Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 48AP
The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000 cm-1. There is a prominent peak near 1740 cm-1 and another strong peak near 1200 cm-1. Propose a structure consistent with the data.
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Chapter 12 Solutions
Organic Chemistry
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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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- A compound contains only C, H and O. The mass spectrum shows peaks at m/z = 58 and 43. What is the structure of the compound?arrow_forward[References] The 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 М. Assuming that compound A has only C, H, and one N atoms, determine the molecular formula, and then draw a possible structure if compound A has IR absorption at 1620-1680 cm1 but not at 3010-3090 cm-1 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. Separate structures with + signs from the drop-down menu. C opy aste ChemDoodle h 51% 10:53 A 3/23/202arrow_forwardCompound C shows a molecular ion at m/z 148 and other prominent peaks at m/z 105 and 77. Following are its infrared and 1H-NMR spectra. Q.) Account for the appearance of peaks in its mass spectrum at m/z 105 and 77.arrow_forward
- An unknown compound produces an 1H NMR spectrum with only three signals: 1.8, 2.8, 7.5 (broad) ppm, all singlets that integrate in a 6:3:1 ratio, respectively. The 13C NMR spectrum shows 4 signals. Both spectra are provided below. The mass spectrum shows a molecular ion region with the following peaks: m/z 135 (100%), 136 (5.9%), 137 (33%). Determine the number of carbons, molecular formula, and propose a structure. Assign all 1H and 13C NMR signals to specific chemical environments or specific hydrogens in your structure. 'H NMR Spectrum of Unknown 8 6 PPM 13C NMR Spectrum of Unknown 160 140 80 60 100 PPM 180 120 40 20arrow_forwardPredict the structure of the compound using the information below. Kindly show what information are obtained for each spectra which may help in predicting the structure. From IR Spectra: See the attached picture From Mass Spectra M+ = 87 From Proton and Carbon NMR Spectra See attached picture.arrow_forwardA mass spectrum has an M+ peak at 204 m/z; and additional peaks starting at 127, 77, along with some other smaller peaks. Which of the following reactions could have produced this compound? CH3CH2Cl & AlCl3 plus toluene KI plus a benzene diazonium ion Fuming sulfuric acid plus toluene, followed by dilute acid 2 CuCl plus a diazonium ion Benzonitrile plus LiAlH4 followed by fuming sulfuric acid Thank you!arrow_forward
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