Both 3-chloronitrobenzene and 4-chloronitrobenzene undergo nucleophilic aromatic substitution reactions with hydroxide to give the corresponding nitrophenols:

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.46P
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Both 3-chloronitrobenzene and 4-chloronitrobenzene undergo nucleophilic
aromatic substitution reactions with hydroxide to give the corresponding
nitrophenols:
ČI
он
HO
CH
+
NO2
NO2
3-chloronitro phenol
он
HO
NO2
NO2
4-chloronitro phenol
The second of these two reactions is found to proceed at a higher rate, when
carried out under identical conditions. By considering the stabilities of any
intermediates that can form, explain this difference in reactivity
Transcribed Image Text:Both 3-chloronitrobenzene and 4-chloronitrobenzene undergo nucleophilic aromatic substitution reactions with hydroxide to give the corresponding nitrophenols: ČI он HO CH + NO2 NO2 3-chloronitro phenol он HO NO2 NO2 4-chloronitro phenol The second of these two reactions is found to proceed at a higher rate, when carried out under identical conditions. By considering the stabilities of any intermediates that can form, explain this difference in reactivity
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