2. The compound 4-methylanisole, E, was subjected to the Birch reduction reagents and rather than producing a single product it produced two isomers, F and G. OCH3 a. b. E 1. Li, NH3 t-BuOH, THF 2. aq HCI THF F 30% + G 70% Propose a mechanism to illustrate the formation of both F and G. Explain why the major and minor product distribution is observed.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter21: Nas: Nucleophilic Aromatic Substitution
Section: Chapter Questions
Problem 7E
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2. The compound 4-methylanisole, E, was subjected to the Birch reduction reagents
and rather than producing a single product it produced two isomers, F and G.
OCH3
a.
b.
E
1. Li, NH3
t-BuOH, THF
2. aq HCI
THF
F
30%
+
G
70%
Propose a mechanism to illustrate the formation of both F and G.
Explain why the major and minor product distribution is observed.
Transcribed Image Text:2. The compound 4-methylanisole, E, was subjected to the Birch reduction reagents and rather than producing a single product it produced two isomers, F and G. OCH3 a. b. E 1. Li, NH3 t-BuOH, THF 2. aq HCI THF F 30% + G 70% Propose a mechanism to illustrate the formation of both F and G. Explain why the major and minor product distribution is observed.
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