2. Draw the complete mechanism for the following reactions, showing the formation of each product. Include all formal charges, electron-pushing arrows, and resonance structures. a. b. Et NO₂ Br Me. Me CI 1. NaOH, H₂O, heat 2. H₂O* 1 major product 1. NaOH, H₂O, 300 °C 2. H₂O* (acidic work-up) Hint: Show Meisenheimer complex (intermediates stabilized by resonance) 3 major products BITE o eM u8 9

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 45E
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2. Draw the complete mechanism for the following reactions, showing the formation of each
product. Include all formal charges, electron-pushing arrows, and resonance structurac
a.
b.
Et
NO₂
Br
Me. Me
1. NaOH, H₂O,
heat
2. H₂O*
CI
1 major product
1. NaOH, H₂O,
300 °C
2. H₂O*
(acidic work-up)
Hint: Show Meisenheimer complex
(intermediates stabilized by resonance)
TeoM
3 major products
HAM
amenn
O
eM
181
9
Transcribed Image Text:2. Draw the complete mechanism for the following reactions, showing the formation of each product. Include all formal charges, electron-pushing arrows, and resonance structurac a. b. Et NO₂ Br Me. Me 1. NaOH, H₂O, heat 2. H₂O* CI 1 major product 1. NaOH, H₂O, 300 °C 2. H₂O* (acidic work-up) Hint: Show Meisenheimer complex (intermediates stabilized by resonance) TeoM 3 major products HAM amenn O eM 181 9
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