ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter H, Problem 5PP
Practice Problem H.5
Many alkaloids appear to be synthesized in plants by reactions that resemble the Mannich reaction (Section 19.8). Recognition of this (by R. Robinson in 1917) led to a synthesis of tropinone that takes place under “physiological conditions,” that is, at room temperature and at pH values near neutrality. This synthesis is shown here (and discussed in “Why These Topics Matter” at the end of Chapter 19). Propose reasonable mechanisms that account for the overall course of the reaction.
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a) Please draw a mechanism for the following reaction (you only have consider left to right). Identify the acid and
the base, the conjugate acid and the conjugate base.
OH
b) What direction would you expect the equilibrium to lie and by how much?
c) If an amine was added to above reaction, what would happen?
Q.6 Suggest a plausible mechanism for the following transformation
Ph
Ph
BuzSnH
AIBN
SMe
Do not use carboxylation mechanism but show full mechanism for the question below
Chapter H Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
Ch. H - Prob. 1PPCh. H - Prob. 2PPCh. H - Prob. 3PPCh. H - Practice Problem H.4
In 1891 G. Merling...Ch. H - Practice Problem H.5
Many alkaloids appear to be...Ch. H - Practice Problem H.6 Papaverine has been...Ch. H - Practice Problem H.7
One of the important steps in...Ch. H - Prob. 8PPCh. H - Practice Problem H.9 Gramine has been synthesized...
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