Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 12.SE, Problem 20AP
The hormone cortisone contains C, H, and O, and shows a molecular ion at M+=360.1937 by high-resolution mass spectrometry. What is the molecular formula of cortisone? (The degree of unsaturation for cortisone is 8.)
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Chapter 12 Solutions
Organic Chemistry
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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- 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 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 (a) and the infrared spectrum (b) of an unknown hydrocarbon are shown. Propose as many structures as you can.arrow_forwardWhat is the most likely m/z value for the base peak in the mass spectrum of 3-methylpentane?arrow_forward
- Account for the formation of the base peak in these mass spectra. ( Q.) Isobutylamine, m/z 30arrow_forward2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?arrow_forwardPropose a molecular formula for a compound that exhibits the following peaks in its mass spectrum. (M)+• at m/z = 68, relative height = 100% (base peak) (M+1)+• at m/z = 69, relative height = 4.3%arrow_forward
- Propose structures for compounds that fit the following mass-spectral data: (a) A hydrocarbon with M+=132 (b) A hydrocarbon with M+=166 (c) A hydrocarbon with M+=84arrow_forwardCamphor, a saturated monoketone from the Asian camphor tree, is used among other things as a moth repellent and as a constituent of embalming fluid. If camphor has M+=152.1201 by high-resolution mass spectrometry, what is its molecular formula? How many rings does camphor have?arrow_forwardCarvone is an unsaturated ketone responsible for the odor of spearmint. If carvone has M+=150 in its mass spectrum and contains three double bonds and one ring, what is its molecular formula?arrow_forward
- When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3) shows a single sharp absorption at 7.3 δ. (a) How many parts per million downfield from TMS does chloroform absorb? (b) How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz? (c) What would be the position of the chloroform absorption in δ units when measured on a 360 MHz spectrometer?arrow_forwardThe mass spectrum of compound A shows the molecular ion at m/z 85, an M + 1 peak at m/z 86 of approximately 6% abundance relative to M, and an M + 2 peak at m/z 87 of less than 0.1% abundance relative to M. Q.) Draw at least ten possible structural formulas for this molecular formula.arrow_forward
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