ORGANIC CHEMISTRY (LL)-W/ACCESS
10th Edition
ISBN: 9781259717536
Author: Carey
Publisher: MCG
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Question
Chapter 21, Problem 41P
Interpretation Introduction
Interpretation:
The structure of product formed by the treatment of ethyl acetoacetate with the given reagents is to be drawn.
Concept introduction:
The replacement or substitution of one functional group with another different functional group in any
In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom.
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The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.
Suggest reasonable explanations for each of the following:
A. The rate of saponification of ethyl p-nitrobenzoate is 200 times faster than that of ethyl p-methoxybenzoate.
B. The rate of saponification of methyl acetate, CH3CCO2CH3 is 50 times greater than that for isopropylacetate.
The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?
Chapter 21 Solutions
ORGANIC CHEMISTRY (LL)-W/ACCESS
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
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