4) CSOH 5) bases b) An hour after starting the reaction with an appropriate base, Din decides to monitor the reaction by TLC. His results are shown beside. While he remembered to spot both of the starting materials as reference spots, he forgot to label them, and now needs help analyzing the results. Show him the way by assigning each of the spots below, briefly explaining your answer. DO EO во Starting Starting Reaction material material mixture
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