This was a Diels-Alder on Water lab where we combined 9-anthracenemethanol and N-methylmaleimide to make the Diels-Alder Adduct. I provided you with the NMR, the observed peaks from left to right, and a table that could be helpful. Which functional group represents each peak? Observed Peaks 7.08 ppm 5.28 ppm 3.33 ppm 2.52 ppm 2.14 ppm 1.63 ppm

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This was a Diels-Alder on Water lab where we combined 9-anthracenemethanol and N-methylmaleimide to make the Diels-Alder Adduct. I provided you with the NMR, the observed peaks from left to right, and a table that could be helpful. Which functional group represents each peak?

Observed Peaks 7.08 ppm 5.28 ppm 3.33 ppm 2.52 ppm 2.14 ppm 1.63 ppm
TABLE 9.1 APPROXIMATE PROTON CHEMICAL SHIFTS
Type of Proton
1° Alkyl, RCH3
2° Alkyl, RCH₂R
3° Alkyl, R3CH
Allylic, R₂C=C-CH3
R
Ketone, RCCH3
ROCH3
Benzylic, ArCH3
Acetylenic, RC=CH
Alkyl iodide, RCH₂I
Ether, ROCH₂R
Alcohol, HOCH₂R
Chemical Shift
(8, ppm)
0.8-1.2
1.2-1.5
1.4-1.8
1.6-1.9
2.1-2.6
2.2-2.5
2.5-3.1
3.1-3.3
3.3-3.9
3.3-4.0
Type of Proton
Alkyl bromide, RCH₂Br
Alkyl chloride, RCH₂CI
Vinylic, R₂C=CH₂
Vinylic, R₂C=CH
R
Aromatic, ArH
Aldehyde, RCH
RCH
Alcohol hydroxyl, ROH
Amino, R-NH₂
Phenolic, ArOH
Carboxylic, RÇOH
ag
Chemical Shift
(8, ppm)
3.4-3.6
3.6-3.8
4.6-5.0
5.2-5.7
6.0-8.5
9.5-10.5
0.5-6.09
1.0-5.0a
4.5-7.79
10-13ª
"The chemical shifts of these protons vary in different solvents and with temperature and concentration.
Transcribed Image Text:TABLE 9.1 APPROXIMATE PROTON CHEMICAL SHIFTS Type of Proton 1° Alkyl, RCH3 2° Alkyl, RCH₂R 3° Alkyl, R3CH Allylic, R₂C=C-CH3 R Ketone, RCCH3 ROCH3 Benzylic, ArCH3 Acetylenic, RC=CH Alkyl iodide, RCH₂I Ether, ROCH₂R Alcohol, HOCH₂R Chemical Shift (8, ppm) 0.8-1.2 1.2-1.5 1.4-1.8 1.6-1.9 2.1-2.6 2.2-2.5 2.5-3.1 3.1-3.3 3.3-3.9 3.3-4.0 Type of Proton Alkyl bromide, RCH₂Br Alkyl chloride, RCH₂CI Vinylic, R₂C=CH₂ Vinylic, R₂C=CH R Aromatic, ArH Aldehyde, RCH RCH Alcohol hydroxyl, ROH Amino, R-NH₂ Phenolic, ArOH Carboxylic, RÇOH ag Chemical Shift (8, ppm) 3.4-3.6 3.6-3.8 4.6-5.0 5.2-5.7 6.0-8.5 9.5-10.5 0.5-6.09 1.0-5.0a 4.5-7.79 10-13ª "The chemical shifts of these protons vary in different solvents and with temperature and concentration.
Amplitude
1200-
1000
800
600-
400
200
12
Data saved in "c:\projects\data\2023\@g\24\164326"
10
8
||
T₁
Spectrum Scan [1/1]
9.40
6
کر
2.43
ppm
E
11
- 2.52
1.60
-2.14
یلسند
کرا
3.00
1.08
-1.63
2
2.65
START
7.63
5.29
3.49
2.71
2.23
1.80
0
END
6.83
4.52
3.11
2.31
2.00
1.44
VALUE
9.40
2.43
1.60
3.00
1.08
2.65
-2
Transcribed Image Text:Amplitude 1200- 1000 800 600- 400 200 12 Data saved in "c:\projects\data\2023\@g\24\164326" 10 8 || T₁ Spectrum Scan [1/1] 9.40 6 کر 2.43 ppm E 11 - 2.52 1.60 -2.14 یلسند کرا 3.00 1.08 -1.63 2 2.65 START 7.63 5.29 3.49 2.71 2.23 1.80 0 END 6.83 4.52 3.11 2.31 2.00 1.44 VALUE 9.40 2.43 1.60 3.00 1.08 2.65 -2
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