ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 23, Problem 22P
Interpretation Introduction
Interpretation:
The structures from F to I have to be determined with given information.
Concept Introduction:
>It is synthesized in plants as a toxin to other species for its protection.
>The organofluorine compounds are generally biosynthesized from the compound, fluoroacetaldehyde. Furthermore, it can also be artificially synthesized form 1-Bromo-8-fluoroocatane.
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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 23 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 23 - Prob. 1PPCh. 23 - Prob. 2PPCh. 23 - Prob. 3PPCh. 23 - Prob. 4PPCh. 23 - Prob. 5PPCh. 23 - Prob. 6PPCh. 23 - Prob. 7PPCh. 23 - Prob. 8PPCh. 23 - Prob. 9PPCh. 23 - Prob. 10PP
Ch. 23 - Prob. 11PPCh. 23 - Prob. 12PPCh. 23 - Prob. 13PPCh. 23 - Prob. 14PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - When limonene (Section 23.3) is heated strongly,...Ch. 23 - Gadoleic acid (C20H38O2), a fatty acid that can be...Ch. 23 - 23.20 -Phellandrene and -phellandrene are isomeric...Ch. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Prob. 27PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGP
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