Michael Addition Reaction Quiz

1,6-addition = Favored in many syntheses with specific substrate features Enantioselectivity = Influenced by catalysts in 1,6-addition reactions Michael addition = Used as a mechanistic step in covalent inhibitor drugs Polymerization reactions = Consist of initiation, propagation, and termination steps

Product 2 = 0% yield Product 3 = Mostly regioselective and enantioselective Product 4 = Less than 2% yield

Poly(amido amine) = Linear step growth polymerization product Poly(enamine ketone) = Result of using a wide variety of Michael donors and acceptors Poly(amino quinone) = Produces redox active coatings on metal surfaces Network polymers = Utilized for drug delivery, high performance composites, and coatings

<p>Initiation step = Involves the Michael addition of the nucleophile to a monomer Propagation step = Incorporates another monomer as an acceptor, extending the chain Termination step = Quenches the reaction by chain termination Michael donor = Can be a neutral donor or alkyl ligands bound to a metal</p> Signup and view all the answers

<p>Water = Participates as a non-carbon nucleophile in Michael addition Amines = Participates as a non-carbon nucleophile in Michael addition Doubly stabilized carbon nucleophiles = Participates as nucleophiles in Michael addition Enamines = Participates as a nucleophile in Michael addition</p> Signup and view all the answers

<p>Oxa-Michael reaction = Refers to the 1,4-addition of oxygen nucleophiles in Michael addition Aza-Michael reaction = Refers to the 1,4-addition of nitrogen nucleophiles in Michael addition 1,6-Michael reaction = Associated with 1,6-addition reactions in Michael addition Classical Michael reaction = Refers to the formation of carbon–carbon bonds through the addition of carbon nucleophiles</p> Signup and view all the answers

<p>Deprotonation of a nucleophile by a base = Leads to the formation of carbanion in the mechanism of the Michael addition reaction Formation of carbanion = Occurs in the mechanism of the Michael addition reaction Reaction via an enol or enolate nucleophile = Occurs in the mechanism of the Michael addition reaction Catalytic in base and irreversible at low temperature = Describes the mechanism of the Michael addition reaction</p> Signup and view all the answers

<p>Arthur Michael = Conducted research on the Michael reaction in 1887 Conrad &amp; Kuthzeit = Prompted Arthur Michael's research on the Michael reaction in 1884 Rainer Ludwig Claisen = Claimed priority for the invention of the Michael reaction Researchers who expanded the scope of Michael additions to include elements of chirality = Developed asymmetric versions of the Michael reaction</p> Signup and view all the answers

<p>Diethyl malonate and diethyl fumarate = Classical examples of the Michael reaction Diethyl malonate and mesityl oxide = Classical examples of the Michael reaction 2-nitropropane and methyl acrylate = Classical examples of the Michael reaction Synthesis of warfarin from 4-hydroxycoumarin and benzylideneacetone = Well-known example of the Michael reaction</p> Signup and view all the answers

<p>Mukaiyama–Michael addition = Involves a silyl enol ether as the nucleophile 1,6-Michael reaction = Proceeds via nucleophilic attack on the $\delta$ carbon of an $\alpha,\beta-\delta$-diunsaturated Michael acceptor Organocatalysis = Often favors the 1,4-addition in the Michael reaction Asymmetric versions of the Michael reaction = Involve the use of chiral phase transfer catalysis or organocatalysis</p> Signup and view all the answers

<p>Michael donor = Nucleophile that reacts with a Michael acceptor to form a Michael adduct Michael acceptor = Compound, usually α,β-unsaturated carbonyl, that reacts with a Michael donor to form a Michael adduct Enolate = Anion formed by deprotonation of a carbonyl compound Enantioselective = Describing a reaction that produces a single enantiomer of a chiral product</p> Signup and view all the answers

<p>Acyl, cyano, nitro, or sulfone groups = Electron-withdrawing groups on the Michael donor that make the adjacent methylene hydrogen acidic enough to form a carbanion Carbonyl group = R&quot; substituent on the Michael acceptor, usually α,β-unsaturated carbonyl compound Enolate = Nucleophile that can act as the Michael donor in the reaction Electron withdrawing group = R&quot; substituent on the Michael acceptor that can facilitate the Michael addition reaction</p> Signup and view all the answers

<p>The Michael reaction is an important method for diastereoselective and enantioselective C–C bond formation = Accurate statement regarding the significance of the Michael reaction The current definition of the Michael reaction has narrowed to include only enolates as nucleophiles = Inaccurate statement regarding the current definition of the Michael reaction The Michael addition is widely used for the mild formation of carbon-carbon bonds = Accurate statement regarding the utility of the Michael addition reaction The Michael reaction does not belong to the larger class of conjugate additions = Inaccurate statement regarding the classification of the Michael reaction</p> Signup and view all the answers

<p>Arthur Michael = Originally defined the Michael reaction as the addition of an enolate of a ketone or aldehyde to an α,β-unsaturated carbonyl compound at the β carbon Conjugate additions = Larger class to which the Michael addition belongs Asymmetric variants = Exist for the Michael addition to achieve enantioselective C–C bond formation Atom-economical method = Description of the Michael addition as a way to form carbon-carbon bonds</p> Signup and view all the answers

<p>1,6-addition product 2 = 0% yield 1,6-addition product 3 = approximately 99% yield 1,4-addition product 4 = less than 2% yield 1,6-Michael addition of ethyl sorbate 1 to product 3 = mostly regioselective and enantioselective</p> Signup and view all the answers

<p>Ibrutinib, osimertinib, and rociletinib = Contain an acrylamide functional group as a Michael acceptor Target enzyme inhibition = Following the Michael reaction Covalent inhibitor drugs = Using a Michael reaction as a mechanistic step Cancer treatment = Viable due to the target enzyme inhibition following the Michael reaction</p> Signup and view all the answers

<p>Poly(amido amine) = Linear step growth polymerization Poly(amino quinone) = Redox active polymer for anti-corrosion coatings Poly(aspartamide) = Linear step growth polymerization Network polymers = Used for drug delivery, high performance composites, and coatings</p> Signup and view all the answers

<p>Amines, thiols, and alkoxides = Neutral donors as Michael donors Alkyl ligands bound to a metal = Acting as a neutral donor for the Michael addition</p> Signup and view all the answers

<p>Michael donor = Provides the nucleophile for the reaction Michael acceptor = Receives the nucleophile to form a new carbon-carbon bond Enolate = A type of Michael donor, providing the nucleophilic carbon α,β-unsaturated carbonyl = A type of Michael acceptor, containing the electrophilic carbon for nucleophilic attack</p> Signup and view all the answers

<p>Acyl group = Electron-withdrawing substituent on the Michael donor, making the adjacent methylene hydrogen acidic Enone = A type of α,β-unsaturated carbonyl compound, commonly used as a Michael acceptor Nitro group = Electron-withdrawing substituent on the Michael donor, making the adjacent methylene hydrogen acidic Sulfone group = Electron-withdrawing substituent on the Michael donor, making the adjacent methylene hydrogen acidic</p> Signup and view all the answers

<p>Formation of carbanion = Involves the deprotonation of the methylene hydrogen on the Michael donor Nucleophilic attack = Involves the attack of the nucleophile on the electrophilic carbon of the Michael acceptor Carbon-carbon bond formation = Occurs between the nucleophile and the electrophile in the Michael addition reaction Enantioselective C–C bond formation = A key aspect of the Michael addition reaction, allowing for stereocontrol</p> Signup and view all the answers

<p>Conjugate addition = A larger class of reactions to which the Michael addition belongs Diastereoselective = Describes the selectivity of the Michael addition reaction towards diastereomers Asymmetric variants = Different versions of the Michael addition that favor the formation of one enantiomer over the other Atom-economical method = Refers to the efficiency of the Michael addition in forming carbon-carbon bonds</p> Signup and view all the answers

<p>Water = Nucleophile in Michael addition Alcohols = Nucleophile in Michael addition Amines = Nucleophile in Michael addition Enamines = Nucleophile in Michael addition</p> Signup and view all the answers

<p>Oxa-Michael reaction = Involves 1,4-addition of oxygen nucleophiles Aza-Michael reaction = Involves 1,4-addition of nitrogen nucleophiles 1,6-Michael reaction = Proceeds via nucleophilic attack on the 𝛿 carbon of an α,β- 𝛿-diunsaturated Michael acceptor Mukaiyama–Michael addition = Involves a silyl enol ether as the nucleophile and titanium tetrachloride as the catalyst</p> Signup and view all the answers

<p>Arthur Michael = Conducted research on the Michael reaction in 1887 Conrad &amp; Kuthzeit = Prompted Arthur Michael's research in 1884 Rainer Ludwig Claisen = Claimed priority for the invention of the Michael reaction Chiral phase transfer catalysis = Expanded the scope of Michael additions to include elements of chirality</p> Signup and view all the answers

<p>Diethyl malonate and diethyl fumarate = Classical example of the Michael reaction Diethyl malonate and mesityl oxide = Classical example of the Michael reaction 2-nitropropane and methyl acrylate = Classical example of the Michael reaction Warfarin synthesis = Well-known example of the Michael reaction</p> Signup and view all the answers

<p>Deprotonation of a nucleophile by a base = Leads to the formation of carbanion in the reaction mechanism Formation of carbanion = Occurs in the reaction mechanism of the Michael addition Reaction via an enol or enolate nucleophile = Part of the mechanism in the Michael addition Catalytic in base and irreversible at low temperature = Describes the reaction in the mechanism of the Michael addition</p> Signup and view all the answers

<p>Doubly stabilized carbon nucleophiles = Nucleophiles in Michael addition Non-carbon nucleophiles = Includes water, alcohols, amines, and enamines in the Michael addition Base = Deprontates a nucleophile in the reaction mechanism Electrophilic alkene = Reacts with carbanion to form product in the Michael addition</p> Signup and view all the answers