Preparation of the Diels-Alder product (3) ethyl acetate, rt, 168 h N-Ph Ph 1 3 2.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Need help providing an assignment for the 1H-NMR spectra provided for the Diels-Alder adduct 3 (mechanism included to show what 3 is) using the following table. Thank you :)

entry

chemical shift

integration

splitting

assignment

1

 

 

 

 

2

 

 

 

 

3

 

 

 

 

4

 

 

 

 

5

 

 

 

 

Preparation of the Diels-Alder product (3)
ethyl acetate, rt, 168 h
+
N-Ph
Ph
1
2
3
Transcribed Image Text:Preparation of the Diels-Alder product (3) ethyl acetate, rt, 168 h + N-Ph Ph 1 2 3
AA-DA
-120000
F110000
-100000
90000
-80000
-70000
F60000
50000
-40000
F30000
20000
10000
-0
F-10000
10.5
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
f1 (ppm)
4.5
4.0
3.5
3.0 2.5
2.0
1.5
1.0 0.5
0.0
7.4530
7.4351
-7.4315
-7.4194
-7.4157
-7.3814
-7.3782
-7.3750
7.3651
7.3597
7.3537
-7.3443
7.3412
7.2603
-7.1880
-7.1844
-7.1792
7.1664
600S'9-
r6.2930
9687'9-
.2818
IZU'
[3.2638
3.0129
-90°7 -
1600'E-
Z500'S
-2.0437
.6772
809S'I-
-1.4348
79/7'I
1.2583
Transcribed Image Text:AA-DA -120000 F110000 -100000 90000 -80000 -70000 F60000 50000 -40000 F30000 20000 10000 -0 F-10000 10.5 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 f1 (ppm) 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 7.4530 7.4351 -7.4315 -7.4194 -7.4157 -7.3814 -7.3782 -7.3750 7.3651 7.3597 7.3537 -7.3443 7.3412 7.2603 -7.1880 -7.1844 -7.1792 7.1664 600S'9- r6.2930 9687'9- .2818 IZU' [3.2638 3.0129 -90°7 - 1600'E- Z500'S -2.0437 .6772 809S'I- -1.4348 79/7'I 1.2583
Expert Solution
Step 1

Number of signals in 1H NMR: Tells us how many sets of protons with different electronic environment there are in the molecule.

Chemical shift: Tells us about electronic environment

Integration: Corresponds to the number of protons giving rise to the signal

Multiplicity of signal: Tells us about neighboring group

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