ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Chapter 13.SE, Problem 50AP
How could you use 1H NMR, 13C NMR, and IR spectroscopy to help you distinguish between the following structures?
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How would you use infrared spectroscopy to distinguish between the following pairs of constitutional isomers?
(a)
CH3C=CCH3
||
and
CH3CH2C=CH
(b)
CH3CCH=CHCH3
and
CH3CCH2CH=CH2
Problem 12-41
The mass spectrum (a) and the infrared spectrum (b) of an unknown hydrocarbon are shown. Propose as many
structures as you can.
(a)
100
Relative abundance (%)
80
60
60
40
200
20
(b)
100
Transmittance (%)
10
20
20
80-
60-
40-
20
40
60
80
100
120
140
m/z
500
4000 3500
3000
2500
2000
1500
Wavenumber (cm-1)
1000
Propagation of uncertainty. You have a stock solution certified by the manufacturer to contain 150.0±0.03 µg SO42-/mL. You would like to dilute it by a factor of 100 to obtain 1.500 µg/mL. Calculate the uncertainty in the two methods of dilution below. Use the following uncertainty values for glassware:
Glassware
Uncertainty
(assume glassware has been calibrated and treat the values below as random error)
1.00 mL volumetric pipet
0.01 mL
10.00 mL volumetric pipet
0.02 mL
100.00 mL volumetric flask
0.08 mL
Transfer 10.00 mL with a volumetric pipet and dilute it to 100 mL with a volumetric flask. Then take 10.00 mL of the resulting solution and dilute it a second time with a 100 mL flask.
2. Transfer 1.00 mL with a volumetric pipet and dilute it to 100 mL with a volumetric flask.
Draw all resonance structures for the following ion:
CH₂
Draw all resonance structures on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars, including
charges where needed. The single bond is active by default.
2D
ד
CONT
HD EXP CON
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1
[1]
Α
12
Marvin JS
by Chemaxon
A DOO
H
C
N
Br
I UZ OSPF
Chapter 13 Solutions
ORGANIC CHEMISTRY W/OWL
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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