Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 23.1, Problem 2P
Interpretation Introduction
Interpretation:
Using curved arrows to indicate the electron flow in each step, how the base catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone, is to be shown.
Concept introduction:
The steps involved in the retro-aldol reaction are i) Deprotonation by the base used ii) Elimination of the enolate ion iii) Protonation of the anion.
To show:
Using curved arrows to indicate the electron flow in each step how the base catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2‑Phenylacetaldehyde with benzaldehyde in the presence of sodium hydroxide undergoes a crossed aldol reaction.
An enolate attacks an aldehyde and the resulting product is subsequently protonated. What
type of reaction is this?
an acid-catalyzed aldol condensation
a Fischer esterification.
a Grignard reaction.
a base-mediated aldol condensation
Benzalacetone is a side product formed in the aldol condensation of dibenzalacetone. Show the reaction mechanism of how this side product, Benzalacetone, is formed.
Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
Knowledge Booster
Similar questions
- 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_forwardWhat is the mechanism for this Aldol reaction?arrow_forwardPlease assist in giving the mechanism of a Claisen Schmidt aldol reaction with 2-methylcyclohexanone and NaOH/EtOH as the base used.arrow_forward
- Define Intramolecular Aldol Reactions ?arrow_forwardThe first steps in the synthesis of azelnidipine, a calcium channel blocker, involves the reaction of β-keto ester A with aldehyde B in the presence of base. What crossed aldol product is formed in this reaction?arrow_forwardWrite the structure for each aldol condensation product that is possible when a mixture of ethanal and propanal is reacted with dilute NaOH.arrow_forward
- In theory, the intramolecular aldol reaction of 6-oxoheptanal could yield the three compounds shown. It turns out, though, that 1-acetylcyclopentene is by far the major product. Why are the other two compounds formed in only minor amounts? Draw a stepwise mechanism to show how all three products are formed.arrow_forward4) Provide the structure of the intramolecular aldol condensation/dehydration product(s) that results when diketone A below is heated in sodium hydroxide. A heptane-2,6-dionearrow_forwardShow how to prepare 5-hydroxy-4-methyl-3-hexanone using a crossed aldol reaction.arrow_forward
- An aldol condensation reaction using the reagents acetone and benzaldehyde, in the presence of sodium hydroxide was used to produce dibenzylacetone. Give a detailed NMR analysis for the product (address the issue of double bond stereochemistry; 3J values are sensitive to double bond geometry see diagram below).arrow_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 β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-keto ester and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product: Draw the β-keto ester as an ethyl ester,arrow_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 β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-diketone and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product:arrow_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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning