Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 24, Problem 24.59P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction is to be drawn.
Concept introduction: The Aldol condensation reaction that takes place within the same molecule in presence of strong base is known as intramolecular aldol reactions. This reaction takes place within the dicarbonyl compounds in which one carbonyl group forms the enolate that acts as a nucleophile and reacts with second carbonyl group which acts as electrophile.
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Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.
Why is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone?
A) The Grignard reagent will react with the acid and cannot react with the ketone.
B) The ketone will be protonated and will become unreactive.
C) The ketone will form an unreactive enol.
D) The Grignard reagent won't dissolve in aqueous solutions
Draw structures for the carbonyl electrophile and enolate nucleophile.
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 24 - Acid-catalyzed dehydration of hydroxy carbonyl...Ch. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Problem 24.8
Draw the products formed in the...Ch. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Problem 24.16
What ester is formed when each...Ch. 24 - What crossed Claisen product is formed from each...Ch. 24 - Prob. 24.17PCh. 24 -
Draw the products of each reaction.
a. b.
Ch. 24 - Problem 24.20
Two steps in a synthesis of the...Ch. 24 - Prob. 24.20PCh. 24 - Problem 24.22
Which of the following compounds can...Ch. 24 - What product is formed when each pair of compounds...Ch. 24 - Problem 24.24
What starting materials are needed...Ch. 24 - Problem 24.25
Draw the products when each pair of...Ch. 24 - Problem 24.27
What starting materials are needed...Ch. 24 - Prob. 24.26PCh. 24 - 24.29 What steps are needed to convert A to B?
Ch. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.31PCh. 24 - What starting materials are needed to synthesize...Ch. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Draw the product formed from a Claisen reaction...Ch. 24 - Prob. 24.41PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.43PCh. 24 - What starting materials are needed to prepare each...Ch. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.47PCh. 24 - Draw the organic products formed when butanal...Ch. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Devise a synthesis of each compound from...Ch. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75P
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