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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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
2 Moin H3C H H₂C C⇒x= base :0: OH Hori H3C 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 B-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 H₂C Ἡ :0: heat H Home H3C + H₂O
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
base H3C H OH heat H + 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. In the mixed aldol reaction, the best results are obtained when one of the partners does not have an a-hydrogen. It cannot form an enolate anion and can therefore not undergo self-reaction. The enolizable aldehyde is added slowly to a basic solution of the first aldehyde so that the mixed product is preferentially formed. 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.…
H₂C=CHCCH3 then H3O+ The Michael reaction is a conjugate addition process wherein a nucleophilic enolate anion (the donor) reacts with an a,ß-unsaturated carbonyl compound (the acceptor). The best Michael reactions are those that take place when a particularly stable enolate anion is formed via treatment of the donor with a strong base. Alternatively, milder conditions can be used if an enamine is chosen as the donor, this variant is termed the Stork reaction. In the second step, the donor adds to the ẞ-carbon of the acceptor in a conjugate addition, generating a new enolate. The enolate abstracts a proton from solvent or from a new donor molecule to give the conjugate addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions N 9a
The behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 2 O 4 O 1
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
Step 3: If excess alcohol is present in the hemiacetal, the hemiacetal can be further converted to an acetal product, but only in the presence of acid. R₁ R₂ R3OH, H+ HO OR3 R3OH, H+ R3Q OR 3 + H2O R₁ R₁ R₂ hemiacetal acetal Why is acid required? The alkoxy group in the hemiacetal must first be converted into a good leaving group. Acid stabilizes the product. Acid stabilizes the hemiacetal, making it more reactive. The hydroxy group in the hemiacetal must first be converted into a good leaving group.
Please give the appropriate reagents to complete the following synthesis. H ? hy=3