Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 18, Problem 13PP
PRACTICE PROBLEM 18.13
The antiepileptic drug valproic acid is 2-propylpentanoic acid (administered as the sodium salt). One commercial synthesis of valproic acid begins with ethyl cyanoacetate. The penultimate step of this synthesis involves a decarboxylation, and the last step involves hydrolysis of a nitrile. Outline this synthesis.
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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 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
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