a) Explain why the acetamido group is an ortho, para-directing group. Why should it be less effective in activating the aromatic ring toward further substitution than an amino group?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.6: Synthesis Of Amines
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a) Explain why the acetamido group is an ortho, para-directing group. Why should it be less
effective in activating the aromatic ring toward further substitution than an amino group?
b) o-Nitroaniline is more soluble in ethanol than p-nitroaniline. Propose a flow scheme by
which a pure sample of o-nitroaniline might be obtained from this reaction.
Transcribed Image Text:a) Explain why the acetamido group is an ortho, para-directing group. Why should it be less effective in activating the aromatic ring toward further substitution than an amino group? b) o-Nitroaniline is more soluble in ethanol than p-nitroaniline. Propose a flow scheme by which a pure sample of o-nitroaniline might be obtained from this reaction.
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