ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Textbook Question
Chapter 17.SE, Problem 52AP
Propose structures for alcohols that have the following 1HNMR spectra:
(a) C5H12O
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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
?
1
[1]
Α
12
Marvin JS
by Chemaxon
A DOO
H
C
N
Br
I UZ OSPF
Chapter 17 Solutions
ORGANIC CHEMISTRY W/OWL
Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2PCh. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5PCh. 17.3 - Prob. 6PCh. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8PCh. 17.5 - Prob. 9PCh. 17.5 - Prob. 10P
Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
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