Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 12.2, Problem 2P
Two mass spectra are shown in FIGURE 12-8. One spectrum is that of 2-methyl-2-pentene; the other is of 2-hexene. Which is which? Explain.
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Absorption and emission of electronic energy:
a) You find two bottles in the lab that have lost their labels. You know that the two
compounds are 2,3-dimethyl-1,3-butadiene and 2,5-dimethyl-1,3,5-hexatriene. You
find that UV absorbance maxima are at 226 nm and 252 nm. Which spectrum belongs
to which compound? How do you know this?
H.
H
Segment of
a sheet of
graphite
CH3
CH3
H
b) The (n to *) transition of N=0 has a maximum at 660 nm, while the ( to *) transition in C=C is at 180 nm.
Why would the transition for the N=O molecule be at a much longer wavelength? You may wish to use simple
HOMO and LUMO energy diagrams for clarity.
CH₂
c) Diamond and graphite are allotropic forms of carbon. Consider the molecular structures shown and the types
of bonds. Use them to explain why graphite (LEFT) is black while diamonds (RIGHT) are colourless.
Segment of
a diamond
a. Draw and name all of the isomeric products obtainedfrom the monobromination of propane with Br2/light. If halogenation were a completely randomreaction and had an equal probability of occurring atany of the C—H bonds in a molecule, what percentage of each of these monobromo products would beexpected?b. Answer part (a) using 2-methylpropane as the starting material.
Provide the structures (line, expanded structural or condensed structural formulas) for boxes
1-17 (there is no 13).
1
2
CH;OH
CH;OH
H*
H*
hemiketal
ketal
3
OH
H.
H*
H*
hemiacetal
acetal
6.
OH
OH
H*
H*
hemiketal
ketal
CH;OH
(excess)
H2SO4
8
CH3OH
(excess)
H2SO4
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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