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
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
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
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
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
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F3491e5f9-c7fa-4848-ae4f-9ad1bf294bd6%2F68734318-838f-4ee3-ab1d-cb2dd2d0c922%2Fk5qcx56.jpeg&w=3840&q=75)
Transcribed Image Text: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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