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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Question
What is the hybridization of the nitrogen in aniline?
1. The nitrogen is sp2 hybridized.
2. The nitrogen is sp3 hybridized.
3. The nitrogen is between sp2 and sp3 hybridized, but closer to sp3.
4. The nitrogen is between sp2 and sp3 hybridized, but closer to sp2.
![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%2F0c96ac2a-388f-4e53-8456-e6fece572538%2F3bpadhl.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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