ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Textbook Question
Chapter 12.SE, Problem 15AP
Write molecular formulas for compounds that show the following molecular ions in their high-resolution mass spectra, assuming that C, H, N, and O might be present. The exact
(a) M+=98.0844
(b) M+=123.0320
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In the mass spectrum of an unknown organic
compound, the molecular ion had a relative
abundance of 19.0 while the M+1 had a relative
abundance of 1.5.
Estimate the number of carbons in the molecule.
1
4
7
2
LO
5
8
carbons
3
6
9
X
C
14. Shown below are the mass spectra (without data tables) of four molecules. (The structure of each
molecule is shown on the spectrum.)
Mark the [M] peak for each, and indicate the molecular weight of the molecule.
Relative Intensity
Relative Intensity
100
80
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40-
20
0-mm
10
100-
80
a.
20-
115-14-5501
0-mm
10
20
b.
=0
20
30
30
40
40
50
50
60
m/z
60
m/z
70
70
80
80
90
100
90 100
Relative Intensity
Relative Intensity
100-
80
40
20
0
100
80
40
10
20-
15-NU-5580
15 20 25
115--555
ont
10
20
30
30
35 40 45 50 55
m/z
40
50
m/z
60
60
70
65 70 75
80
Based on the five mass spectra you have seen, describe how one might identify the [M]*
peak (molecular ion peak) on the mass spectrum of an unknown compound.
*(iii) The reaction of ethene with aqueous potassium manganate(VII), KMNO.,
produces ethane-1,2-diol, CH,OHCH,OH.
Data: molar mass of ethane-1,2-diol = 62 g mol
In an experiment, KMNO, containing only "O reacts with ethene.
Suggest how the mass spectrum of ethane-1,2-diol data could be used
to decide whether the oxygen atoms in ethane-1,2-diol came from the
manganate(VII) ion, water, or a combination of the two.
(2)
Chapter 12 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 12.2 - Prob. 1PCh. 12.2 - Two mass spectra are shown in FIGURE 12-8. One...Ch. 12.3 - What are the masses of the charged fragments...Ch. 12.3 - Prob. 4PCh. 12.5 - Prob. 5PCh. 12.5 - Prob. 6PCh. 12.7 - What functional groups might the following...Ch. 12.7 - How might you use IR spectroscopy to distinguish...Ch. 12.8 - Prob. 9PCh. 12.8 - Where might the following compounds have IR...
Ch. 12.8 - Where might the following compound have IR...Ch. 12.SE - Prob. 12VCCh. 12.SE - Show the structures of the fragments you would...Ch. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - Write molecular formulas for compounds that show...Ch. 12.SE - Camphor, a saturated monoketone from the Asian...Ch. 12.SE - The nitrogen rule of mass spectrometry says that a...Ch. 12.SE - In light of the nitrogen rule mentioned in Problem...Ch. 12.SE - Nicotine is a diamino compound isolated from dried...Ch. 12.SE - The hormone cortisone contains C, H, and O, and...Ch. 12.SE - Halogenated compounds are particularly easy to...Ch. 12.SE - Prob. 22APCh. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - 2-Methylpentane (C6H14) has the mass spectrum...Ch. 12.SE - Assume that you are in a laboratory carrying out...Ch. 12.SE - What fragments might you expect in the mass...Ch. 12.SE - How might you use IR spectroscopy to distinguish...Ch. 12.SE - Would you expect two enantiomers such as...Ch. 12.SE - Would you expect two diastereomers such as meso-2,...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - How could you use infrared spectroscopy to...Ch. 12.SE - Prob. 32APCh. 12.SE - At what approximate positions might the following...Ch. 12.SE - How would you use infrared spectroscopy to...Ch. 12.SE - At what approximate positions might the following...Ch. 12.SE - Assume that you are carrying out the dehydration...Ch. 12.SE - Assume that you are carrying out the base-induced...Ch. 12.SE - Prob. 38APCh. 12.SE - Carvone is an unsaturated ketone responsible for...Ch. 12.SE - Prob. 40APCh. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - 4-Methyl-2-pentanone and 3-methylpentanal are...Ch. 12.SE - Grignard reagents undergo a general and very...Ch. 12.SE - Ketones undergo a reduction when treated with...Ch. 12.SE - Nitriles, R–=C≡N, undergo a hydrolysis...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - Prob. 50AP
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