Methyl p-Nitrobenzoate

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter24: Carboxylic Acids & Derivatives
Section: Chapter Questions
Problem 3E
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2. In Experiment 4B, it was shown from the NMR spectrum that the meta-di-substituted Nitration product had
been recorded as a major product:
COOME
COOME
HNO3
H,SO,
NO2
Major product
However, there were two other possible but less favorable routes, i.e. ortho- or para- positions for the nitronium
to attack the aromatic ring with. Draw the H-NMR spectrum for Methyl p-Nitrobenzoate in case the
substitution takes place at the para-position. Pay attention to the chemical shift, the splitting pattern, and
approximate the integration in your spectra.
Methyl p-Nitrobenzoate
3.0
2.5
2.0
1.5 -
1.0-
0.5
4
3.
2
1.
10
6.
8.
Transcribed Image Text:2. In Experiment 4B, it was shown from the NMR spectrum that the meta-di-substituted Nitration product had been recorded as a major product: COOME COOME HNO3 H,SO, NO2 Major product However, there were two other possible but less favorable routes, i.e. ortho- or para- positions for the nitronium to attack the aromatic ring with. Draw the H-NMR spectrum for Methyl p-Nitrobenzoate in case the substitution takes place at the para-position. Pay attention to the chemical shift, the splitting pattern, and approximate the integration in your spectra. Methyl p-Nitrobenzoate 3.0 2.5 2.0 1.5 - 1.0- 0.5 4 3. 2 1. 10 6. 8.
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