Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 14, Problem 14.27P
Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)
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A mass peak at m/z = 59 appears in the mass spectrum of an amide, C5H11NO. Draw the structure of a molecule that is consistent with this result.
Following is the mass spectrum of an unknown compound. The two highest peaks are
at mlz 120 and 122. Suggest a structure for this compound. (Data from http://webbook
.nist.gov/chemistry/.)
100
41
80
20
120
122
0 rt
10
20
30
40
60
70
110
140
80
90
m/z
50
100
120
130
150
160
Relative Abundance
c) The mass spectrum of 2,3-dibromopentane (CH; CHBr CHBr CH₂ CH3) includes the following peaks.
Mass number (m/z) Relative abundance
15
29
107
109
199
201
203
i. What is the mass number of molecular ion, [CH; CHBr CHBr CH₂ CH₂]? Show your working.
ii. Identify the molecular formula (including isotopic composition where relevant) of the 6 peaks.
a
b
d
22
e
f
Mass number (m/z)
15
29
107
109
199
100
39
44
45
0.3
0.6
0.3
201
203
Molecule formula
[CH₂]
Chapter 14 Solutions
Organic Chemistry
Ch. 14.2 - Calculate the nominal mass of each ion. Unless...Ch. 14.3 - Propose a structural formula for the cation at m/z...Ch. 14.3 - The low-resolution mass spectrum of 2-pentanol...Ch. 14 - Draw acceptable Lewis structures for the molecular...Ch. 14 - The molecular ion for compounds containing only C,...Ch. 14 - For which compounds containing a heteroatom (an...Ch. 14 - The so-called nitrogen rule states that if a...Ch. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Determine the probability of the following in a...Ch. 14 - The molecular ions of both C5H10S and C6H14O...Ch. 14 - Prob. 14.13PCh. 14 - Carboxylic acids often give a strong fragment ion...Ch. 14 - For primary amines with no branching on the carbon...Ch. 14 - Prob. 14.16PCh. 14 - A characteristic peak in the mass spectrum of most...Ch. 14 - Predict the relative intensities of the M and M +...Ch. 14 - The mass spectrum of compound A shows the...Ch. 14 - The mass spectrum of compound B, a colorless...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - The molecular ion in the mass spectrum of...Ch. 14 - Prob. 14.24PCh. 14 - Following is the mass spectrum of 1-bromobutane....Ch. 14 - Following is the mass spectrum of...Ch. 14 - Following is the mass spectrum of an unknown...Ch. 14 - Following is the mass spectrum of...Ch. 14 - Prob. 14.29PCh. 14 - Following are mass spectra for the constitutional...Ch. 14 - 2-Methylpentanal and 4-methyl-2-pentanone are...Ch. 14 - Prob. 14.32PCh. 14 - Account for the presence of the following peaks in...Ch. 14 - All methyl esters of long-chain aliphatic acids...Ch. 14 - Propylbenzene, C6H5CH2CH2CH3, and isopropyl...Ch. 14 - Account for the formation of the base peaks in...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38P
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