EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 20, Problem 20.40P
Interpretation Introduction
Interpretation:
N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.
Concept introduction:
The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.
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Students have asked these similar questions
Why doesn't this carry on to form a ring by deprotonating the alpha carbon and the negatively-charged carbon attacking the C=O?
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
Ch. 20 - Prob. 20.1PCh. 20 - Prob. 20.2PCh. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Prob. 20.5PCh. 20 - Prob. 20.6PCh. 20 - Prob. 20.7PCh. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Prob. 20.28PCh. 20 - Prob. 20.29PCh. 20 - Prob. 20.30PCh. 20 - Prob. 20.31PCh. 20 - Prob. 20.32PCh. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Prob. 20.35PCh. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - Prob. 20.40PCh. 20 - Prob. 20.41PCh. 20 - Prob. 20.42PCh. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Prob. 20.45PCh. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - Prob. 20.51PCh. 20 - Prob. 20.52PCh. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - Prob. 20.57PCh. 20 - Prob. 20.58PCh. 20 - Prob. 20.59PCh. 20 - Prob. 20.60PCh. 20 - Prob. 20.61PCh. 20 - Prob. 20.62PCh. 20 - Prob. 20.63PCh. 20 - Prob. 20.64PCh. 20 - Prob. 20.65PCh. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - Prob. 20.69PCh. 20 - Prob. 20.70PCh. 20 - Prob. 20.71PCh. 20 - Prob. 20.1YTCh. 20 - Prob. 20.2YTCh. 20 - Prob. 20.3YTCh. 20 - Prob. 20.4YTCh. 20 - Prob. 20.5YTCh. 20 - Prob. 20.6YTCh. 20 - Prob. 20.7YTCh. 20 - Prob. 20.8YTCh. 20 - Prob. 20.9YTCh. 20 - Prob. 20.10YTCh. 20 - Prob. 20.11YTCh. 20 - Prob. 20.12YTCh. 20 - Prob. 20.13YT
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