Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.43P
Following is an equation for iodination of toluene.
This reaction does not take place. All that happens under experimental conditions for the formation of radicals is initiation to form iodine radicals, I , followed by termination to reform I2. How do you account for these observations?
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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 21 Solutions
Organic Chemistry
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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