Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 12, Problem 12.31SP
Consider the following four structures, followed by mass spectral data. Match each structure with its characteristic molecular ion or fragment. In each case, give a likely structure of the ion responsible for the base peak.
- a. base peak at 105
- b. base peak at 72
- c. M+ doublet at 198 and 200, base peak at 91
- d. base peak at 91, large peak at 43
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What would distinguish the mass spectrum of 2,2-dimethylpropane from those of 2-
methylbutane and n-pentane?
A. molecular ion peak at 72
B. base peak at 15
C. base peak at 27
D. base peak at 43
E. base peak at 57
B. MASS SPECTRUM
Identify the following from the low resolution mass spectrum of the unknown compound:
100
Relative intensity
LT.
80
80
60
40
20
Base peak
0
20
Molecular lon peak
40
Mass Spectrum of Compound
P
121
152
60
C. DOUBLE BOND EQUIVALENTS
Calculate the DBE of the unknown compound.
m/z
This information indicates, for example, the presence of
100
Mass spectrum of the compound.
120
140
160
a + x
On each mass spectrum above, indicate the base peak and the molecular ion peak (or at least where you would expect to find it) and if the base peak on the mass spectrum for linalool has m/z 71, propose a structure for this fragment ion.
Chapter 12 Solutions
Organic Chemistry (9th Edition)
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
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- 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/.)arrow_forwardWrite 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 atomic masses are: 1.007 83 (1H), 12.000 00 (12C), 14.003 07 (14N), 15.994 91 (16O). (a) M+=98.0844 (b) M+=123.0320arrow_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forward
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