Macroscale and Microscale Organic Experiments
7th Edition
ISBN: 9781337329552
Author: Kenneth L. Williamson; Katherine M. Masters
Publisher: Cengage Learning US
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Chapter 6, Problem 6Q
A mixture of toluene
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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed
a chemical structure shown below:
% Transmittance
4000
3500
3000
2500 2000
Wavenumber (cm-1)
1500
1000
(a) Explain why her proposed structure is inconsistent with the IR spectrum obtained
(b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure
and explain why it is more compatible with the obtained spectrum.
(C) what is the possible source for the fairly intense signal at
1621cm1
AE>AE₁ (Y/N)
AE=AE₁ (Y/N)
AE
Treatment of 2-phenylpropan-2-amine with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and
gives compound A.
?
NH2
Br
Br
Propose a structural formula for compound A.
You do not have to explicitly draw H atoms.
You do not have to consider stereochemistry.
In cases where there is more than one answer, just draw one.
R3N
C14H19NO2
+ 2 R3NH*Br
A
Chapter 6 Solutions
Macroscale and Microscale Organic Experiments
Ch. 6 - Assign the peaks in the 1H NMR spectrum of eugenol...Ch. 6 - A mixture of ethyl iodide (C2H5I,bp72.3C) and...Ch. 6 - Prob. 3QCh. 6 - Prob. 4QCh. 6 - Prob. 5QCh. 6 - A mixture of toluene (bp110.8C) and water is steam...Ch. 6 - Did sublimation aid in the purification of the...Ch. 6 - Prob. 8QCh. 6 - Prob. 9QCh. 6 - Prob. 10Q
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Solutions: Crash Course Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=9h2f1Bjr0p4;License: Standard YouTube License, CC-BY