The 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 B-keto ester, an enamine, or a B-diketone)and an a,B-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative.The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the stepsof this reaction follows.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsX UUOHHOPreviousNextSubmit AnawerRatry Entire Group9 more group attempts remainingEmail InstructorSave and E The 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 B-keto ester, an enamine, or a B-diketone)and an a,8-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative.The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the stepsof this reaction follows.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsH-AAOHHONestEmal InstructorSave and Ex

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The 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 B-keto ester, an enamine, or a B-diketone) and an a,8-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the steps of this reaction follows. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-A A OH HO

The 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 B-keto ester, an enamine, or a B-diketone) and an a,8-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the steps of this reaction follows. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-A A OH HO

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.9P

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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

The 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 B-keto ester, an enamine, or a B-diketone)
and an a,B-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative.
The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the steps
of this reaction follows.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
X UU
OH
HO
Previous
Next
Submit Anawer
Ratry Entire Group
9 more group attempts remaining
Email Instructor
Save and E

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The 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,
The 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:
The 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 ß-diketone) and an a,ß-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. il The above reaction between a ß-keto ester and an a,ß-unsaturated ketone yields a product containing a 2- cyclohexenone ring. One of the steps of this reaction follows. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AC↔XT я OEt -I H OEt CO₂Et Eto: يز OEt EtOH
base 2 H3C H H3C OH heat H H3C + H₂O H 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. 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 X :OH H₂O: а کی H₂C H H₂C H H
I 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 + H₂O
Provide a chemical reaction on how the following compounds can be synthesized via aldol condensation. note that the starting reactants should be benzaldehyde and a ketone
Please showcase whether its a full electron pair being moved or a singular electron moving
An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzed aldol addition of propanal.
Provide the reaction mechanism.
single reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?
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
Which step in the mechanism of the Aldol condensation reaction of a ketone is the one that makes the reaction irreversible? O Step 2 - attack of the nucleophilic enolate on a second equivalent of ketone to form a tetrahedral intermediate O Step 3 - protonation of the oxygen in the tetrahedral intermediate to form a beta- hydroxyketone O Step 5 - loss of hydroxide through an E1cb elimination O Step 1 - deprotonation of the ketone to form the enolate O Step 4 - deprotonation of the beta-hydroxyketone to form another enolate