Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 21, Problem 43P
Interpretation Introduction
Interpretation:
The structure of the product that is formed if the given reactant undergoes intramolecular aldol condensation is to be explained.
Concept introduction:
Aldol condensation is a specific type of condensation reaction that is taken place only those carbonyl compounds that have alpha hydrogen with them.
In this reaction, first, there is the formation of an enol or an enolate ion that ultimately attacks the carbonyl group of another molecule to form a beta hydroxy
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.
The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of
formation of an enamine from a ketone,
Michael addition to an α,β-unsaturated carbonyl compound, and
hydrolysis of the enamine in dilute acid to regenerate the ketone.
Consider the Stork reaction between cyclohexanone and propenal
Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine.
- Michael addition to an α,β-unsaturated carbonyl compound, and
- hydrolysis of the enamine in dilute acid to regenerate the ketone.
The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of
formation of an enamine from a ketone,
Michael addition to an α,β-unsaturated carbonyl compound, and
hydrolysis of the enamine in dilute acid to regenerate the ketone.
Consider the Stork reaction between acetophenone and 3-buten-2-one.
Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine.
Draw the structure of the Michael addition product.
Draw the structure of the final product.
Chapter 21 Solutions
Organic Chemistry - Standalone book
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardThe compound 3,5,5-trimethyl-2-cyclohexenone can be synthesized using acetone and ethyl acetoacetate as sources of carbon atoms. New carbon-carbon bonds in this synthesis are formed by a combination of aldol reactions and Michael reactions. Show reagents and conditions by which this synthesis might be accomplished.arrow_forward
- 2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardWhat product is obtained when the following compound undergoes two successive elimination reactions?arrow_forward
- What is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction? What is the product obtained when product A reacted with ethyl acetate in the same basic solution?arrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0 °C, followed by treatment with N,N-diethylaniline.arrow_forwardPropose a mechanism for the acid-catalyzed reaction of cyclohexanone with ethylene glycol to give cyclohexanone ethylene acetal.arrow_forward
- Give the product of the following transformation:arrow_forwardI H H3C NOC XT :0: MET H₂C base H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. H OH q H3C H₂C H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions heat H H + H₂Oarrow_forwardThe Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a ß-keto ester, an enamine, or a 6-diketone) and an a 6-unsaturated ketone acceptor The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic B-diketone and the a B-unsaturated ketone acceptor that wvere combined in a Robinson annulation to give the following product: Ph C P 000- IFarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License