28 Questions
Match the following terms with their descriptions:
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
Match the following products with their corresponding yields in the 1,6-addition reaction:
Product 2 = 0% yield Product 3 = Mostly regioselective and enantioselective Product 4 = Less than 2% yield
Match the following polymerization examples with their corresponding polymers:
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
Match the following terms with their roles in polymerization reactions:
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
Match the following nucleophiles with their involvement in the Michael addition reaction:
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
Match the following terms with their corresponding 1,4-addition reactions in Michael addition:
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
Match the following statements with their involvement in the mechanism of the Michael addition reaction:
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
Match the following researchers with their contributions to the Michael addition reaction:
Arthur Michael = Conducted research on the Michael reaction in 1887 Conrad & 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
Match the following examples with their association to the Michael reaction:
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
Match the following terms with their involvement in specific types of Michael addition reactions:
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
Match the following terms with their definitions in organic chemistry:
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
Match the following groups with their role in the Michael addition reaction:
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" 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" substituent on the Michael acceptor that can facilitate the Michael addition reaction
Match the following statements with their accuracy regarding the Michael reaction:
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
Match the following terms with their role in the Michael addition reaction:
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
Match the following Michael addition products with their corresponding yields:
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
Match the following pharmaceuticals with their role in cancer treatment:
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
Match the following polymerization examples with their corresponding polymers:
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
Match the following nucleophiles with their involvement in the Michael addition reaction:
Amines, thiols, and alkoxides = Neutral donors as Michael donors Alkyl ligands bound to a metal = Acting as a neutral donor for the Michael addition
Match the following terms with their role in the Michael addition reaction:
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
Match the following examples with their association to the Michael reaction:
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
Match the following statements with their involvement in the mechanism of the Michael addition reaction:
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
Match the following terms with their descriptions:
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
Match the following nucleophiles with their involvement in the Michael addition reaction:
Water = Nucleophile in Michael addition Alcohols = Nucleophile in Michael addition Amines = Nucleophile in Michael addition Enamines = Nucleophile in Michael addition
Match the following terms with their role in the Michael addition reaction:
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
Match the following researchers with their contributions to the Michael addition reaction:
Arthur Michael = Conducted research on the Michael reaction in 1887 Conrad & 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
Match the following examples with their association to the Michael reaction:
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
Match the following statements with their involvement in the mechanism of the Michael addition reaction:
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
Match the following groups with their role in the Michael addition reaction:
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
Study Notes
Michael Addition Reaction: Key Points
- Nucleophiles in Michael addition include doubly stabilized carbon nucleophiles and non-carbon nucleophiles such as water, alcohols, amines, and enamines.
- Some authors broaden the definition of the Michael addition to include any 1,4-addition reaction of α,β-unsaturated carbonyl compounds, while others limit it to the formation of carbon–carbon bonds through the addition of carbon nucleophiles.
- The terms oxa-Michael reaction and aza-Michael reaction refer to the 1,4-addition of oxygen and nitrogen nucleophiles, respectively.
- The Michael reaction has also been associated with 1,6-addition reactions.
- In the reaction mechanism, deprotonation of a nucleophile by a base leads to the formation of carbanion, which then reacts with the electrophilic alkene to form the product in a conjugate addition reaction.
- The Michael reaction proceeds via an enol or enolate nucleophile, and the reaction may be catalytic in base and irreversible at low temperature.
- The research on the Michael reaction was done by Arthur Michael in 1887, prompted by an 1884 publication by Conrad & Kuthzeit, but Rainer Ludwig Claisen claimed priority for the invention, which was later refuted.
- Researchers have expanded the scope of Michael additions to include elements of chirality via asymmetric versions of the reaction using chiral phase transfer catalysis or organocatalysis.
- Classical examples of the Michael reaction include the reaction between diethyl malonate and diethyl fumarate, diethyl malonate and mesityl oxide, and 2-nitropropane and methyl acrylate.
- The Mukaiyama–Michael addition involves a silyl enol ether as the nucleophile and titanium tetrachloride as the catalyst.
- The 1,6-Michael reaction proceeds via nucleophilic attack on the 𝛿 carbon of an α,β- 𝛿-diunsaturated Michael acceptor, and organocatalysis often favors the 1,4-addition.
- A well-known example of the Michael reaction is the synthesis of warfarin from 4-hydroxycoumarin and benzylideneacetone, and several asymmetric versions of this reaction exist using chiral catalysts.
Michael Addition Reaction: Key Points
- Nucleophiles in Michael addition include doubly stabilized carbon nucleophiles and non-carbon nucleophiles such as water, alcohols, amines, and enamines.
- Some authors broaden the definition of the Michael addition to include any 1,4-addition reaction of α,β-unsaturated carbonyl compounds, while others limit it to the formation of carbon–carbon bonds through the addition of carbon nucleophiles.
- The terms oxa-Michael reaction and aza-Michael reaction refer to the 1,4-addition of oxygen and nitrogen nucleophiles, respectively.
- The Michael reaction has also been associated with 1,6-addition reactions.
- In the reaction mechanism, deprotonation of a nucleophile by a base leads to the formation of carbanion, which then reacts with the electrophilic alkene to form the product in a conjugate addition reaction.
- The Michael reaction proceeds via an enol or enolate nucleophile, and the reaction may be catalytic in base and irreversible at low temperature.
- The research on the Michael reaction was done by Arthur Michael in 1887, prompted by an 1884 publication by Conrad & Kuthzeit, but Rainer Ludwig Claisen claimed priority for the invention, which was later refuted.
- Researchers have expanded the scope of Michael additions to include elements of chirality via asymmetric versions of the reaction using chiral phase transfer catalysis or organocatalysis.
- Classical examples of the Michael reaction include the reaction between diethyl malonate and diethyl fumarate, diethyl malonate and mesityl oxide, and 2-nitropropane and methyl acrylate.
- The Mukaiyama–Michael addition involves a silyl enol ether as the nucleophile and titanium tetrachloride as the catalyst.
- The 1,6-Michael reaction proceeds via nucleophilic attack on the 𝛿 carbon of an α,β- 𝛿-diunsaturated Michael acceptor, and organocatalysis often favors the 1,4-addition.
- A well-known example of the Michael reaction is the synthesis of warfarin from 4-hydroxycoumarin and benzylideneacetone, and several asymmetric versions of this reaction exist using chiral catalysts.
Test your knowledge of the key points of Michael addition reaction with this quiz. Explore the types of nucleophiles involved, reaction mechanisms, historical background, and classical examples. Sharpen your understanding of this important organic reaction.
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