2. This question deals with the product formed in this experiment ethyl 4-aminobenzoate. a. For the IR spectrum shown below, identify the structural features which cause each of the major IR signals. (You will have to decide which of the signals are considered important enough to be considered to be "major" - essentially you should look at the higher energy region je, above than the fingerprint region.) % Transmittance 20 40 60 100 80 0. 4000 3600 3000 2500 2000 1500 1000 Wavenumber (cm)

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Chapter1: Chemical Foundations
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2.
This question deals with the product formed in this experiment ethyl 4-aminobenzoate.
a.
For the IR spectrum shown below, identify the structural features which cause each of the
major IR signals. (You will have to decide which of the signals are considered important
enough to be considered to be "major" - essentially you should look at the higher energy
region je, above than the fingerprint region.)
% Transmittance
20
40
60
100
80
0
4000
3600
3000
2:500
2000
1500
1000
Wavenumber (cm)
Transcribed Image Text:2. This question deals with the product formed in this experiment ethyl 4-aminobenzoate. a. For the IR spectrum shown below, identify the structural features which cause each of the major IR signals. (You will have to decide which of the signals are considered important enough to be considered to be "major" - essentially you should look at the higher energy region je, above than the fingerprint region.) % Transmittance 20 40 60 100 80 0 4000 3600 3000 2:500 2000 1500 1000 Wavenumber (cm)
b.
For the NMR spectrum shown below, draw the structure of the compound next to the spectrum
and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the
Chemical shift, integration and multiplicity in the table. You should consider electron donating
and withdrawing effects before assigning the aromatic ring protons.
Ε
B
C and D
E
Note that the actual measured integration values are given above each set of peaks.
Also note that the signal from -3.8-4.5 ppm is due to two overlapping signals;
A quartet (C) and a very broad singlet (D).
Each of these two signas has an integration of approximately 2.0
(the total integration for this combined signal is approximately 4.0 (actual -3.851))
STRUCTURE:
Proton label
Chemical shift Relative Integration Expected (& Multiplicity
(ppm)
observed)
C.
The NMR spectrum shown
A
B
C
D
E
below represents the product (ethyl 4-aminobenzoate) after it has been shaken with deuterium oxide (D₂O).
Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate. Draw the
structure of the compound next to the spectrum and label the protons so that they match the letter labels
shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table.
D. on the results of the "D20 shake". What happened to the signal which had been caused by HD?
Explain briefly.
Transcribed Image Text:b. For the NMR spectrum shown below, draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table. You should consider electron donating and withdrawing effects before assigning the aromatic ring protons. Ε B C and D E Note that the actual measured integration values are given above each set of peaks. Also note that the signal from -3.8-4.5 ppm is due to two overlapping signals; A quartet (C) and a very broad singlet (D). Each of these two signas has an integration of approximately 2.0 (the total integration for this combined signal is approximately 4.0 (actual -3.851)) STRUCTURE: Proton label Chemical shift Relative Integration Expected (& Multiplicity (ppm) observed) C. The NMR spectrum shown A B C D E below represents the product (ethyl 4-aminobenzoate) after it has been shaken with deuterium oxide (D₂O). Write the equation for the reaction which occurs when D₂O reacts with ethyl 4-aminobenzoate. Draw the structure of the compound next to the spectrum and label the protons so that they match the letter labels shown on the NMR spectrum. Fill in the Chemical shift, integration and multiplicity in the table. D. on the results of the "D20 shake". What happened to the signal which had been caused by HD? Explain briefly.
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