Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 37AP
Assume that you are carrying out the base-induced dehydrobromination of 3-bromo-3-methylpentane (Section 11-7) to yield an
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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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- Can someone go step by step on how to predict the masses and structure of the most abundant fragments of the 3-methylhex-2-ene mass spectra?arrow_forwardAssign the chemical shifts δ 1.1, δ 1.7, δ 2.0, and δ 2.3 to the appropriate protons of 2-pentanone.arrow_forwardWhat is the difference between absorption frequencies (infrared spectroscopy) for 2,3-dimethylbut-1-ene and 2,3-dimethylbut-2-ene? Why is it that the first structure has moderate intensity for the C=C bond while the second structure has weak/non-existent intensity for the "same" C=C bond?arrow_forward
- Could someone identify the proton splitting for 3-methylcyclohexene on the 1H nmr spectrumarrow_forwardHow is the molar mass of 2-methyl-2-hexanol is different from the M+1 peak of the mass spectrum?arrow_forwardA graduate student was following a procedure to make 3-propylcyclohexa-1,4-diene. He overheated the product. He isolated the product, which gave the appropriate =C−H stretch in the IR, but the C=C stretch appeared around 1630 cm−1as opposed to the literature value of 1650 cm−1for the desired product. The mass spectrum showed the correct molecular weight, but the base peak was at M–29 rather than at M–43 as expected. Because of the anomalous IR spectrum, he took a UV spectrum that showed λmaxat 261 nm. c) Draw the structure of the desired product and propose a structure for the actual product d) Show why he expected the MS base peak to be at M–43, and show how your proposed structure would give an intense peak at M–2arrow_forward
- When the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-Methylcyclohexanolarrow_forwardFollowing are infrared spectra of 2-methyl-1-butanol and tert-butyl methyl ether. Assign each compound its correct spectrum.arrow_forwardExplain all splitting patterns observed for absorptions between 0 and 8 ppm for the alcohol shown below. Which proton or protons will give rise to a doublet at 1.4 , which ones will give rise to a singlet at 2.7, which ones will give rise to a quartet at 4.7 and which ones will give rise to multiplets at 7.4?arrow_forward
- Fully interpret and compare the 13C NMR spectrum and the 1H NMR spectrum of the compound (R,R)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine. Label and explain the peaks and why they show up where they do.arrow_forward20. Clearly show how you would follow the oxidation of 1-propanol to propanoic acid by IR Spectroscopy. Which IR signals would disappear and which IR signals would appear as you go from reactant to product? Give the relative strength of the signals and approximate wavelength range of the signals. CH3CH2CH2OH --------> CH3CH2 C(O)OHarrow_forwardHow would you interpret this IR spectroscopy of 9-fluorenone? Some background information is that this was a lab to separate fluorene and 9-fluorenone. It should be noted that other solids and solvents used during the column chromatography was alumina, sand, petroleum ether, and dichloromethane. The original compound was 0.05 g but it yielded 0.03 g 9-fluorenone. There may or may not be impurities.arrow_forward
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY