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
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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- Determine the structure of the compound with the following spectral data. You must show your reasoning for full credit. (8pts) You must show your reasoning. MS: M+ (164) and M++2 in 1:1 ratio 1H-NMR: 3.5 (2H, triplet) 1.65 (2H, triplet) 0.9 (9H, singlet)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_forwardThe mass spectrum of the following compound shows fragments at m/z= 127, 113, and 85. Propose structures for the ions that give rise to thesepeaks.arrow_forward
- Compound 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_forward3. Propose a structure for a compound with the chemical formula C₂H4O that shows one peak in its 1H-NMR spectrum.arrow_forwardCompound E (C,H,0,) is a neutral solid. Its mass spectrum shows a molecular ion at mlz 138 and prominent peaks at M-1 and M - 17. Following are IR and 'H-NMR spectra of compound E. Deduce the structure of compound E. Micrometers 14 15 2.5 100 8 10 12 13 20 90 80 70 60 50 40 30 20 10 Compound E 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Wavenumber (cm-1) Transmittance (%)arrow_forward
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