Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305780170
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 39AP
Carvone is an unsaturated
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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 to M.
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Chapter 12 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
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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- Camphor, 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_forwardThe mass spectra of two very stable cycloalkanes both show a molecular ion peak at m/z = 98 . One spectrum shows a base peak at m/z = 69, the other shows a base peak at m/z = 83. Identify the cycloalkane.arrow_forwardWhich compound gives rise to a major [M − 18] peak in the mass spectrum? Group of answer choices A. 1-bromoheptane B. 4-methylheptane C. 2-heptanol D. 3-ethylheptanearrow_forward
- Draw the structure of the important peaks in the mass spectrum of C9H8O (unsaturation = 6) Major Peaks: m/z = 132, 103, 77, 53arrow_forwardThe mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Determine the identity and structure of each of these fragmentsarrow_forwardThe following is the mass spectrum of a compound which contains one halogen atom. Which compound would you expect to give rise to the mass spectra shown below? A) Benzylbromide B) 3-Chloroperbenzoic acid C) Iodomethyl methyl ether D) 4-bromophenol E) 5-Chloro-2-nitroanilinearrow_forward
- 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 to M. Q.) Propose a molecular formula for compound A.arrow_forwardPropylbenzene, C6H5CH2CH2CH3, and isopropyl benzene, C6H5CH(CH3)2, are constitutional isomers with the molecular formula C9H12. One of these compounds shows prominent peaks in its mass spectrum at m/z 120 and 105. The other shows prominent peaks at m/z 120 and 91. Which compound has which spectrum?arrow_forwardA compound has a molecular ion in its mass spectrum at m / z = 58, and a strong absorption band at its IR at 1720. What would be the structure?arrow_forward
- 2,3-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_forwardCompound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2arrow_forwardA compound of unknown structure gave the following spectroscopic data: Mass spectrum: M+=88.1 IR: 3600 cm-1 1ΗNMR: 1.4 δ (2 H, quartet, J=7 Hz); 1.2 δ (6H, singlet): 1.0 δ (1 H, singlet); 0.9 δ (3 H, triplet, J=7 Hz) 13CNMR: 74, 35, 27, 25 δ (a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas (b) How many protons (H) does the compound contain? (c) What functional groups(s) does the compound contain? (d) How many carbons does the compound contain? (e) What is the molecular formula of the compound? (f) What is the structure of the compound? (g) Assign peaks in the molecule’s 1HNMR spectrum corresponding to specific protons.arrow_forward
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