OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 22.SE, Problem 49AP
Interpretation Introduction
Interpretation:
How to synthesize from the malonic ester the dialkylated intermediate required for the synthesis of aprobarbitol is to be shown. Further a mechanism for the reaction of the intermediate with urea to give aprobarbitol is to be proposed.
Concept introduction:
Removal of both the hydrogens of the active methylene group in malonic ester by treating with LDA and then treating the enolate ions with
The steps involved in the reaction of the dialkylated product with urea are i) Nucleophilic attack of nitrogen of urea on the carbonyl carbon of the dialkylated ester ii) Elimination of the ethanol iii) Another nucleophilic attack by second nitrogen of urea on the carbonyl of the other ester group iv) Elimination of another ethanol.
To state:
How to synthesize from the malonic ester the dialkylated intermediate required for the synthesis of aprobarbitol. Further to propose a mechanism for the reaction of the intermediate with urea to give aprobarbitol
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Chapter 22 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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