C. d. e. H H H H The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H 'H The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as He and Hc. Explain briefly.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter27: Amines
Section: Chapter Questions
Problem 5E
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This question deals with 4-aminobenzoic acid. 

There is a very broad
(almost flat) signal here.
14
B
Appears to be a singlet
Integration - 1
A
Integration - 2
HSP-04-502
12
10
- 00
8
ppm
9).
6
с
Integration - 2
D
Broad singlet
Integration - 2
2
-O
Transcribed Image Text:There is a very broad (almost flat) signal here. 14 B Appears to be a singlet Integration - 1 A Integration - 2 HSP-04-502 12 10 - 00 8 ppm 9). 6 с Integration - 2 D Broad singlet Integration - 2 2 -O
C.
d.
e.
H
H
H
H
H
The amine group is considered to be electron donating toward the ring by resonance, thus it
will place a partial negative charge on the (relative) ortho and para positions. Draw three
resonance structures for the product, showing the resulting charges at these positions.
H
H
H
H
The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place
a partial positive charge on the (relative) ortho and para positions. Draw three resonance
structures for the product, showing the resulting charges at these positions.
H
Based on the resonance structures, which of the aromatic protons is more shielded and
which is less shielded? Which of these protons will appear at the larger chemical shift and
which will appear at the lower chemical shift? Decide which of the protons should be labelled
as HB and Hc. Explain briefly.
Transcribed Image Text:C. d. e. H H H H H The amine group is considered to be electron donating toward the ring by resonance, thus it will place a partial negative charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H H H H The carboxylic acid is considered to be electron withdrawing by resonance, thus it will place a partial positive charge on the (relative) ortho and para positions. Draw three resonance structures for the product, showing the resulting charges at these positions. H Based on the resonance structures, which of the aromatic protons is more shielded and which is less shielded? Which of these protons will appear at the larger chemical shift and which will appear at the lower chemical shift? Decide which of the protons should be labelled as HB and Hc. Explain briefly.
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