Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 23AP
Propose structures for compounds that fit the following data:
(a) A
(b) An alcohol with M+=88 and fragments at m/z=73, m/z=70, and m/z=59
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3.1
Propose structures for compounds that fit the following data:
a) A benzoic acid with M+ = 122 and fragments at m/z = 105, and m/z = 77
b) An aldehyde with M+ = 76 and a fragment at m/z = 44.
The low-resolution mass spectrum of an unknown analgesic X had a molecular ion of 151. Possible molecular formulas include C7H5NO3, C8H9NO2, and C10H17N. High-resolution mass spectrometry gave an exact mass of 151.0640. What is the molecular formula of X?
Which compound correlates to the following mass spectrum?
100
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Relative htensity
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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- The base peak appears at m/z 83 for one of the following compounds and at m/z 97 for the other two. Match the m/z values for the base peaks with the appropriate compounds. compound xx m/z (Choose one) 97 83 (Choose one) (Choose one) X Ś 8 E olo 18 Ararrow_forwardThe base peak appears at m/z 83 for one of the following compounds and at m/z 97 for the other two. Match the m/z values for the base peaks with the appropriate compounds. compound xx 97 83 97 m/z Xarrow_forwarda) b) Acidity of Alcohols, Phenols and Thiols Predicting Acidity Rank the following compounds in order of increasing acidity: 1 1 OH OH Rel. Intensity 100 80 60 40 20 OH 0.0 2 0.0 2 OH Alcohols and Ethers Interpreting a Mass Spectrum give a peak at m/z = 45? 20 O 3 40 3 Example: Propose a structure for the following alcohol using the mass spectrum below (NOTE: there is a very small peak at m/z = 88) unknown MASS SPECTRUM OH LOH m/z 4 3 60 Hints: This is an alcohol, it has a mass of 88 so first determine the formula, then draw the possible structures. Now, which structure will fragment to OH OH 80 4 100arrow_forward
- Propose a molecular formula for a compound that exhibits the following peaks in its mass spectrum A: (M)+• at m/z = 68, relative height = 100% (base peak); (M+1)+• at m/z = 69, relative height = 4.3% B. (M)+• at m/z = 54, relative height = 100% (base peak); (M+1)+• at m/z = 55, relative height = 4.6%arrow_forwardThe intensity of M+, M+1, and M+2 peak are 100.0, 6.8, 31.9. The compound contains carbons, hydrogens, and a heteroatom. What is the molecular formula of the compound? (use format CxHyZ, where Z is heteroatom) 100 MS-NW-549S 80 60 40 10 20 30 40 50 60 70 80 90 100 110 Relative Intensity 20arrow_forwardThe intensities of peaks at 69 m/z, 70 m/z, and 71 m/z are 1.2, 31.2, and 1.7, respectively. How many carbons does the compound have? 100 MS-N-1334 80- 40 20- 10 15 20 25 30 35 40 45 50 55 60 65 70 m/z Relative Intensityarrow_forward
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