Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 25, Problem 25.30AP
Interpretation Introduction
Interpretation:
A curved arrow mechanism for the hydrolysis of trimethyl phosphate to dimethyl phosphate in acidic solution containing
Concept Introduction:
The hydrolysis of trimethyl phosphate produces methanol and dimethyl phosphate as the products. The sequence in which bond breaking takes place decides the product which will contain the labelled oxygen atom used in the reaction.
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Answer
2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton
transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted
without ambiguity.
a.
CH3
Ph
OEt
هد
Ph
CH3
Hint: the species on the left is an ynolate, which behaves a lot like an enolate.
b.
CH3
H3C
CH3
CH3
H3C
an unexpected product,
containing a single 9-
membered ring
the expected product,
containing two fused rings
H3C-I
(H3C)2CuLi
an enolate
Chapter 25 Solutions
Organic Chemistry
Ch. 25 - Prob. 25.1PCh. 25 - Prob. 25.2PCh. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21APCh. 25 - Prob. 25.22APCh. 25 - Prob. 25.23APCh. 25 - Prob. 25.24APCh. 25 - Prob. 25.25APCh. 25 - Prob. 25.26APCh. 25 - Prob. 25.27APCh. 25 - Prob. 25.28APCh. 25 - Prob. 25.29APCh. 25 - Prob. 25.30APCh. 25 - Prob. 25.31APCh. 25 - Prob. 25.32APCh. 25 - Prob. 25.33APCh. 25 - Prob. 25.34APCh. 25 - Prob. 25.35APCh. 25 - Prob. 25.36APCh. 25 - Prob. 25.37APCh. 25 - Prob. 25.38APCh. 25 - Prob. 25.39APCh. 25 - Prob. 25.40AP
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