How many protons are in this molecule? How many carbons in this molecule? What is the molecular formula and degree of unsaturation for this compound?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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Your graduate student mentor in the organic chemistry lab you work in is out of town on a
ski trip and has tasked you with characterizing an unknown side product. Using the
following spectral information you collected below, please answer the following questions
and determine the structure of this compound.
Predicted 1H NMR-Spectrum
7.5
f
A (d)
7.34
Predicted 13C NMR Spectrum
160
1
1
7.0
A (s)
156.12
B (d)
6.87
H
6.5
150
6.0
140
C (8)
129.52
B (s)
132.42
5.5
130
D (s)
12074
5.0
120
4.5
f1 (ppm)
¹H NMR (500 MHz, Chloroform-d): 67.34 (d, J = 8.2 Hz, 1H), 6.87 (d, J = 8.2 Hz, 1H), 1.22 (s, 4.5H)
110
100
f1 (ppm)
4.0
90
How many carbons in this molecule?
How many protons are in this molecule?
3.5
80
1
E (s)
77.99
3.0
70
2.5
60
2.0
50
1.5
40
車
10,12
F(s)
28 50
30
1.0
1
2
0.5
F0.3
0.2
-0.0
0.5
-0.4
-0.3
0.2
-0.1
13C NMR (125 MHz, Chloroform-d): 156.1, 132.4, 129.5, 120.7, 78.0, 28.5
MS: 184.07 m/z (100.0%), 186.06 m/z (32.0%), 185.07 m/z (11.0%), 187.07 m/z (3.5%)
0.0
What is the molecular formula and degree of unsaturation for this compound?
Transcribed Image Text:Your graduate student mentor in the organic chemistry lab you work in is out of town on a ski trip and has tasked you with characterizing an unknown side product. Using the following spectral information you collected below, please answer the following questions and determine the structure of this compound. Predicted 1H NMR-Spectrum 7.5 f A (d) 7.34 Predicted 13C NMR Spectrum 160 1 1 7.0 A (s) 156.12 B (d) 6.87 H 6.5 150 6.0 140 C (8) 129.52 B (s) 132.42 5.5 130 D (s) 12074 5.0 120 4.5 f1 (ppm) ¹H NMR (500 MHz, Chloroform-d): 67.34 (d, J = 8.2 Hz, 1H), 6.87 (d, J = 8.2 Hz, 1H), 1.22 (s, 4.5H) 110 100 f1 (ppm) 4.0 90 How many carbons in this molecule? How many protons are in this molecule? 3.5 80 1 E (s) 77.99 3.0 70 2.5 60 2.0 50 1.5 40 車 10,12 F(s) 28 50 30 1.0 1 2 0.5 F0.3 0.2 -0.0 0.5 -0.4 -0.3 0.2 -0.1 13C NMR (125 MHz, Chloroform-d): 156.1, 132.4, 129.5, 120.7, 78.0, 28.5 MS: 184.07 m/z (100.0%), 186.06 m/z (32.0%), 185.07 m/z (11.0%), 187.07 m/z (3.5%) 0.0 What is the molecular formula and degree of unsaturation for this compound?
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