Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 19, Problem 19.53SP
A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. The barrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample, which she takes to her laboratory for analysis.
The mass spectrum shows a molecular ion at m/z 101, and the most abundant fragment is at m/z 86. The IR spectrum shows no absorptions above 3000cm−1, many absorptions between 2800 and 3000cm−1, no absorptions between 1500 and 2800cm−1, and a strong absorption at 1200cm−1. The proton NMR spectrum shows a triplet (J=7Hz) at δ1.0 and a quartet (J=7Hz) at δ2.4, with integrals of 17 spaces and 11 spaces, respectively.
- a. Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.
- b. Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers. Propose an inexpensive method for converting this waste to a solid, relatively odorless form for reburial.
- c. Suggest how the chemist can remove the fishy smell from her clothing.
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A compound A of mass 114 has the following elemental analysis: C = 63.14%, H=8.83%.
The IR, 1H NMR and 13C NMR spectra are given below.
1) Assign and interpret all the data from the 1H NMR and 13C NMR spectra. Propose a formula
for A.
7.0
175
с
3000
1,3; 13
I=1
6.0
150
I=1
с
5.0
CH₂
125
2000
Explain why the answer is this one :
CH,—CH,—0
4,2; 60
mavermy
I=2
cm-1
4.0
100
1500
3.0
75
135
167 |
CH₂
6
125
CH 3
1,95 ; 18
I=3
1000
2.0
50
H
5,5
I=3
1.0
CH₂
CH₂
25
500
Ppm
ppm
The infrared spectrum of a compound has a strong absorption at 1669 cm. The mass spectrum of
the compound is provided below. What is the structure of the compound?
100 -
80 -
60
40
20
0-
50
75
100
125
m/z
OH
NH2
Relative Intensity
A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. Thebarrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample,which she takes to her laboratory for analysis.The mass spectrum shows a molecular ion at m>z 101, and the most abundant fragment is at m>z 86. The IR spectrum shows no absorptions above 3000 cm-1, many absorptions between 2800 and 3000 cm-1, no absorptions between1500 and 2800 cm-1, and a strong absorption at 1200 cm-1. The proton NMR spectrum shows a triplet (J = 7 Hz) at d1.0and a quartet (J = 7 Hz) at d2.4, with integrals of 17 spaces and 11 spaces, respectively.(a) Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.(b) Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers.Propose an inexpensive method for converting this…
Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
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