SlideShare une entreprise Scribd logo
1  sur  18
Michael Addition :
Michael reaction or Michael addition is the 1,4- addition of a nucleophile to an electron-
deficient alkene, alkyne, or α-,β-unsaturated system in presence of a base. This is also known
as conjugated addition.
Michael Addition :
The nucleophiles are called donors.Malonates, nitroalkanes, cyanoacetic esters, acetoacetic
esters, and various β-ketoesters are all donors.
Electron deficient alkenes or alkynes or α-,β-unsaturated system act as acceptor.
Initially, unsaturated carbonyl compounds were utilized, but this was later expanded to
include other forms of electron deficient alkenes or alkynes.
In general, Michael addition reactions take place in neutral medium at room temperature
without the use of a catalyst.
The addition of a CH-acidic reagent to the carbon-carbon double bond of an α-,β -
unsaturated carbonyl compound is the overall procedure.
Michael addition reaction examples
Let’s see some examples of this reaction.
Michael Addition :
Michael reaction mechanism
Michael reaction mechanism completes in the following steps:
Step 1: The base abstracts alpha-acidic hydrogen from the nucleophile to form
carbanion which is resonance stabilized.
Michael Addition :
Step 2: The carbanion attacks the electron-deficient compounds.
Application of michael addition reaction
The Michael addition reaction is a very useful organic reaction and it is used in the
synthesis of natural products and drugs in organic chemistry.
Mannich Reaction :
Mannich reaction is a multicomponent condensation between an enolizable carbonyl
compound, a non-enolizable carbonyl compound, and an amine to form a β-amino carbonyl
compound or β-Amino Ketone or β-amino ester.
The enolizable carbonyl compound acts as a donor and the non-enolizable carbonyl compound
acts as an acceptor. The amine may be primary or secondary and generally ammonia as well
(not tertiary amine). Mostly, formaldehyde is used as a non-enolizable carbonyl compound.
Those aldehyde or ketones having alpha-hydrogen are enolizable and those with no alpha-
hydrogen are called non-enolizable carbonyl compounds.
This reaction can be performed under both acidic and basic condition.
Mannich Reaction :
Mannich reaction mechanism
The mechanism of the mannich reaction can be explained in both acidic and basic conditions.
A. Mechanism Under the acidic condition
Step 1: Nucleophilic addition of amine or ammonia to non-enolizable carbonyl compounds
followed by protonation to give an adduct known as iminium ion.
Mannich Reaction :
Step 2: Enolization of the enolizable carbonyl compound.
Mannich Reaction :
Step 3: The iminium ion reacts with enol formed in step 2 to give Mannich base
-amino carbonyl compound
Mannich Reaction :
B. Mechanism under the basic condition
Step 1: Nucleophilic addition of an amine to a non-enolizable carbonyl compound.
Mannich Reaction :
Step 2: Base abstracts hydrogen from enolizable carbonyl compound to form enolate.
Step 3: Reaction between enolate and iminium takes place.
Mannich Reaction :
In organic synthesis, Mannich bases are valuable intermediates. When amine is removed,
α,β-unsaturated carbonyl molecule is formed.
Another important application of the Mannich base is in alkylation. These are used as
alkylating agents. Similarly, the reaction with organolithium and organomagnesium
compounds gives β-amino alcohols, which shows pharmacological activities.
Mannich reaction plays an important role in Pharmaceutical chemistry. For example,
tropinone and alkaloids can be synthesized by using this reaction.
Diels Alder Reaction : (1928)
The Diels alder reaction is an electrocyclic [4+2]-cycloaddition reaction that produces an
unsaturated six-membered ring by combining conjugated dienes with dienophiles such as
alkenes or alkynes. This reaction is also known as Diels alder cycloaddition reaction.
Dienophiles are electron-deficient species, whereas diene is an electron-rich one. As a result,
the electron-donating group in the diene favors the reaction, while the electron-withdrawing
group on the dinophile speeds up the process
The reactivity of dienes is further enhanced by the presence of electron-releasing groups such
as alkyl, phenyl, or alkoxy groups.
Diels Alder Reaction :
Dinophiles are electron-poor species such as alkenes and alkynes. One or more electron-
withdrawing groups shift electron density away from the Pie-bond in a good dinophile. Some
examples of dinophiles are conjugated carbonyl compounds, nitro compounds, nitriles, vinyl
ethers, etc.
Examples of dinophiles
Diels-Alder reaction mechanism is a concerted process in which all bond formation and bond
breaking take place at the same time.
Mechanism :
Diels Alder Reaction :
It is believed that the mechanism of diels alder reaction involves the radical mechanism in
which diradical intermediate is formed. Let’s see such a mechanism.
Industrial applications of the diels alder reaction
The diels alder reaction is mainly used for synthesizing the six-membered ring. Further, it has
been reported that its industrial use in the production of pharmacologically active compounds,
agrochemicals, cosmetics, and odors.
Reformatsky reaction:
The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones, with
α-halo esters, using a metallic zinc to form β-hydroxy-esters:
The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an
alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates
or Grignard reagents and hence nucleophilic addition to the ester group does not occur. The
reaction was discovered by Sergey Nikolaevich Reformatsky.
Reaction Mechanism
Zinc metal is inserted into the carbon-halogen bond of the α-haloester by oxidative addition
1. This compound dimerizes and rearranges to form two zinc enolates 2. The oxygen on an
aldehyde or ketone coordinates to the zinc to form the six-member chair like transition state
3. A rearrangement occurs in which zinc switches to the aldehyde or ketone oxygen and a
carbon-carbon bond is formed 4. Acid workup 5,6 removes zinc to yield zinc(II) salts and a β-
hydroxy-ester 7.
Reformatsky reaction:
Uses of reformatsky reaction
The main application of the reformatsky reaction is to prepare β-hydroxy ester from
aldehyde or ketones.
Reformatsky reaction:
Reformatsky reaction:

Contenu connexe

Similaire à Name-Reaction-2 (1).pptx

Chapter 3 Alkenes and Alkynes
Chapter 3 Alkenes and AlkynesChapter 3 Alkenes and Alkynes
Chapter 3 Alkenes and Alkyneselfisusanti
 
Reaction mechanism ppt for advance organic chemistry.pptx
Reaction mechanism ppt for advance organic chemistry.pptxReaction mechanism ppt for advance organic chemistry.pptx
Reaction mechanism ppt for advance organic chemistry.pptxDiwakar Mishra
 
Aromatic Electrophilic Substitution Reactions
Aromatic Electrophilic Substitution ReactionsAromatic Electrophilic Substitution Reactions
Aromatic Electrophilic Substitution ReactionsTamralipta Mahavidyalaya
 
Assingment 2 rl no. 5209 e2 ene reaction.ppt
Assingment 2 rl no. 5209 e2  ene reaction.pptAssingment 2 rl no. 5209 e2  ene reaction.ppt
Assingment 2 rl no. 5209 e2 ene reaction.pptJabrilHaad
 
REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).imranjan5261
 
Organic chemistry reactions
Organic chemistry reactionsOrganic chemistry reactions
Organic chemistry reactionssameera patel
 
M.Sc. Sem-II, P-III, Unit-I.pptx
M.Sc. Sem-II, P-III, Unit-I.pptxM.Sc. Sem-II, P-III, Unit-I.pptx
M.Sc. Sem-II, P-III, Unit-I.pptxOMKARVANI1
 
Enols & Enolates
Enols & EnolatesEnols & Enolates
Enols & EnolatesKhan Firoz
 
Organicreactionsandmechanisms 120331092608-phpapp01
Organicreactionsandmechanisms 120331092608-phpapp01Organicreactionsandmechanisms 120331092608-phpapp01
Organicreactionsandmechanisms 120331092608-phpapp01Yogesh Kaddipudi
 
Most Important Reactions Mechanism of Organic Chemistry
Most Important Reactions Mechanism of Organic ChemistryMost Important Reactions Mechanism of Organic Chemistry
Most Important Reactions Mechanism of Organic ChemistryAymed Zucc'nt
 
Carboxylic Acids.pptx
Carboxylic Acids.pptxCarboxylic Acids.pptx
Carboxylic Acids.pptxMarMary6
 
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-III
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-IIIUnit V: Reaction of synthetic importance as per PCI Syllabus of POC-III
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-IIIGanesh Mote
 
nucleophilic addition reaction sem ii poc i
nucleophilic addition reaction sem ii poc inucleophilic addition reaction sem ii poc i
nucleophilic addition reaction sem ii poc iAtulBendale2
 
Introduction to Organic Chemistry.pdf
Introduction to Organic Chemistry.pdfIntroduction to Organic Chemistry.pdf
Introduction to Organic Chemistry.pdfmansoorahmed989397
 
Suzuki and Shapiro reaction
Suzuki and Shapiro reaction Suzuki and Shapiro reaction
Suzuki and Shapiro reaction Shalinee Chandra
 
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptx
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptxLecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptx
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptxEsayDawit
 

Similaire à Name-Reaction-2 (1).pptx (20)

Chapter 3 Alkenes and Alkynes
Chapter 3 Alkenes and AlkynesChapter 3 Alkenes and Alkynes
Chapter 3 Alkenes and Alkynes
 
Reaction mechanism ppt for advance organic chemistry.pptx
Reaction mechanism ppt for advance organic chemistry.pptxReaction mechanism ppt for advance organic chemistry.pptx
Reaction mechanism ppt for advance organic chemistry.pptx
 
Condensation reactions
Condensation reactions Condensation reactions
Condensation reactions
 
Aromatic Electrophilic Substitution Reactions
Aromatic Electrophilic Substitution ReactionsAromatic Electrophilic Substitution Reactions
Aromatic Electrophilic Substitution Reactions
 
Assingment 2 rl no. 5209 e2 ene reaction.ppt
Assingment 2 rl no. 5209 e2  ene reaction.pptAssingment 2 rl no. 5209 e2  ene reaction.ppt
Assingment 2 rl no. 5209 e2 ene reaction.ppt
 
REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).
 
aromatic reactions.pptx
aromatic reactions.pptxaromatic reactions.pptx
aromatic reactions.pptx
 
ALDEHYDES AND KETONES
ALDEHYDES AND KETONESALDEHYDES AND KETONES
ALDEHYDES AND KETONES
 
Organic chemistry reactions
Organic chemistry reactionsOrganic chemistry reactions
Organic chemistry reactions
 
M.Sc. Sem-II, P-III, Unit-I.pptx
M.Sc. Sem-II, P-III, Unit-I.pptxM.Sc. Sem-II, P-III, Unit-I.pptx
M.Sc. Sem-II, P-III, Unit-I.pptx
 
Enols & Enolates
Enols & EnolatesEnols & Enolates
Enols & Enolates
 
Organicreactionsandmechanisms 120331092608-phpapp01
Organicreactionsandmechanisms 120331092608-phpapp01Organicreactionsandmechanisms 120331092608-phpapp01
Organicreactionsandmechanisms 120331092608-phpapp01
 
Latha Chemistry ppt.pptx
Latha Chemistry ppt.pptxLatha Chemistry ppt.pptx
Latha Chemistry ppt.pptx
 
Most Important Reactions Mechanism of Organic Chemistry
Most Important Reactions Mechanism of Organic ChemistryMost Important Reactions Mechanism of Organic Chemistry
Most Important Reactions Mechanism of Organic Chemistry
 
Carboxylic Acids.pptx
Carboxylic Acids.pptxCarboxylic Acids.pptx
Carboxylic Acids.pptx
 
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-III
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-IIIUnit V: Reaction of synthetic importance as per PCI Syllabus of POC-III
Unit V: Reaction of synthetic importance as per PCI Syllabus of POC-III
 
nucleophilic addition reaction sem ii poc i
nucleophilic addition reaction sem ii poc inucleophilic addition reaction sem ii poc i
nucleophilic addition reaction sem ii poc i
 
Introduction to Organic Chemistry.pdf
Introduction to Organic Chemistry.pdfIntroduction to Organic Chemistry.pdf
Introduction to Organic Chemistry.pdf
 
Suzuki and Shapiro reaction
Suzuki and Shapiro reaction Suzuki and Shapiro reaction
Suzuki and Shapiro reaction
 
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptx
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptxLecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptx
Lecture_note_3_Reaction_of_Carbon_Nucleophile_with_Carbonyl_Groups (1).pptx
 

Dernier

Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 b
Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 bAsymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 b
Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 bSérgio Sacani
 
Factory Acceptance Test( FAT).pptx .
Factory Acceptance Test( FAT).pptx       .Factory Acceptance Test( FAT).pptx       .
Factory Acceptance Test( FAT).pptx .Poonam Aher Patil
 
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance Booking
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance BookingCall Girls Alandi Call Me 7737669865 Budget Friendly No Advance Booking
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance Bookingroncy bisnoi
 
GBSN - Biochemistry (Unit 1)
GBSN - Biochemistry (Unit 1)GBSN - Biochemistry (Unit 1)
GBSN - Biochemistry (Unit 1)Areesha Ahmad
 
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...Mohammad Khajehpour
 
COST ESTIMATION FOR A RESEARCH PROJECT.pptx
COST ESTIMATION FOR A RESEARCH PROJECT.pptxCOST ESTIMATION FOR A RESEARCH PROJECT.pptx
COST ESTIMATION FOR A RESEARCH PROJECT.pptxFarihaAbdulRasheed
 
Zoology 5th semester notes( Sumit_yadav).pdf
Zoology 5th semester notes( Sumit_yadav).pdfZoology 5th semester notes( Sumit_yadav).pdf
Zoology 5th semester notes( Sumit_yadav).pdfSumit Kumar yadav
 
Bacterial Identification and Classifications
Bacterial Identification and ClassificationsBacterial Identification and Classifications
Bacterial Identification and ClassificationsAreesha Ahmad
 
PSYCHOSOCIAL NEEDS. in nursing II sem pptx
PSYCHOSOCIAL NEEDS. in nursing II sem pptxPSYCHOSOCIAL NEEDS. in nursing II sem pptx
PSYCHOSOCIAL NEEDS. in nursing II sem pptxSuji236384
 
pumpkin fruit fly, water melon fruit fly, cucumber fruit fly
pumpkin fruit fly, water melon fruit fly, cucumber fruit flypumpkin fruit fly, water melon fruit fly, cucumber fruit fly
pumpkin fruit fly, water melon fruit fly, cucumber fruit flyPRADYUMMAURYA1
 
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.Nitya salvi
 
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...Chemical Tests; flame test, positive and negative ions test Edexcel Internati...
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...ssuser79fe74
 
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptx
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptxSCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptx
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptxRizalinePalanog2
 
Pulmonary drug delivery system M.pharm -2nd sem P'ceutics
Pulmonary drug delivery system M.pharm -2nd sem P'ceuticsPulmonary drug delivery system M.pharm -2nd sem P'ceutics
Pulmonary drug delivery system M.pharm -2nd sem P'ceuticssakshisoni2385
 
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdf
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdfPests of cotton_Borer_Pests_Binomics_Dr.UPR.pdf
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdfPirithiRaju
 
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)Joonhun Lee
 
Unit5-Cloud.pptx for lpu course cse121 o
Unit5-Cloud.pptx for lpu course cse121 oUnit5-Cloud.pptx for lpu course cse121 o
Unit5-Cloud.pptx for lpu course cse121 oManavSingh202607
 
module for grade 9 for distance learning
module for grade 9 for distance learningmodule for grade 9 for distance learning
module for grade 9 for distance learninglevieagacer
 

Dernier (20)

CELL -Structural and Functional unit of life.pdf
CELL -Structural and Functional unit of life.pdfCELL -Structural and Functional unit of life.pdf
CELL -Structural and Functional unit of life.pdf
 
Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 b
Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 bAsymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 b
Asymmetry in the atmosphere of the ultra-hot Jupiter WASP-76 b
 
Factory Acceptance Test( FAT).pptx .
Factory Acceptance Test( FAT).pptx       .Factory Acceptance Test( FAT).pptx       .
Factory Acceptance Test( FAT).pptx .
 
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance Booking
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance BookingCall Girls Alandi Call Me 7737669865 Budget Friendly No Advance Booking
Call Girls Alandi Call Me 7737669865 Budget Friendly No Advance Booking
 
GBSN - Biochemistry (Unit 1)
GBSN - Biochemistry (Unit 1)GBSN - Biochemistry (Unit 1)
GBSN - Biochemistry (Unit 1)
 
Site Acceptance Test .
Site Acceptance Test                    .Site Acceptance Test                    .
Site Acceptance Test .
 
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...
Dopamine neurotransmitter determination using graphite sheet- graphene nano-s...
 
COST ESTIMATION FOR A RESEARCH PROJECT.pptx
COST ESTIMATION FOR A RESEARCH PROJECT.pptxCOST ESTIMATION FOR A RESEARCH PROJECT.pptx
COST ESTIMATION FOR A RESEARCH PROJECT.pptx
 
Zoology 5th semester notes( Sumit_yadav).pdf
Zoology 5th semester notes( Sumit_yadav).pdfZoology 5th semester notes( Sumit_yadav).pdf
Zoology 5th semester notes( Sumit_yadav).pdf
 
Bacterial Identification and Classifications
Bacterial Identification and ClassificationsBacterial Identification and Classifications
Bacterial Identification and Classifications
 
PSYCHOSOCIAL NEEDS. in nursing II sem pptx
PSYCHOSOCIAL NEEDS. in nursing II sem pptxPSYCHOSOCIAL NEEDS. in nursing II sem pptx
PSYCHOSOCIAL NEEDS. in nursing II sem pptx
 
pumpkin fruit fly, water melon fruit fly, cucumber fruit fly
pumpkin fruit fly, water melon fruit fly, cucumber fruit flypumpkin fruit fly, water melon fruit fly, cucumber fruit fly
pumpkin fruit fly, water melon fruit fly, cucumber fruit fly
 
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.
❤Jammu Kashmir Call Girls 8617697112 Personal Whatsapp Number 💦✅.
 
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...Chemical Tests; flame test, positive and negative ions test Edexcel Internati...
Chemical Tests; flame test, positive and negative ions test Edexcel Internati...
 
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptx
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptxSCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptx
SCIENCE-4-QUARTER4-WEEK-4-PPT-1 (1).pptx
 
Pulmonary drug delivery system M.pharm -2nd sem P'ceutics
Pulmonary drug delivery system M.pharm -2nd sem P'ceuticsPulmonary drug delivery system M.pharm -2nd sem P'ceutics
Pulmonary drug delivery system M.pharm -2nd sem P'ceutics
 
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdf
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdfPests of cotton_Borer_Pests_Binomics_Dr.UPR.pdf
Pests of cotton_Borer_Pests_Binomics_Dr.UPR.pdf
 
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)
Feature-aligned N-BEATS with Sinkhorn divergence (ICLR '24)
 
Unit5-Cloud.pptx for lpu course cse121 o
Unit5-Cloud.pptx for lpu course cse121 oUnit5-Cloud.pptx for lpu course cse121 o
Unit5-Cloud.pptx for lpu course cse121 o
 
module for grade 9 for distance learning
module for grade 9 for distance learningmodule for grade 9 for distance learning
module for grade 9 for distance learning
 

Name-Reaction-2 (1).pptx

  • 1. Michael Addition : Michael reaction or Michael addition is the 1,4- addition of a nucleophile to an electron- deficient alkene, alkyne, or α-,β-unsaturated system in presence of a base. This is also known as conjugated addition.
  • 2. Michael Addition : The nucleophiles are called donors.Malonates, nitroalkanes, cyanoacetic esters, acetoacetic esters, and various β-ketoesters are all donors. Electron deficient alkenes or alkynes or α-,β-unsaturated system act as acceptor. Initially, unsaturated carbonyl compounds were utilized, but this was later expanded to include other forms of electron deficient alkenes or alkynes. In general, Michael addition reactions take place in neutral medium at room temperature without the use of a catalyst. The addition of a CH-acidic reagent to the carbon-carbon double bond of an α-,β - unsaturated carbonyl compound is the overall procedure. Michael addition reaction examples Let’s see some examples of this reaction.
  • 3. Michael Addition : Michael reaction mechanism Michael reaction mechanism completes in the following steps: Step 1: The base abstracts alpha-acidic hydrogen from the nucleophile to form carbanion which is resonance stabilized.
  • 4. Michael Addition : Step 2: The carbanion attacks the electron-deficient compounds. Application of michael addition reaction The Michael addition reaction is a very useful organic reaction and it is used in the synthesis of natural products and drugs in organic chemistry.
  • 5. Mannich Reaction : Mannich reaction is a multicomponent condensation between an enolizable carbonyl compound, a non-enolizable carbonyl compound, and an amine to form a β-amino carbonyl compound or β-Amino Ketone or β-amino ester. The enolizable carbonyl compound acts as a donor and the non-enolizable carbonyl compound acts as an acceptor. The amine may be primary or secondary and generally ammonia as well (not tertiary amine). Mostly, formaldehyde is used as a non-enolizable carbonyl compound. Those aldehyde or ketones having alpha-hydrogen are enolizable and those with no alpha- hydrogen are called non-enolizable carbonyl compounds. This reaction can be performed under both acidic and basic condition.
  • 6. Mannich Reaction : Mannich reaction mechanism The mechanism of the mannich reaction can be explained in both acidic and basic conditions. A. Mechanism Under the acidic condition Step 1: Nucleophilic addition of amine or ammonia to non-enolizable carbonyl compounds followed by protonation to give an adduct known as iminium ion.
  • 7. Mannich Reaction : Step 2: Enolization of the enolizable carbonyl compound.
  • 8. Mannich Reaction : Step 3: The iminium ion reacts with enol formed in step 2 to give Mannich base -amino carbonyl compound
  • 9. Mannich Reaction : B. Mechanism under the basic condition Step 1: Nucleophilic addition of an amine to a non-enolizable carbonyl compound.
  • 10. Mannich Reaction : Step 2: Base abstracts hydrogen from enolizable carbonyl compound to form enolate. Step 3: Reaction between enolate and iminium takes place.
  • 11. Mannich Reaction : In organic synthesis, Mannich bases are valuable intermediates. When amine is removed, α,β-unsaturated carbonyl molecule is formed. Another important application of the Mannich base is in alkylation. These are used as alkylating agents. Similarly, the reaction with organolithium and organomagnesium compounds gives β-amino alcohols, which shows pharmacological activities. Mannich reaction plays an important role in Pharmaceutical chemistry. For example, tropinone and alkaloids can be synthesized by using this reaction.
  • 12. Diels Alder Reaction : (1928) The Diels alder reaction is an electrocyclic [4+2]-cycloaddition reaction that produces an unsaturated six-membered ring by combining conjugated dienes with dienophiles such as alkenes or alkynes. This reaction is also known as Diels alder cycloaddition reaction. Dienophiles are electron-deficient species, whereas diene is an electron-rich one. As a result, the electron-donating group in the diene favors the reaction, while the electron-withdrawing group on the dinophile speeds up the process The reactivity of dienes is further enhanced by the presence of electron-releasing groups such as alkyl, phenyl, or alkoxy groups.
  • 13. Diels Alder Reaction : Dinophiles are electron-poor species such as alkenes and alkynes. One or more electron- withdrawing groups shift electron density away from the Pie-bond in a good dinophile. Some examples of dinophiles are conjugated carbonyl compounds, nitro compounds, nitriles, vinyl ethers, etc. Examples of dinophiles Diels-Alder reaction mechanism is a concerted process in which all bond formation and bond breaking take place at the same time. Mechanism :
  • 14. Diels Alder Reaction : It is believed that the mechanism of diels alder reaction involves the radical mechanism in which diradical intermediate is formed. Let’s see such a mechanism. Industrial applications of the diels alder reaction The diels alder reaction is mainly used for synthesizing the six-membered ring. Further, it has been reported that its industrial use in the production of pharmacologically active compounds, agrochemicals, cosmetics, and odors.
  • 15. Reformatsky reaction: The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones, with α-halo esters, using a metallic zinc to form β-hydroxy-esters: The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates or Grignard reagents and hence nucleophilic addition to the ester group does not occur. The reaction was discovered by Sergey Nikolaevich Reformatsky. Reaction Mechanism Zinc metal is inserted into the carbon-halogen bond of the α-haloester by oxidative addition 1. This compound dimerizes and rearranges to form two zinc enolates 2. The oxygen on an aldehyde or ketone coordinates to the zinc to form the six-member chair like transition state 3. A rearrangement occurs in which zinc switches to the aldehyde or ketone oxygen and a carbon-carbon bond is formed 4. Acid workup 5,6 removes zinc to yield zinc(II) salts and a β- hydroxy-ester 7.
  • 16. Reformatsky reaction: Uses of reformatsky reaction The main application of the reformatsky reaction is to prepare β-hydroxy ester from aldehyde or ketones.