This slide discusses about fused heterocyclic compound Acridine..the structural analogue of anthracene with one carbon group is replaced with nitrogen atom.
This slide discusses about fused heterocyclic compound Acridine..the structural analogue of anthracene with one carbon group is replaced with nitrogen atom.
THIS SLIDE HAVE GOOD CONTENT. THIS SLIDE CONTAIN INTRODUCTION, STRUCTURE, RESONANCE, AROMATICITY, PHYSICAL AND CHEMICAL PROPERTIES, SYNTHESIS AND APPLICATION OF QUINOLINE.
Unit iii heterocyclic compounds as per PCI Syllabus of POC-IIIGanesh Mote
Nomenclature of hetero cyclic compounds, classification of heterocyclic compounds, Reactivity, aromaticity, orbital picture, stability, resonance energy, resonance structure, basicity, method of preparation, reaction and medicinal uses of Pyrrole, furan and thiophene
THIS SLIDE HAVE GOOD CONTENT. THIS SLIDE CONTAIN INTRODUCTION, STRUCTURE, RESONANCE, AROMATICITY, PHYSICAL AND CHEMICAL PROPERTIES, SYNTHESIS AND APPLICATION OF QUINOLINE.
Unit iii heterocyclic compounds as per PCI Syllabus of POC-IIIGanesh Mote
Nomenclature of hetero cyclic compounds, classification of heterocyclic compounds, Reactivity, aromaticity, orbital picture, stability, resonance energy, resonance structure, basicity, method of preparation, reaction and medicinal uses of Pyrrole, furan and thiophene
B.phram
Semester .4
Subject : Organic chemistry - III
Use as reference and also usable for examination prearation.
gtu afflitited phramacy college's student may using this ppt.
Unit II-Geometric isomerism and conformational isomer as PCI Syllabus of POC-IIIGanesh Mote
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Unit i.Optical Isomerism as per PCI syllabus of POC-III Ganesh Mote
Unit I optical isomerism which is included in PCI syllabus of Sem IV of POC-III subject
This Unit Includes all points of Unit I such as nomenclature, R& S, d&l, D& L isomerism, Meso compounds, diastereomers, chirality, resolution of racemic mixture, enantiomers, Asymmetric synthesis,
Benzene and its derivatives- According to PCI Syllabus Ganesh Mote
Benzene history, nomenclature, orbital structure, resonance structure, kekule structure,synthetic evidences, structural and analytical evidences, Directive effect of benzene, structure and uses of DDT, BHC, saccharine
Definition, Classification, Basicity, Effect of substituents on basicity of amines, Preparation, reaction, Identification test, Structure and Uses of amines
Preparation, reactions, Acidity, effect of substituents on acidity, structure and uses of carboxylic acid and identification tests for carboxylic acid, amide and ester
Preparation and reaction of aldehyde and ketone, electromeric effect, aldol condensation, cannizarro reaction, perkin condensation, benzoin condensation, nucleophilic addition reaction and uses of aldehyde and ketone
Classification, Nomenclature and structural isomerism of organic compound Ganesh Mote
Classification of organic compound, Nomenclature of alkane, alkene, alkyne, alcohol, alkyl halide, aldehyde, ketone, carboxylic acid and its derivatives, amines, ethers, polyfunctional groups and structural isomerism of organic compounds
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Francesca Gottschalk from the OECD’s Centre for Educational Research and Innovation presents at the Ask an Expert Webinar: How can education support child empowerment?
The French Revolution, which began in 1789, was a period of radical social and political upheaval in France. It marked the decline of absolute monarchies, the rise of secular and democratic republics, and the eventual rise of Napoleon Bonaparte. This revolutionary period is crucial in understanding the transition from feudalism to modernity in Europe.
For more information, visit-www.vavaclasses.com
The Roman Empire A Historical Colossus.pdfkaushalkr1407
The Roman Empire, a vast and enduring power, stands as one of history's most remarkable civilizations, leaving an indelible imprint on the world. It emerged from the Roman Republic, transitioning into an imperial powerhouse under the leadership of Augustus Caesar in 27 BCE. This transformation marked the beginning of an era defined by unprecedented territorial expansion, architectural marvels, and profound cultural influence.
The empire's roots lie in the city of Rome, founded, according to legend, by Romulus in 753 BCE. Over centuries, Rome evolved from a small settlement to a formidable republic, characterized by a complex political system with elected officials and checks on power. However, internal strife, class conflicts, and military ambitions paved the way for the end of the Republic. Julius Caesar’s dictatorship and subsequent assassination in 44 BCE created a power vacuum, leading to a civil war. Octavian, later Augustus, emerged victorious, heralding the Roman Empire’s birth.
Under Augustus, the empire experienced the Pax Romana, a 200-year period of relative peace and stability. Augustus reformed the military, established efficient administrative systems, and initiated grand construction projects. The empire's borders expanded, encompassing territories from Britain to Egypt and from Spain to the Euphrates. Roman legions, renowned for their discipline and engineering prowess, secured and maintained these vast territories, building roads, fortifications, and cities that facilitated control and integration.
The Roman Empire’s society was hierarchical, with a rigid class system. At the top were the patricians, wealthy elites who held significant political power. Below them were the plebeians, free citizens with limited political influence, and the vast numbers of slaves who formed the backbone of the economy. The family unit was central, governed by the paterfamilias, the male head who held absolute authority.
Culturally, the Romans were eclectic, absorbing and adapting elements from the civilizations they encountered, particularly the Greeks. Roman art, literature, and philosophy reflected this synthesis, creating a rich cultural tapestry. Latin, the Roman language, became the lingua franca of the Western world, influencing numerous modern languages.
Roman architecture and engineering achievements were monumental. They perfected the arch, vault, and dome, constructing enduring structures like the Colosseum, Pantheon, and aqueducts. These engineering marvels not only showcased Roman ingenuity but also served practical purposes, from public entertainment to water supply.
Instructions for Submissions thorugh G- Classroom.pptxJheel Barad
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Operation “Blue Star” is the only event in the history of Independent India where the state went into war with its own people. Even after about 40 years it is not clear if it was culmination of states anger over people of the region, a political game of power or start of dictatorial chapter in the democratic setup.
The people of Punjab felt alienated from main stream due to denial of their just demands during a long democratic struggle since independence. As it happen all over the word, it led to militant struggle with great loss of lives of military, police and civilian personnel. Killing of Indira Gandhi and massacre of innocent Sikhs in Delhi and other India cities was also associated with this movement.
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This Gasta posits a strategic approach to integrating AI into HEIs to prepare staff, students and the curriculum for an evolving world and workplace. We will highlight the advantages of working with these technologies beyond the realm of teaching, learning and assessment by considering prompt engineering skills, industry impact, curriculum changes, and the need for staff upskilling. In contrast, not engaging strategically with Generative AI poses risks, including falling behind peers, missed opportunities and failing to ensure our graduates remain employable. The rapid evolution of AI technologies necessitates a proactive and strategic approach if we are to remain relevant.
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http://sandymillin.wordpress.com/iateflwebinar2024
Published classroom materials form the basis of syllabuses, drive teacher professional development, and have a potentially huge influence on learners, teachers and education systems. All teachers also create their own materials, whether a few sentences on a blackboard, a highly-structured fully-realised online course, or anything in between. Despite this, the knowledge and skills needed to create effective language learning materials are rarely part of teacher training, and are mostly learnt by trial and error.
Knowledge and skills frameworks, generally called competency frameworks, for ELT teachers, trainers and managers have existed for a few years now. However, until I created one for my MA dissertation, there wasn’t one drawing together what we need to know and do to be able to effectively produce language learning materials.
This webinar will introduce you to my framework, highlighting the key competencies I identified from my research. It will also show how anybody involved in language teaching (any language, not just English!), teacher training, managing schools or developing language learning materials can benefit from using the framework.
3. Metal hydride reduction (NaBH4 and LiAlH4)
The most common sources of the hydride Nucleophile are lithium aluminum hydride
(LiAlH4) and sodium borohydride (NaBH4).
The hydride anion is not present during this reaction; rather, these reagents serve as a
source of hydride due to the presence of a polar metal-hydrogen bond
Because aluminium is less electronegative than boron, the Al-H bond in LiAlH4 is
more polar, thereby, making LiAlH4 a stronger reducing agent.
Addition of a hydride anion (H:-) to an aldehyde or ketone gives an alkoxide anion,
which on protonation yields the corresponding alcohol .
Aldehydes produce 1°-alcohols and ketones produce 2°-alcohols.
Al
H
H H
H
Li B
H
H H
H
Na H
4. Metal hydride reduction by LiAlH4 and NaBH4
R C
O
H
LiAlH4
R C
H
OH
H LiOH
+ + AlH3
R C
O
H
NaBH4
R C
H
OH
H NaCl
+ + BH3
HCl
H2O
5. Mechanism of Metal hydride reduction by LiAlH4
R C
O
H + Al
H
H
H
H
Li R C
O
H
H
Li+
+ AlH3
1. Nucleophilic attack by hydride
2.Protonation of Alkoxide ion
R C
O
H
H
Li+
+ H OH R C
OH
H
H
+ LiOH
6. Mechanism of Metal hydride reduction by NaBH4
R C
O
H + B
H
H
H
H
Na R C
O
H
H
Na+
+ BH3
1. Nucleophilic attack by hydride
2.Protonation of Alkoxide ion
R C
O
H
H
Na+
+ H Cl R C
OH
H
H
+ NaCl
7. Examples of Metal hydride reduction by LiAlH4&bNaBH4
H3C C
O
H
LiAlH4
H3C C
H
OH
H LiOH
+ + AlH3
H3C C
O
H
NaBH4
H3C C
H
OH
H NaCl
+ + BH3
HCl
H2O
acetaldehyde
acetaldehyde ethanol
ethanol
H3C C
O
CH3
LiAlH4
H3C C
H
OH
LiOH + AlH3
H3C C
O
CH3
NaBH4
H3C C
H
OH
CH3 NaCl + BH3
HCl
H2O
Acetone
acetone
CH3
+
+
propan-2-ol
propan-2-ol
8. Application
1. Aldehydes are converted into primary alcohol(Alcohol preparation)
2. Ketones are converted into secondary alcohol (Alcohol Preparation)
3. Identification Class of alcohol
10. INTRODUCTION
This reaction was first reported by Clemmensen of Park Davis in 1913.
It is the reduction of carbonyl groups ( in aldehyde and ketone) to
methylene group.
This reaction done with zinc amalgam and hydrochloric acid and it is
generally known as Clemmensen reduction.
The Clemmensen reduction is particularly effective at reducing aryl- alkyl
ketones,such as those formed in a Friedel-Crafts acylation.
4
14. APPLICATIONS
🠶
This reaction has widely used to convert a carbonyl group into a
methylene group.
🠶
Also important application in the preparation of polycyclic
aromatics and aromatics containing unbranched side hydrocarbon
chains.
🠶
To reduce aliphatic and mixed aliphatic-aromatic carbonyl
compounds
8
16. Birch Reduction
The reduction of aromatic substrates with alkali metals, alcohol in liquid
ammonia is known as "Birch reduction
This reaction is named after a Australian chemist Sir Arthur John Birch.
The Birch reduction is an organic reaction where aromatic rings undergo a
1,4-reduction to provide unconjugated cyclohexadienes .
The reduction is conducted by sodium or lithium metal in liquid ammonia
and in the presence of an alcohol.
17. Birch Reduction
The mechanism begins with a Single Electron Transfer (SET) from the
metal to the aromatic ring, forming a radical anion.
The anion then picks up a proton from the alcohol which results in a neutral
radical intermediate.
Another SET, and abstraction of a proton from the alcohol results in the
final cyclohexadiene product and two equivalents of metal alkoxide salt as a
by-product.
19. Mechanism of Birch Reduction
Na NH3 2Na+ 2e-
e-
H
H
H
H
HO CH3
2
H
H
H
e-
H
H
H
HO CH3
H
H
H
H
-CH3O
-CH3O
CH3 O + 2Na
2 2CH3ONa
20. Application of Birch Reduction
1) Naphthalene can be reduced to 1,4,5,8-tetrahydronaphthalene by
using Birch reduction conditions.
Na, NH3(Liq)-78
°C
EtOH, Et2O
1,4,5,8-tetrahydronaphthalene
2) In the birch reduction of benzoic acid, the protonation occurs at ipso and para positions
relative to -COOH group on the benzene ring.
COOH
Na, NH3
C2H5OH
COOH
cyclohexa-2,5-dienecarboxylic acid
benzoic acid
22. INTRODUCTION
The Wolff– Kishner reduction was discovered independently by N. Kishner
in 1911 and L. Wolff in 1912.
TheWolff–Kishner reduction is a reaction used in organic chemistry to convert
carbonyl functionalities into methylene groups.
The Wolff-Kishner reduction is an organic reaction used to convert an
aldehyde or ketone to an alkane using hydrazine, base, and thermal
conditions
Because the Wolff–Kishner reduction requires highly basic conditions, it is
unsuitable for base-sensitive substrates.
26. MODIFICATION
🠶
The reaction has been extensively modified.
🠶
One of the modification uses the Huang Minlon modification using
distillation to remove excess water and also used 85% hydrazine and
solvent used is ethylene glycol.
🠶
In addition, the Wolff- kishner reduction has been carried out in
DMSO instead of hydroxylic solvent by addition of hydrazones into
anhydrous DMSO containing freshly sublimed potassium tert-
butoxide at 250C.
🠶
Moreover,it has been reported that the Wolff-Kishner reduction can
occur in a very short period of time in a microwave irradiation,
affording product with high purity.
13
27. APPLICATIONS
🠶
This reaction has very broad application in organic synthesis,
especially for the multiwalled carbon nanotubes.
🠶In 2011, Pettus and Green reduced a tricyclic carbonyl compound
using the Huang Minlon modification of the Wolff–Kishner
reduction.Several attempts towards decarbonylation of tricyclic
allylic acetate containing ketone failed and the acetate functionality
had to be removed to allow successful Wolff–Kishner reduction.
Finally, the allylic alcohol was installed via oxyplumbation.
🠶
The Wolff–Kishner reduction has also been used on kilogram scale
for the synthesis of a functionalized imidazole substrate.
14
29. INTRODUCTION
Named after Rupert Viktor Oppenauer.
It is a gentle method for selectively oxidizing secondary alcohols to
ketones.
The reaction is the opposite of Meerwein– Ponndorf –Verley
reduction.
The alcohol is oxidized with aluminium isopropoxide in excess acetone.
This shifts the equilibrium toward the product side.
30. The oxidation is highly selective for secondary alcohols and does not
oxidize other sensitive functional groups such as amines and sulfides,
Though primary alcohols can be oxidized under Oppenauer conditions,
primary alcohols are seldom oxidized by this method due to the
competing aldol condensation of aldehyde products.
The Oppenauer oxidation is still used for the oxidation of acid labile
substrates.
Cont……
33. MODIFICATION
Woodward modification
🠶In the Woodward modification, Woodward substituted potassium tert-
butoxide for the aluminium alkoxide.
🠶The Woodward modification of the Oppenauer oxidation is used
when certain alcohol groups do not oxidize under the standard
Oppenauer reaction conditions.
🠶For example, Woodward used potassium tert-butoxide
and benzophenone for the oxidation of quinine to quininone, as the
traditional aluminium catalytic system failed to oxidize quinine due
to the complex formed by coordination of the Lewis-
basic nitrogen to the aluminium centre.
28
34. Cont……
Other modifications
• Several modified aluminium alkoxide catalysts have been also reported
• For example, a highly active aluminium catalyst was reported by Maruoka and
co-workers which was utilized in the oxidation of carveol to carvone (a member
of a family of chemicals called terpenoids) in excellent yield (94%)
29
36. APPLICATIONS
The Oppenauer oxidation is used to prepare analgesics in the pharmaceutical
industry such as morphine and codeine. For instance, codeinone is prepared
by the Oppenauer oxidation of codeine.
37. Cont……
The Oppenauer oxidation is also used to synthesize hormones.
Progesterone is prepared by the Oppenauer oxidation of
pregnenolone.
39. 6. Dakin Reaction
Dakin Reaction is the replacement of the aldehyde group of ortho and para hydroxy and
ortho amino-benzaldehyde (or ketone) by a hydroxyl group on reaction with alkaline
hydrogen peroxide.
H2O2
NaOH
OH
C
O
H
OH
OH
+ H-COOH
Catechol
Salicylic acid
40. 6. Dakin Reaction- Mechanism
NaOH OH + Na HO OH
OH-
H2O
OH
C
O
H
HO O
O OH
OH
C
O
H
O OH
Na
-NaOH
OH
O
C
O
H
H-OH
OH
OH
Catechol
+ HCOOH
salicylic acid
1 2.
3.
41. Applications of Dakin oxidation reaction
1. Synthesis of Pyrro gallol mono methyl ether- Anesthetic agent
2. Synthesis of Hydroquinone-Treatment of acne
3. Phenol preparation
CHO
OH
OCH3
H2O2
NaOH, H2O
OH
OH
OCH3
2,3 Dihydroxy anisole
(Pyrrogallol monomethyl ether)
C OH
CH3
O
H2O2
NaOH, H2O
HO OH
p-hydroxyacetophenone Hydroquinone
-2-hydroxy, 3-3methoxy
benzaldehyde
42. 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
2
45. Reaction mechanism
This rearrangement take place an alkyl migration with expulsion of the hydroxyl
group to form a nitrilium ion followed by hydrolysis.
4
5
46. Migratory aptitude
• The relative migratory aptitudes of different groups in Beckmann rearrangement
is illustrated below.
4
6
47. 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
48. 48
Applications in drug synthesis:-
• The Beckmann rearrangement is also used in the synthesis
of
1. DHEA
2. Benazepril
3. Etazepine etc.
49. 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
49
50. Applications in polymer synthesis:-
• The Beckmann rearrangement is also used in the
synthesis of Nylon 6
50
51. Schmidt Rearrangement
The Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or
carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
The reaction is superior to the Curtius or Hofmann rearrangement because it directly converts an acid or ester to amine, without
making the acid derivatives.
The reaction is limited to acid insensitive compounds.
The reaction is effective with carboxylic acids to give amines, and with ketones to give amides.
53. The reaction proceeds with faster rate with sterically hindered acids which forms acyl cation in presence of acids, even
without heating.
Crowding around the a-center of the “R” group facilitates the formation of acyl cation, thus enhances the rate.
Acids that do not form acyl cation react through the protonation of the acid under heating, as shown previously.
acyl cation
56. Formation of the carbocation step (6) in Schmidt reaction can be evidenced by the formation of the tetrazole (A) and the
substituted urea (B), which are often isolated from the reaction medium when excess of azide is used. These products are
obtained from the intermediate carbocation as the amide does not react with hydrogen azide in the reaction condition.
(A)
(B)
(6)
Evidence for the carbocation intermediate formation
Unsymmetrical ketone gives a mixture of two product
57. Application of Schmidt Rearrangement
1. Preparation of Primary Amines
COOH
H3C +NH3
H2SO4
NH2
H3C
Toludine
Tolueic acid
2. Preparation of Capro-lactams and polymerisation of caprolactam with base to form nylone
O
+ NH3
H2SO4
NH
O
Lactam
Cyclohexanone
58. Application of Schmidt Rearrangement
3. Synthesis of Acetanilide from acetophenone- Analgesic, Antirhuematic
4. Synthesis of Benzanilide from Benzophenone- Perfume and dye
C
O
CH3
+ NH3
H2SO4
acetophenone
NH C
O
CH3
Acetanilide
C
O
+ NH3
H2SO4
NH C
O
benzophenone
Benzanilide
59. Claisen–Schmidt Condensation Reaction
The reaction between an aldehyde or ketone having an alpha-hydrogen with an
aromatic carbonyl compound lacking an alpha hydrogen is called the Claisen–
Schmidt condensation.
In cases where the product formed still has reactive alpha hydrogen and a hydroxide
adjacent to an aromatic ring, the reaction will quickly undergo dehydration leading to the
condensation product
C
O
H
+ CH3
C
O
CH3
NaOH, Aq. EtOH
H
C CH
C
O
C
H
H
C
Dibenzal acetone
Benzaldehyde
2
62. Application
1. A reaction employed for preparation of unsaturated aldehydes and ketones
by condensation of aromatic aldehydes with aliphatic aldehyde or ketone in presence of
sodium hydroxide. E.g. synthesis of cinnamaldehyde which is used in perfumery industry
C
O
H
+ CH3 C
O
H
H
C
H
C C
O
H
10% NaOH
Cinnamaldehyde
Bezaldehyde
2. Synthesis of Dibenzalacetone which is used as sun protecting agent in sun screen lotion
C
O
H
+ CH3
C
O
CH3
NaOH, Aq. EtOH
H
C CH
C
O
C
H
H
C
Dibenzal acetone
Benzaldehyde
2
63. Application
3. Synthesis of Chacone
4. This reaction also used to synthesis of natural products such as ionone, Flavonone,
piperine etc
C
O
CH3
+ H C
O
C
H
C CH
10% NaOH
Chalcones
Acetophenone
O
Benzaldehyde
ethanol