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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- Assume that you are in a laboratory carrying out the catalytic hydrogenation of cyclohexene to cyclohexane. How could you use a mass spectrometer to determine when the reaction is finished?arrow_forwardExplain the transitions occurring when acetaldehyde (H-CHO) is exposed to EM radiation. Also explain the two Amax obtained in its UV spectrum by giving out the corresponding spectrumarrow_forwardii) How are the spectroscopic techniques useful in the structural elucidation of following organic moleculesarrow_forward
- Q4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30arrow_forwardA sample of edible oil was subjected to analysis using mass spectrometry (MS). The following mass spectra (X and Y) were obtained. The spectra represent 2,4-decadienal and squalene. Identify the spectrum of 2,4-decadienal and squalene and explain your answer.arrow_forwardReduction of cyclohex-2-enone can yield cyclohexanone, cyclohex-2enol, or cyclohexanol, depending on the reagent and reaction conditions. How could you use IR spectroscopy to distinguish the three possible products?arrow_forward
- Saturated aldehyde Aromatic aldehyde At what position would you expect to observe IR absorption for the carbonyl groups in the following molecules? Infrared Absorptions of Some Aldehydes and Ketones. Carbonyl type Absorption cm-1 1730 1705 Example CH3CHO PhCHO a,ẞ-Unsaturated H2C=CHCHO 1705 aldehyde Saturated ketone CH3 COCH3 1715 Cyclohexanone 1715 Cyclopentanone 1750 Cyclobutanone Aromatic ketone 1785 PhCOCH3 a,ẞ-Unsaturated ketone H2C=CHCOCH3 1685 1690 Molecule #1: Molecule #2: CHO CHO CH3 cm-1 cm -1arrow_forward2. Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C₁2H17C1) and four dichlorinated products (C12H16C12). These products are easily separated by GC-MS, but the dechlorinated products are difficult to distinguish by their mass spectra. Draw the monochlorinated product and the four dichlorinated products, and explain how ¹3C NMR would easily distinguish among these compounds. (6 pts) Cl₂/hv Ch/v monochlorinated product dichlorinated products CIarrow_forward7 - Assign a structure to each of the following spectra. Choose from the following 5 carbon esters.arrow_forward
- How can you distinguish between aldehydes and ketones based on Infra-red spectroscopy?arrow_forwardIn the 1H NMR spectra of 2-bromopropane (CH3)2CHBr and 1-bromopropane CH3CH2CH2Br, how many signals do you expect to see?arrow_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
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