I am looking at this unknown NMR sheet, and I am trying to identify an amine/aldehyde. I also have the IR sheet, but I should be able to figure that out once I have the identity of the unknown. I think it is an aniline with an ether, but I am not sure and don't know all the steps to take when looking at an NMR. Could you explain what I am looking at? Thank you!

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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I am looking at this unknown NMR sheet, and I am trying to identify an amine/aldehyde. I also have the IR sheet, but I should be able to figure that out once I have the identity of the unknown. I think it is an aniline with an ether, but I am not sure and don't know all the steps to take when looking at an NMR. Could you explain what I am looking at? Thank you!

Bb Exp 02 - Reductive Amination - 2 x
Bb *13748443
A unknown NMR.pdf
O File | C:/Users/Seren/Downloads/unknown%20NMR.pdf
+
1
of 2
(D Page view
A Read aloud
O Add text | V Draw
99
E Highlight
O Erase 6
One
pronen
Jevetuns
One
Iprodons
2
prolors
2
6.
8.
2
7
6
5
Aromatic
Ring
3
ether 2
PPM
P Type here to search
6:44 PM
2/15/2022
-Co
Transcribed Image Text:Bb Exp 02 - Reductive Amination - 2 x Bb *13748443 A unknown NMR.pdf O File | C:/Users/Seren/Downloads/unknown%20NMR.pdf + 1 of 2 (D Page view A Read aloud O Add text | V Draw 99 E Highlight O Erase 6 One pronen Jevetuns One Iprodons 2 prolors 2 6. 8. 2 7 6 5 Aromatic Ring 3 ether 2 PPM P Type here to search 6:44 PM 2/15/2022 -Co
A
F
G
H.
K.
caps lock
pause
shift 1
C
V
M.
1377
1713.51cm-1, 134.07%T
130-
120-
1187.18cm-1, 109.11%T
110-
606.55cm-1, 106.66%T
735.66cm-1103.32%T
2036.31cm104,62A 93cm-1, 101.34%T
2958.96cm-6244cm-1,2634%dm-1, 99-28%1
1640.93cm-1.101.34%T
1385.72cm-1, pp.32%T
100-
90-
80-
70-
60
50-
594.89cm-1, 53.15%T
11369.43cm-1 5.58%T
725.92cm-1, 49.43%T
823.98cm-1, 43.72%T
1547 3 cm-1, 48.10 T
40-
1525.58cm-1, 40.53%
'1230.46cm-1, 38.95%T
1162.46cm-1, 36.53%
30-
1592.20cm-1, 32.46%T
810.95cm-1, 19.63%T
20
17+
4000
2000
cm-1
3500
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%T
Transcribed Image Text:A F G H. K. caps lock pause shift 1 C V M. 1377 1713.51cm-1, 134.07%T 130- 120- 1187.18cm-1, 109.11%T 110- 606.55cm-1, 106.66%T 735.66cm-1103.32%T 2036.31cm104,62A 93cm-1, 101.34%T 2958.96cm-6244cm-1,2634%dm-1, 99-28%1 1640.93cm-1.101.34%T 1385.72cm-1, pp.32%T 100- 90- 80- 70- 60 50- 594.89cm-1, 53.15%T 11369.43cm-1 5.58%T 725.92cm-1, 49.43%T 823.98cm-1, 43.72%T 1547 3 cm-1, 48.10 T 40- 1525.58cm-1, 40.53% '1230.46cm-1, 38.95%T 1162.46cm-1, 36.53% 30- 1592.20cm-1, 32.46%T 810.95cm-1, 19.63%T 20 17+ 4000 2000 cm-1 3500 3000 2500 1500 1000 450 %T
Expert Solution
Step 1

According to the IR values: sharp peak at 1592 cm-1 and broad spectrum around 2800-3000 cm-1 ; both of these values indicate the presence of a amide (-CONH) group in the compound. 

The 1H NMR spectrum depicts the structure of the compound.

The chemical shift values of the specified proton (corelate with the given images and structure of the compound) has been given below:

a: δ (ppm) 0.9 (6H, d)

b: δ (ppm) 1.6 (1H, multiplate)

c: δ (ppm) 2.5 (2H, d)

d: δ (ppm) 4.2 (1H, s)

e: δ (ppm) 3.6 (2H, s)

f: δ (ppm) 3.0 (6H, s)

g: δ (ppm) 7.2 (2H, d)

h: δ (ppm) 6.8 (2H, d)

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