SlideShare a Scribd company logo
Beckmann Rearrangement
Persented by
Dinesh yadav
2017PCY5358 1
Submitted to:-
Dr. Ragini Gupta
Prof.&HOD
Dept. of Chemistry
Beckmann rearrangement
• The acid-catalysed conversion of ketoximes to amides is
known as the Beckmann rearrangement
• The Beckmann rearrangement, named after the German
chemist Ernst Otto Beckmann (1853–1923)
• This rearrangement is occurs in both cyclic and acyclic
compounds .
• Aldoximes are less reactive.
• Cyclic oximes yield lactams and acyclic oximes yield amides
2J. Am. Chem. Soc., 1924, 46 (6), pp 1477–1483 DOI: 10.1021/ja01671a018
Beckmann rearrangement
3
Reagents:-
Conc.H2SO4, HCl, PCl5, PCl3, SOCl2, ZnO, SiO2, PPA
(Poly phosphoric acid) etc., are commonly employed in
Beckmann rearrangement.
Oxime Amide
J. Am. Chem. Soc., 1924, 46 (6), pp 1477–1483 DOI: 10.1021/ja01671a018
Reaction mechanism
The first step in the process is formation of an oxime from the
aldehyde or ketone,
4
Reaction mechanism
5
This rearrangement take place an alkyl migration with expulsion of
the hydroxyl group to form a nitrilium ion followed by hydrolysis.
Migratory aptitude
• The relative migratory aptitudes of different groups in Beckmann
rearrangement is illustrated below.
6
Applications in drug synthesis:-
• An alternative industrial synthesis method for Paracetamol.
It is involves direct acylation of phenol with acetic anhydride
catalyzed by HF, conversion of the ketone to a ketoxime
with hydroxylamine, followed by the acid-catalyzed Beckmann
rearrangement to give the amide
7
Paracetamol
Applications in drug synthesis:-
• The Beckmann rearrangement is also used in the
synthesis of
1. DHEA
2. Benazepril
3. Etazepine etc.
8
Applications in polymer synthesis:-
• Beckmann rearrangement can be rendered catalytic using cyanuric
chloride and zinc chloride as a co-catalyst. For
example, cyclododecanone can be converted to the
corresponding lactam, the monomer used in the production
of Nylon 12
9
Applications in polymer synthesis:-
• The Beckmann rearrangement is also used in
the synthesis of Nylon 6
10
THANK YOU.
11

More Related Content

What's hot

Heterocyclic compounds
Heterocyclic compoundsHeterocyclic compounds
Heterocyclic compounds
priyaswain27
 
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
Dr Venkatesh P
 
Fused heterocyclic compound indole
Fused heterocyclic compound indoleFused heterocyclic compound indole
Fused heterocyclic compound indole
Drx Mathivanan Selvam
 
Conformation of biphenyl compounds (Atropisomerism)
Conformation of biphenyl compounds (Atropisomerism)Conformation of biphenyl compounds (Atropisomerism)
Conformation of biphenyl compounds (Atropisomerism)
Drx Mathivanan Selvam
 
Schmidt rearrangement
Schmidt rearrangementSchmidt rearrangement
Schmidt rearrangement
Syed Touseef Haidar Gerdezi
 
Fused heterocyclic compounds quinoline
Fused heterocyclic compounds   quinolineFused heterocyclic compounds   quinoline
Fused heterocyclic compounds quinoline
Drx Mathivanan Selvam
 
Rearrangement of benzilic acid
Rearrangement of benzilic acidRearrangement of benzilic acid
Rearrangement of benzilic acid
araz aras
 
Seminar on name reaction
Seminar on name reactionSeminar on name reaction
Seminar on name reaction
nitin lambe
 
Fused heterocyclic componds acridine
Fused heterocyclic componds   acridineFused heterocyclic componds   acridine
Fused heterocyclic componds acridine
Drx Mathivanan Selvam
 
Birch reduction
Birch reductionBirch reduction
Birch reduction
School of Scholars
 
Practical Experiment 4: Benzyl from benzoin
Practical Experiment 4: Benzyl from benzoinPractical Experiment 4: Benzyl from benzoin
Practical Experiment 4: Benzyl from benzoin
SONALI PAWAR
 
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
Dr Venkatesh P
 
Birch reduction
Birch reductionBirch reduction
Birch reduction
Dr. Krishna Swamy. G
 
Quinoline and isoquinoline- heterocyclic chemistry- pharmacy
Quinoline and isoquinoline- heterocyclic chemistry- pharmacyQuinoline and isoquinoline- heterocyclic chemistry- pharmacy
Quinoline and isoquinoline- heterocyclic chemistry- pharmacy
Akhil Nagar
 
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
Dr Venkatesh P
 
Oxazole
OxazoleOxazole
Hofman rearrangement
Hofman rearrangement Hofman rearrangement
Hofman rearrangement
Madhusudan Bachute
 
Resolution of racemic mixture
Resolution of  racemic mixtureResolution of  racemic mixture
Resolution of racemic mixture
Iqrar Ansari
 
Biphenyl derivatives & Atropisomerism
Biphenyl derivatives & AtropisomerismBiphenyl derivatives & Atropisomerism
Biphenyl derivatives & Atropisomerism
PRUTHVIRAJ K
 
Benzil benzilic acid rearrangement
Benzil benzilic acid rearrangementBenzil benzilic acid rearrangement
Benzil benzilic acid rearrangement
Syed Touseef Haidar Gerdezi
 

What's hot (20)

Heterocyclic compounds
Heterocyclic compoundsHeterocyclic compounds
Heterocyclic compounds
 
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
Imidazole - Synthesis of Imidazole - Reactions of Imidazole - Medicinal uses ...
 
Fused heterocyclic compound indole
Fused heterocyclic compound indoleFused heterocyclic compound indole
Fused heterocyclic compound indole
 
Conformation of biphenyl compounds (Atropisomerism)
Conformation of biphenyl compounds (Atropisomerism)Conformation of biphenyl compounds (Atropisomerism)
Conformation of biphenyl compounds (Atropisomerism)
 
Schmidt rearrangement
Schmidt rearrangementSchmidt rearrangement
Schmidt rearrangement
 
Fused heterocyclic compounds quinoline
Fused heterocyclic compounds   quinolineFused heterocyclic compounds   quinoline
Fused heterocyclic compounds quinoline
 
Rearrangement of benzilic acid
Rearrangement of benzilic acidRearrangement of benzilic acid
Rearrangement of benzilic acid
 
Seminar on name reaction
Seminar on name reactionSeminar on name reaction
Seminar on name reaction
 
Fused heterocyclic componds acridine
Fused heterocyclic componds   acridineFused heterocyclic componds   acridine
Fused heterocyclic componds acridine
 
Birch reduction
Birch reductionBirch reduction
Birch reduction
 
Practical Experiment 4: Benzyl from benzoin
Practical Experiment 4: Benzyl from benzoinPractical Experiment 4: Benzyl from benzoin
Practical Experiment 4: Benzyl from benzoin
 
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
Thiazole - Synthesis of Thiazole - Reactions of Thiazole - Medicinal uses of ...
 
Birch reduction
Birch reductionBirch reduction
Birch reduction
 
Quinoline and isoquinoline- heterocyclic chemistry- pharmacy
Quinoline and isoquinoline- heterocyclic chemistry- pharmacyQuinoline and isoquinoline- heterocyclic chemistry- pharmacy
Quinoline and isoquinoline- heterocyclic chemistry- pharmacy
 
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
Heterocyclic compounds - Thiophene - Synthesis of Thiophene - Characteristic ...
 
Oxazole
OxazoleOxazole
Oxazole
 
Hofman rearrangement
Hofman rearrangement Hofman rearrangement
Hofman rearrangement
 
Resolution of racemic mixture
Resolution of  racemic mixtureResolution of  racemic mixture
Resolution of racemic mixture
 
Biphenyl derivatives & Atropisomerism
Biphenyl derivatives & AtropisomerismBiphenyl derivatives & Atropisomerism
Biphenyl derivatives & Atropisomerism
 
Benzil benzilic acid rearrangement
Benzil benzilic acid rearrangementBenzil benzilic acid rearrangement
Benzil benzilic acid rearrangement
 

Similar to Beckmann rearrangement ppt

Beckmann Rearrangement Y.K.pptx
Beckmann Rearrangement Y.K.pptxBeckmann Rearrangement Y.K.pptx
Beckmann Rearrangement Y.K.pptx
Yehtesham Khurshid
 
Beckmann rearrangement reaction
Beckmann rearrangement reactionBeckmann rearrangement reaction
Beckmann rearrangement reaction
MadishNiaz
 
Molecular rearrangements involving electron deficient nitrogen as an intermed...
Molecular rearrangements involving electron deficient nitrogen as an intermed...Molecular rearrangements involving electron deficient nitrogen as an intermed...
Molecular rearrangements involving electron deficient nitrogen as an intermed...
CCSU
 
Reaction of synthetic importance.ppt
Reaction of synthetic importance.pptReaction of synthetic importance.ppt
Reaction of synthetic importance.ppt
RAJARAMBAPU COLLEGE OF PHARMACY, KASEGAON
 
Beckmann rearrangement
Beckmann rearrangementBeckmann rearrangement
Beckmann rearrangement
Mano Bala
 
Rearrangement
RearrangementRearrangement
Rearrangement
Arvind Singh Heer
 
Mechanism & reaction
Mechanism & reactionMechanism & reaction
Mechanism & reaction
KIRAN DHANGAR
 
WOOD WARD FIESER RULE.pptx
WOOD WARD FIESER RULE.pptxWOOD WARD FIESER RULE.pptx
WOOD WARD FIESER RULE.pptx
SushmitaHiremath2
 
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptxWAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
IndrajitSamanta7
 
Baeyer villiger oxidation
Baeyer villiger oxidationBaeyer villiger oxidation
Baeyer villiger oxidation
andhra university
 
niketreaction-190310185849.pdf
niketreaction-190310185849.pdfniketreaction-190310185849.pdf
niketreaction-190310185849.pdf
GopiNath340181
 
The magic of cubane
The magic of cubaneThe magic of cubane
The magic of cubane
Anthony Melvin Crasto Ph.D
 
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptxCO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
Sri Lakshmi
 
organic reaction
organic reactionorganic reaction
organic reaction
NiketBajare
 
Baylis hilman
Baylis hilmanBaylis hilman
Baylis hilman
wadhava gurumeet
 
REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).
imranjan5261
 
Beckmann Rearrangement.pptx
Beckmann Rearrangement.pptxBeckmann Rearrangement.pptx
Beckmann Rearrangement.pptx
Jane756411
 
Sigmatropic reaction
Sigmatropic reactionSigmatropic reaction
Sigmatropic reaction
azamushahiullah prottoy
 
Lactam
Lactam Lactam
Lactam
Rabia Aziz
 
Rearrangement reactions
Rearrangement reactionsRearrangement reactions
Rearrangement reactions
MohammadHaider18
 

Similar to Beckmann rearrangement ppt (20)

Beckmann Rearrangement Y.K.pptx
Beckmann Rearrangement Y.K.pptxBeckmann Rearrangement Y.K.pptx
Beckmann Rearrangement Y.K.pptx
 
Beckmann rearrangement reaction
Beckmann rearrangement reactionBeckmann rearrangement reaction
Beckmann rearrangement reaction
 
Molecular rearrangements involving electron deficient nitrogen as an intermed...
Molecular rearrangements involving electron deficient nitrogen as an intermed...Molecular rearrangements involving electron deficient nitrogen as an intermed...
Molecular rearrangements involving electron deficient nitrogen as an intermed...
 
Reaction of synthetic importance.ppt
Reaction of synthetic importance.pptReaction of synthetic importance.ppt
Reaction of synthetic importance.ppt
 
Beckmann rearrangement
Beckmann rearrangementBeckmann rearrangement
Beckmann rearrangement
 
Rearrangement
RearrangementRearrangement
Rearrangement
 
Mechanism & reaction
Mechanism & reactionMechanism & reaction
Mechanism & reaction
 
WOOD WARD FIESER RULE.pptx
WOOD WARD FIESER RULE.pptxWOOD WARD FIESER RULE.pptx
WOOD WARD FIESER RULE.pptx
 
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptxWAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
WAGNER-MEERWEIN REARRANGEMENT 123 [Autosaved].pptx
 
Baeyer villiger oxidation
Baeyer villiger oxidationBaeyer villiger oxidation
Baeyer villiger oxidation
 
niketreaction-190310185849.pdf
niketreaction-190310185849.pdfniketreaction-190310185849.pdf
niketreaction-190310185849.pdf
 
The magic of cubane
The magic of cubaneThe magic of cubane
The magic of cubane
 
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptxCO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
CO-1_INTRODUCTIONsession-3_ANTIBIOTICS.pptx
 
organic reaction
organic reactionorganic reaction
organic reaction
 
Baylis hilman
Baylis hilmanBaylis hilman
Baylis hilman
 
REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).REACTIONS.of organic chemistry pptx (.).
REACTIONS.of organic chemistry pptx (.).
 
Beckmann Rearrangement.pptx
Beckmann Rearrangement.pptxBeckmann Rearrangement.pptx
Beckmann Rearrangement.pptx
 
Sigmatropic reaction
Sigmatropic reactionSigmatropic reaction
Sigmatropic reaction
 
Lactam
Lactam Lactam
Lactam
 
Rearrangement reactions
Rearrangement reactionsRearrangement reactions
Rearrangement reactions
 

Recently uploaded

Lateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensiveLateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensive
silvermistyshot
 
The ASGCT Annual Meeting was packed with exciting progress in the field advan...
The ASGCT Annual Meeting was packed with exciting progress in the field advan...The ASGCT Annual Meeting was packed with exciting progress in the field advan...
The ASGCT Annual Meeting was packed with exciting progress in the field advan...
Health Advances
 
Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.
Nistarini College, Purulia (W.B) India
 
SCHIZOPHRENIA Disorder/ Brain Disorder.pdf
SCHIZOPHRENIA Disorder/ Brain Disorder.pdfSCHIZOPHRENIA Disorder/ Brain Disorder.pdf
SCHIZOPHRENIA Disorder/ Brain Disorder.pdf
SELF-EXPLANATORY
 
Leaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdfLeaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdf
RenuJangid3
 
Richard's entangled aventures in wonderland
Richard's entangled aventures in wonderlandRichard's entangled aventures in wonderland
Richard's entangled aventures in wonderland
Richard Gill
 
platelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptxplatelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptx
muralinath2
 
Comparative structure of adrenal gland in vertebrates
Comparative structure of adrenal gland in vertebratesComparative structure of adrenal gland in vertebrates
Comparative structure of adrenal gland in vertebrates
sachin783648
 
GBSN - Microbiology (Lab 4) Culture Media
GBSN - Microbiology (Lab 4) Culture MediaGBSN - Microbiology (Lab 4) Culture Media
GBSN - Microbiology (Lab 4) Culture Media
Areesha Ahmad
 
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
Ana Luísa Pinho
 
platelets- lifespan -Clot retraction-disorders.pptx
platelets- lifespan -Clot retraction-disorders.pptxplatelets- lifespan -Clot retraction-disorders.pptx
platelets- lifespan -Clot retraction-disorders.pptx
muralinath2
 
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
Sérgio Sacani
 
RNA INTERFERENCE: UNRAVELING GENETIC SILENCING
RNA INTERFERENCE: UNRAVELING GENETIC SILENCINGRNA INTERFERENCE: UNRAVELING GENETIC SILENCING
RNA INTERFERENCE: UNRAVELING GENETIC SILENCING
AADYARAJPANDEY1
 
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
NathanBaughman3
 
insect taxonomy importance systematics and classification
insect taxonomy importance systematics and classificationinsect taxonomy importance systematics and classification
insect taxonomy importance systematics and classification
anitaento25
 
extra-chromosomal-inheritance[1].pptx.pdfpdf
extra-chromosomal-inheritance[1].pptx.pdfpdfextra-chromosomal-inheritance[1].pptx.pdfpdf
extra-chromosomal-inheritance[1].pptx.pdfpdf
DiyaBiswas10
 
erythropoiesis-I_mechanism& clinical significance.pptx
erythropoiesis-I_mechanism& clinical significance.pptxerythropoiesis-I_mechanism& clinical significance.pptx
erythropoiesis-I_mechanism& clinical significance.pptx
muralinath2
 
Seminar of U.V. Spectroscopy by SAMIR PANDA
 Seminar of U.V. Spectroscopy by SAMIR PANDA Seminar of U.V. Spectroscopy by SAMIR PANDA
Seminar of U.V. Spectroscopy by SAMIR PANDA
SAMIR PANDA
 
Hemoglobin metabolism_pathophysiology.pptx
Hemoglobin metabolism_pathophysiology.pptxHemoglobin metabolism_pathophysiology.pptx
Hemoglobin metabolism_pathophysiology.pptx
muralinath2
 
GBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram StainingGBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram Staining
Areesha Ahmad
 

Recently uploaded (20)

Lateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensiveLateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensive
 
The ASGCT Annual Meeting was packed with exciting progress in the field advan...
The ASGCT Annual Meeting was packed with exciting progress in the field advan...The ASGCT Annual Meeting was packed with exciting progress in the field advan...
The ASGCT Annual Meeting was packed with exciting progress in the field advan...
 
Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.
 
SCHIZOPHRENIA Disorder/ Brain Disorder.pdf
SCHIZOPHRENIA Disorder/ Brain Disorder.pdfSCHIZOPHRENIA Disorder/ Brain Disorder.pdf
SCHIZOPHRENIA Disorder/ Brain Disorder.pdf
 
Leaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdfLeaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdf
 
Richard's entangled aventures in wonderland
Richard's entangled aventures in wonderlandRichard's entangled aventures in wonderland
Richard's entangled aventures in wonderland
 
platelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptxplatelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptx
 
Comparative structure of adrenal gland in vertebrates
Comparative structure of adrenal gland in vertebratesComparative structure of adrenal gland in vertebrates
Comparative structure of adrenal gland in vertebrates
 
GBSN - Microbiology (Lab 4) Culture Media
GBSN - Microbiology (Lab 4) Culture MediaGBSN - Microbiology (Lab 4) Culture Media
GBSN - Microbiology (Lab 4) Culture Media
 
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
Deep Behavioral Phenotyping in Systems Neuroscience for Functional Atlasing a...
 
platelets- lifespan -Clot retraction-disorders.pptx
platelets- lifespan -Clot retraction-disorders.pptxplatelets- lifespan -Clot retraction-disorders.pptx
platelets- lifespan -Clot retraction-disorders.pptx
 
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
Earliest Galaxies in the JADES Origins Field: Luminosity Function and Cosmic ...
 
RNA INTERFERENCE: UNRAVELING GENETIC SILENCING
RNA INTERFERENCE: UNRAVELING GENETIC SILENCINGRNA INTERFERENCE: UNRAVELING GENETIC SILENCING
RNA INTERFERENCE: UNRAVELING GENETIC SILENCING
 
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
Astronomy Update- Curiosity’s exploration of Mars _ Local Briefs _ leadertele...
 
insect taxonomy importance systematics and classification
insect taxonomy importance systematics and classificationinsect taxonomy importance systematics and classification
insect taxonomy importance systematics and classification
 
extra-chromosomal-inheritance[1].pptx.pdfpdf
extra-chromosomal-inheritance[1].pptx.pdfpdfextra-chromosomal-inheritance[1].pptx.pdfpdf
extra-chromosomal-inheritance[1].pptx.pdfpdf
 
erythropoiesis-I_mechanism& clinical significance.pptx
erythropoiesis-I_mechanism& clinical significance.pptxerythropoiesis-I_mechanism& clinical significance.pptx
erythropoiesis-I_mechanism& clinical significance.pptx
 
Seminar of U.V. Spectroscopy by SAMIR PANDA
 Seminar of U.V. Spectroscopy by SAMIR PANDA Seminar of U.V. Spectroscopy by SAMIR PANDA
Seminar of U.V. Spectroscopy by SAMIR PANDA
 
Hemoglobin metabolism_pathophysiology.pptx
Hemoglobin metabolism_pathophysiology.pptxHemoglobin metabolism_pathophysiology.pptx
Hemoglobin metabolism_pathophysiology.pptx
 
GBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram StainingGBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram Staining
 

Beckmann rearrangement ppt

  • 1. Beckmann Rearrangement Persented by Dinesh yadav 2017PCY5358 1 Submitted to:- Dr. Ragini Gupta Prof.&HOD Dept. of Chemistry
  • 2. Beckmann rearrangement • The acid-catalysed conversion of ketoximes to amides is known as the Beckmann rearrangement • The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923) • This rearrangement is occurs in both cyclic and acyclic compounds . • Aldoximes are less reactive. • Cyclic oximes yield lactams and acyclic oximes yield amides 2J. Am. Chem. Soc., 1924, 46 (6), pp 1477–1483 DOI: 10.1021/ja01671a018
  • 3. Beckmann rearrangement 3 Reagents:- Conc.H2SO4, HCl, PCl5, PCl3, SOCl2, ZnO, SiO2, PPA (Poly phosphoric acid) etc., are commonly employed in Beckmann rearrangement. Oxime Amide J. Am. Chem. Soc., 1924, 46 (6), pp 1477–1483 DOI: 10.1021/ja01671a018
  • 4. Reaction mechanism The first step in the process is formation of an oxime from the aldehyde or ketone, 4
  • 5. Reaction mechanism 5 This rearrangement take place an alkyl migration with expulsion of the hydroxyl group to form a nitrilium ion followed by hydrolysis.
  • 6. Migratory aptitude • The relative migratory aptitudes of different groups in Beckmann rearrangement is illustrated below. 6
  • 7. Applications in drug synthesis:- • An alternative industrial synthesis method for Paracetamol. It is involves direct acylation of phenol with acetic anhydride catalyzed by HF, conversion of the ketone to a ketoxime with hydroxylamine, followed by the acid-catalyzed Beckmann rearrangement to give the amide 7 Paracetamol
  • 8. Applications in drug synthesis:- • The Beckmann rearrangement is also used in the synthesis of 1. DHEA 2. Benazepril 3. Etazepine etc. 8
  • 9. Applications in polymer synthesis:- • Beckmann rearrangement can be rendered catalytic using cyanuric chloride and zinc chloride as a co-catalyst. For example, cyclododecanone can be converted to the corresponding lactam, the monomer used in the production of Nylon 12 9
  • 10. Applications in polymer synthesis:- • The Beckmann rearrangement is also used in the synthesis of Nylon 6 10