Esters with only one α hydrogen generally give poor yields in the Claisen condensation.Q: Propose a mechanism for the Claisen condensation of ethyl isobutyrate. Esters with only one a hydrogen generally give poor yields in the Claisen condensation.Part APropose a mechanism for the Claisen condensation of ethyl isobutyrate.Draw all missing reactants, reagents, intermediates, and/or products inside the appropriate boxes by choosing buttons from the Tools (for bonds and charges), Atoms,and Templates toolbars.CONT.HC

It is an organic coupling reaction which results in formation of a carbon-carbon bond between either…

Answered: Claisen condensation of ethyl…

Science

Chemistry

Claisen condensation of ethyl isobutyrate.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 9E

See similar textbooks

Related questions

Q: Reaction benzaldehyde with (CH3CN) in presence of base called ? (a)Dopner reaction (b)Crossed…

Q: Use the malonic ester synthesis to prepare each carboxylic acid.

A: Melonic ester synthesis method is used to synthesise carboxylic acids with desired carbon chain.

Q: Use the retro synthesis to determine the diketone from which the following compounds were formed by…

A: In the intramolecular alodol condenstation reaction nucleophilic attack happen in the same molecule.

Q: CH3 нн エ -エ、エエ

A: As the given base is LDA i.e. Lithium diisopropylamide. It is a bulky base which favours the…

Q: Show all possible Claisen condensation products AND their hydrolysis and decarboxylation products.…

Q: The following molecule is formed in a mixed aldol condensation reaction. organic starting materials…

A: As we know , we get beta hydroxy ketone in the aldol condensation reaction. Also condensation is…

Q: Dehydration via an E1cb mechanism Michael Reaction Intramolecular Aldol Reaction В KOH / ELOH / heat…

A: We know, Micheal reaction is basically the nucleuphilic addition reaction which is basically 1-4…

Q: 2 CH3COOCH,CH3 C2H5O°K"/C2HSOH ---> CH3COCH2COOCH2CH3 +] Hofmann elimination Clemmensen reduction…

A: The above given reaction is a claisen condensation. Claisen condensation is a organic coupling…

Q: into the indicated products. Identify the substrate, reagent(s) and catalyst if any used for each…

Q: Show how to synthesize the following compound using either the malonic ester synthesis or the…

A: 4-Phenyl-2-butanone: Its common name is benzylacetone. It is flowery in smell. It is prepared by…

Q: Propose a retrosynthesis of the following compound using the michel reaction.

Q: Propose a mechanism, using curved arrows, for the base-catalysed aldol reaction and the subsequent…

Q: Dehydration via an E1cb mechanism Michael Reaction Intramolecular Aldol Reaction А C KOH / ETOH /…

Q: Match the following reagents with the use they have in their respective reactions. A good molecule…

A: Match the following

Q: Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro…

A: The given reaction is,

Q: What would be the best reagents to carry out the following Fischer esterification? OCH, methanamid…

A: The correct answer is given below

Q: Match the reactions with the correct description. Match each item to a choice: Acetoacetic ester…

Q: ArSO,H Draw curved arrows to show the movement of electrons in the following step of an…

Q: One step in a recent short synthesis of a prostaglandin involves the conversion of succinaldehyde to…

A: The mechanism is as follows,

Q: 1. What is name of the starting material for the reaction sequence shown in the box? CH3 NaOH, H20…

Q: 2. Illustrate detailed mechanisms for below attempted aldol reaction. CH3 CH' H. H. NAOH CH3

A: Aldol reaction involves the formation of an enolate ion in the presence of a strong base for which a…

Q: Show

A: We will write the mechanism of aldol

Q: Using cyclopentanone as the reactant, show the product of a. acid-catalyzed keto–enol…

A: The acid-catalyzed keto-enol interconvertion has to be given.

Q: Define Intramolecular Aldol Reactions ?

A: Mechanism and example of intramolecular aldol reaction

Q: Show how to prepare a,b-unsaturated ketone by an aldol reaction followed by dehydration of the…

A: The given product is,

Q: Propose a mechanism for conversion of the dianion to the ketone under mildly acidic conditions.

Q: OVERALL REACTION Michael reaction NaOCH, CH,OH H3CO OCH3 H,CO. OCH3 mesityl oxide dimethyl malonate…

A: The reaction taking place is given as,

Q: Propose a synthesis for each ketone, using as one step in the sequence a Claisen condensation and…

A: The given chemical reaction is, The sodium ethoxide would abstract an alpha hydrogen from the…

Q: ArSO,H Draw curved arrows to show the movement of electrons in the following step of an…

Q: What is the reaction mechanism? (Esterification) Please Explain also. Starting Materials:…

A: In the esterification reaction, the carboxylic acid reacts with alcohol in presence of an acid to…

Q: Propose a synthesis for each ketone, using as one step in the sequence a Claisen condensation and…

Q: Show how to synthesize the following compound using either the malonic ester synthesis or the…

A: The malonic ester synthesis of 2-Propyl-1,3-propanediol undergoes a nuclophilic attack using strong…

Q: Propose a mechanism for the aldol reaction below 2 H3C H OH-, H₂O H3C H

Q: Draw the product formed when each dicarbonyl compound undergoes anintramolecular aldol reaction…

Q: Pent-4-enoic acid may be synthesized from diethyl malonate in a few steps. Draw a reasonable…

A: Pent-4-enoic acid is synthesized from diethyl malonate. The reaction procedure that can be used to…

Q: Rank the following compounds toward increasing acidity as shown below CH3NO2 > CH3COCH3 > CH3COOCH3>…

A: Greater the stability of conjugate base higher is the acidicity

Q: 4-methyl,2-pentanol by aldol comdensation with mechanisam

A: Aldol condensation is a base catalyzed condensation reaction in which two molecules of carbonyl…

Q: Show the product of treating y-butyrolactone with reagent.

A: The product of gamma-butyrolactone with the given reagent should be shown.

Q: + 2 MetoH H2SO4 + HzO + C HO. A

A: Fischer esterification reaction is the formation of ester as a product with the reaction of…

Q: Identify the best reagents to complete the following reaction. H2O pyridine PHCH2OH pyridine PHOH…

Q: Cardiolipins are found in heart muscles. Draw the products formed when a cardiolipin undergoes…

A: The mechanism is as follows:

Q: Show the steps in preparing each of the following substances using either a malonic ester synthesis…

A: In the ball-stick representation for the structure of a compound, white ball represents H-atom, grey…

Q: In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of sodium…

A: Given: In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of…

Q: Which compound will decarboxylates the easiest when heated in aqueous acid?

A: Decarboxylation is a chemical reaction in which carcoxyl group is eliminated from the carbon chain…

Q: Draw both enolates formed when the ketone is treated with base. Include charges. Draw the oxyanion…

A: The organic compound which is formed after deprotonation of acidic proton from alpha carbon w.r.t…

Q: b. ) What starting compound would you use in an Aldol condensation in the following compound?…

Q: Complete the synthetic sequences by drawing products/substrates/reagents in empty spaces in…

A: Note: according to our guidelines we are supposed to answer only first three subparts. Kindly repost…

Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Esters with only one α hydrogen generally give poor yields in the Claisen condensation.

Q: Propose a mechanism for the Claisen condensation of ethyl isobutyrate.

Esters with only one a hydrogen generally give poor yields in the Claisen condensation.
Part A
Propose a mechanism for the Claisen condensation of ethyl isobutyrate.
Draw all missing reactants, reagents, intermediates, and/or products inside the appropriate boxes by choosing buttons from the Tools (for bonds and charges), Atoms,
and Templates toolbars.
CONT.
H
C

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

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

Answer the following question about curcumin, a yellow pigmentisolated from turmeric, a tropical perennial in the ginger family and aprincipal ingredient in curry powder. Most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols.
Do not give handwriting solution. please draw out what compound A is and then provide aroow pushing mechanism for thisreaction! thanks01 Cive the ctrientiono of Comnand 4 2.2 Provide a reasonable arrowpushing mechanism for the reaction in 2.1
Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.
2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasmine-like odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reaction between benzaldehyde (C6H5CHO) and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.
Which halide in the attached marine natural product reacts fastest inthe SN2 reaction?
The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below: a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed.b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole.
2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasminelike odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reactionbetween benzaldehyde (C6H5CHO) and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.
a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of thetetrahedral intermediate): b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of thetetrahedralintermediate).
Devise a synthesis of each compound using 1-bromobutane(CH3CH2CH2CH2Br) as the only organic starting material. You may useany other inorganic reagents.
This question has multiple parts. Work all the parts to get the most points. 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.
This question has multiple parts. Work all the parts to get the most points. 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 ethyl propenoate. Draw the structure of the product of the enamine formed between acetophenone and dimethylamine.
Identify the correct reagents with the correct letter for carrying out the following synthesis.