Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 22.4, Problem 22.7P

Without looking back, propose a mechanism for the hydrolysis of this iminium salt to the alkylated ketone The first step is attack by water, followed by loss of a proton to give a carbinolamine. Protonation on nitrogen allows pyrrolidine to leave, giving the protonated ketone.

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Chapter 22 Solutions

Organic Chemistry (9th Edition)

Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
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