If you were to try to do an EAS bromination reaction directly on aniline you would get a variety of products including ones in which two or more bromine atoms were incorporated onto the ring instead of only one. Why does this happen with aniline but not with acetanilide?

If you were to try to do an EAS bromination reaction directly on aniline you would get a variety of products including ones in which two or more bromine atoms were incorporated onto the ring instead of only one. Why does this happen with aniline but not with acetanilide?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 24E

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Question

NH₂
HN
μl z
0 °C
5 minutes
Scheme 2: Protection and bromination
NaBr; NACIO
Acetic Acid
Ethanol
0 °C to RT
15 minutes
HN
Br

. If you were to try to do an EAS bromination reaction directly on aniline you would get
a variety of products including ones in which two or more bromine atoms were
incorporated onto the ring instead of only one. Why does this happen with aniline but
not with acetanilide?

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