Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 13, Problem 45P
For each of the following pairs of compounds, identify one IR absorption band that could be used to distinguish between them:
- a. CH3CH2CH2OH and CH3CH3OCH3
- b. cis-2-butene and trans-2-butene
- c. i CH3CH2CH=CHCH3 and CH3CH2C=CCH3
NOTE TO THE STUDENT
• There are additional spectroscopy problems in the Study Guide and Solution Manual.
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25. Match a structure from the list below to the following IR spectra. Place the letter of the structure in the
blank below the spectrum.
a. benzoic acid, C6H5COOH
b. methanol, CH3OH
c. benzaldehyde, C6H5CHO
d. phenol, C6H5OH
e. methyl acetate, CH3COOCH3
100
D
4100
LOD
50
HIT-NO-2237 |SCORE- (
Spectrum 1
D
3000
3347 B 1116 62
3336
1030
4
662
58
8
2946 18
2033 22
2622 77
2046 84
1460 47
|HIT-NO=1060 |SCORE= (
Spectrum 2
4000
1000
3229 4 2484 68
9048 15
3028 18
2962 29
2837 98
39
2725 41
2699 46
1933 57
1847 62
1711 64
1606 26
1598 10
1669 67
SOBS-NO-3302
m
1632 66
1501 14
3474 7
1372 23
43
1936
1315 47
1293 60
2008
SDBS-NO=554
HAVENUERI
p
2000
1234
15
1169 31
1153 25
1072 27
1024 49
889 41
881 60
826 36
812 23
754 8
691 6
617 44
IR-NIDA-63354 : LIQUID FILM
HAVENUISERI
555 18
602 20
1380
1000
IR-NIDA-29806 : LIQUID FILM
mummum
1500
300
1000
500
8. A strong signal in infrared spectroscopy indicates that a molecule matches the emitted
electromagnetic radiation and reports a high transmittance.
True
False
9. The signals observed from the C-C bond in an alkene will report at a higher wavenumber than
the C-C bond in an alkyne.
True
False
10. The electronegativity difference present in a dipole moment within a bond is directly
proportional to the electromagnetic field produced.
True
False
2. Which C4H,Br isomers give rise to the two spectra shown below?
b.
8
C.
8
7
7
6
5
5
34
4
8 (ppm)
33
32 PPM
4
8 (ppm)
2H
t
I
2H
d
3
ند
3
2H 2H
quint sext
NH
2
1H
m
2
6H
d
I
C
3H
1.0 PPM
0
0
Chapter 13 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 13.1 - Which of the following fragments produced in a...Ch. 13.2 - What distinguishes the mass spectrum of...Ch. 13.2 - What is the most likely m/z value for the base...Ch. 13.3 - Prob. 5PCh. 13.3 - a. Suggest possible molecular formulas for a...Ch. 13.3 - If a compound has a molecular ion with an...Ch. 13.3 - Identify the hydrocarbon that has a molecular ion...Ch. 13.4 - Predict the relative intensities of the molecular...Ch. 13.5 - Which molecular formula has an exact molecular...Ch. 13.5 - Prob. 11P
Ch. 13.6 - Sketch the mass spectrum expected for...Ch. 13.6 - The mass spectra of 1-methoxybutane,...Ch. 13.6 - Primary alcohols have a strong peak at m/z = 31....Ch. 13.6 - Identify the ketones responsible for the mass...Ch. 13.6 - Prob. 16PCh. 13.6 - Using curved arrows, show the principal fragments...Ch. 13.6 - The reaction of (Z)-2-pentene with water and a...Ch. 13.9 - a. Which is higher in energy: electromagnetic...Ch. 13.9 - Prob. 20PCh. 13.13 - Prob. 21PCh. 13.14 - Which occur at a larger wavenumber: a. the C O...Ch. 13.14 - Prob. 23PCh. 13.14 - Prob. 24PCh. 13.14 - Rank the following compounds from highest...Ch. 13.14 - Which shows an O H stretch at a larger...Ch. 13.16 - Prob. 27PCh. 13.16 - a. An oxygen-containing compound shows an...Ch. 13.16 - Prob. 29PCh. 13.16 - For each of the following pair of compounds, name...Ch. 13.17 - Which of the following compounds has a vibration...Ch. 13.17 - Prob. 32PCh. 13.18 - A compound with molecular formula C4H6O gives the...Ch. 13.20 - Prob. 34PCh. 13.20 - Prob. 35PCh. 13.21 - Predict the max of the following compound:Ch. 13.21 - Prob. 37PCh. 13.23 - a. At pH = 7 one of the ions shown here is purple...Ch. 13.23 - Prob. 39PCh. 13.23 - Prob. 40PCh. 13 - In the mass spectrum of the following compounds,...Ch. 13 - Prob. 42PCh. 13 - Draw structures for a saturated hydrocarbon that...Ch. 13 - Rank the following compounds in order of...Ch. 13 - For each of the following pairs of compounds,...Ch. 13 - a. How could you use IR spectroscopy to determine...Ch. 13 - Assuming that the force constant is approximately...Ch. 13 - Norlutin and Enovid are ketones that suppress so...Ch. 13 - In the following boxes, list the types of bonds...Ch. 13 - A mass spectrum shows significant peaks at m/z. =...Ch. 13 - Prob. 51PCh. 13 - Prob. 52PCh. 13 - Prob. 53PCh. 13 - The IR spectrum of a compound with molecular...Ch. 13 - Rank the following compounds from highest...Ch. 13 - Rank the following compounds from highest...Ch. 13 - What peaks in their mass spectra can be used to...Ch. 13 - Prob. 58PCh. 13 - Which one of the following five compounds produced...Ch. 13 - Prob. 60PCh. 13 - Each of the IR spectra shown below is accompanied...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - How can IR spectroscopy distinguish between...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Give approximate wavenumbers for the major...Ch. 13 - Prob. 68PCh. 13 - Which one of the following live compounds produced...Ch. 13 - Phenolphthalein is an acid-base indicator. In...Ch. 13 - Prob. 71PCh. 13 - How can you use UV spectroscopy to distinguish...Ch. 13 - Prob. 73PCh. 13 - The IR and mass spectra for three different...
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