Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 18, Problem 52DSP
Interpretation Introduction
Interpretation:
The structures which are not the intermediates in the Baeyer-Villiger oxidation of cyclohexyl methyl ketone with peroxybenzoic acid are to be determined.
Concept Introduction:
During the Baeyer Villiger oxidation of
Usually, the oxygen atom is inserted between the carbonyl and the larger of the two groups attached to the carbonyl.
The ketone is converted to the conjugate acid of the ester.
The peroxy acid used is converted to the corresponding
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An esterification and a claisen condensation are the reverse of each other. Write a single equilibrium reaction that is appropriate for both reactions and discuss the experimental conditions that can drive this equilibrium toward one side or the other of this reaction.
The reactions are:
Esterification Reaction: acetic acid is reacted with methanol and sulfuric acid catalyst under heated conditions to produce methyl acetate.
Claisen Condensation: methyl acetate is reacted with water and sulfuric acid catalyst under heated conditions to produce acetic acid
What explains why many aldehydes and ketones can undergo self-condensation reactions in
basic conditions?
The alpha carbon can lose a proton and act like a nucleophile and the carbonyl
carbon is an electrophile.
The alpha carbon can gain a proton and act like an electrophile and the carbonyl
carbon is a nucleophile.
The oxygen of the carbonyl group can attack the carbon of the carbonyl group.
Only esters can undergo self-condensation reactions.
Hydration of aldehydes and ketones can be catalyzed by acid
or base. Bases catalyze hydration by:
protonating the carbonyl oxygen
making the carbonyl group more electrophilic
employing hydroxide ion, which is a better nucleophile than water
making the carbonyl group less electrophilic
shifting the equilibrium position of the reaction to favor products
Chapter 18 Solutions
Organic Chemistry - Standalone book
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.3 - Prob. 3PCh. 18.4 - Prob. 4PCh. 18.4 - Prob. 5PCh. 18.6 - Prob. 6PCh. 18.7 - Prob. 7PCh. 18.7 - Prob. 8PCh. 18.7 - Prob. 9PCh. 18.8 - Prob. 10P
Ch. 18.8 - Prob. 11PCh. 18.8 - Prob. 12PCh. 18.9 - Prob. 13PCh. 18.10 - Prob. 14PCh. 18.10 - Prob. 15PCh. 18.11 - Problem 18.16 The product of the following...Ch. 18.11 - Prob. 17PCh. 18.12 - Problem 18.18 What other combination of ylide and...Ch. 18.12 - Prob. 19PCh. 18.12 - Prob. 20PCh. 18.12 - Prob. 21PCh. 18.13 - Prob. 22PCh. 18 - (a) Write structural formulas and provide IUPAC...Ch. 18 - Each of the following aldehydes and ketones is...Ch. 18 - The African dwarf crocodile secretes a volatile...Ch. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Prob. 29PCh. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - Each of the following reaction has been reported...Ch. 18 - Prob. 33PCh. 18 - On standing in 17O-labeled water, both...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - The OH groups at C-4 and C-6 of methyl ...Ch. 18 - Prob. 38PCh. 18 - Prob. 39PCh. 18 - The sex attractant of the female winter moth has...Ch. 18 - Prob. 41PCh. 18 - Prob. 42PCh. 18 - Prob. 43PCh. 18 - Suggest a reasonable mechanism for each of the...Ch. 18 - Prob. 45PCh. 18 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Prob. 49PCh. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Prob. 52DSPCh. 18 - Prob. 53DSPCh. 18 - Prob. 54DSPCh. 18 - Prob. 55DSPCh. 18 - Prob. 56DSPCh. 18 - Prob. 57DSPCh. 18 - Prob. 58DSP
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