Q.The angle found in p-nitroaniline means that the amine group is planar and in the same plane as the benzene ring. Why is this the case?1. The nitro group withdraws the lone pair electrons from the amine, primarily via induction, making the N atom sp2 hybridized and hence trigonal planar.2. The nitro group withdraws the lone pair electrons from the amine, primarily via resonance, making the N atom sp2 hybridized and hence trigonal planar.3. The lone pair of the N atom of the NH2 must be in a p orbital to make the system aromatic.4. The nitrogen of an amine is usually planar, and aniline and methylamine are exceptions. The-NH, group in aniline is not completely planarwith the benzene ring. Specifically, the angle to thebenzene ring and the bisector of the amino group is140° instead of 180°. By comparison, the analogousangle in methylamine is 125°, while in p-nitroaniline itis indeed 180°.H,C-NHHAH140°180125AnilineMethylaminep-Nitroaniline

In p-nitroaniline, the nitro group has a -R effect on the ring and it indirectly withdraws the…

Answered: The-NH, group in aniline is not…

Organic Chemistry

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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

Chapter27: Amino Acids And Proteins

Section: Chapter Questions

Problem 27.39P: A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug...

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Q.The angle found in p-nitroaniline means that the amine group is planar and in the same plane as the benzene ring. Why is this the case?

1. The nitro group withdraws the lone pair electrons from the amine, primarily via induction, making the N atom sp² hybridized and hence trigonal planar.

2. The nitro group withdraws the lone pair electrons from the amine, primarily via
resonance, making the N atom sp² hybridized and hence trigonal planar.

3. The lone pair of the N atom of the NH₂ must be in a p orbital to make the system aromatic.

4. The nitrogen of an amine is usually planar, and aniline and methylamine are exceptions.

The-NH, group in aniline is not completely planar
with the benzene ring. Specifically, the angle to the
benzene ring and the bisector of the amino group is
140° instead of 180°. By comparison, the analogous
angle in methylamine is 125°, while in p-nitroaniline it
is indeed 180°.
H,C-N
H
HA
H
140°
180
125
Aniline
Methylamine
p-Nitroaniline

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