The document summarizes various oxidation reactions and their mechanisms and applications. It discusses Dakin oxidation, Oppenauer oxidation, Moffatt oxidation, Parikh-Doering oxidation, Jones oxidation, Corey-Kim oxidation, Wacker-Tsuji oxidation, Criegee oxidation, Hass-Bender oxidation, and Lindgren-Pinnick oxidation. These reactions allow the conversion of alcohols to carbonyl compounds like aldehydes and ketones, and in some cases carboxylic acids, using oxidizing agents such as hydrogen peroxide, DMSO, chromic acid, NCS, and sodium chlorite. The summarized reactions find applications in organic synthesis and production of pharmaceuticals, flavors,
N-BROMOSUCCINAMIDE A REAGENT USED IN THE SYNTHESIS, IT IS ALSO A SYNTETIC REAGENT AND HERE IN THIS PRESENTATION THE MOLECULAR FORMULA ITS ALTERNATE NAME APLLICATION ARE DISCUSSED.
N-BROMOSUCCINAMIDE A REAGENT USED IN THE SYNTHESIS, IT IS ALSO A SYNTETIC REAGENT AND HERE IN THIS PRESENTATION THE MOLECULAR FORMULA ITS ALTERNATE NAME APLLICATION ARE DISCUSSED.
Rearrangement to Electron Deficient Carbon
Rearrangement to Electron Deficient Nitrogen
Rearrangement to Electron Deficient Oxygen
Rearrangement to Electron-Rich Carbon
Aromatic Rearrangements
molecular rearrangement introduction which includes nucleophilic, electrophilic, and free radical rearrangement. and mechanism, applications of favorskki and benzil benzilic acid rearrangement.
The [2,3]-Wittig rearrangement is a special class of [2,3]-sigma tropic rearrangement which involves an α-oxy carbanions as the migrating terminus to afford various types of homoallylic alcohols.
SMILES REARRANGEMENT [REACTION AND MECHANISM]Shikha Popali
THE SMILES REARRANGMENT IS THE PROCESS OF REARRANGING OF ELEMENTS OF THE STRUCTURE, WHERE IN THIS PRESENTATION HOW TO REARRANGE IS EXPLAIN WITH ITS MECHANISM
An organic species which has a carbon atom bearing only six electrons in its outermost shell and has a positive charge is called carbocation.
The positively charged carbon of carbocation is sp2 hybridized.
The unhybridized p-orbital remains vacant.
They are highly reactive and act as reaction intermediate.
They are also called carbonium ion.
Rearrangement to Electron Deficient Carbon
Rearrangement to Electron Deficient Nitrogen
Rearrangement to Electron Deficient Oxygen
Rearrangement to Electron-Rich Carbon
Aromatic Rearrangements
molecular rearrangement introduction which includes nucleophilic, electrophilic, and free radical rearrangement. and mechanism, applications of favorskki and benzil benzilic acid rearrangement.
The [2,3]-Wittig rearrangement is a special class of [2,3]-sigma tropic rearrangement which involves an α-oxy carbanions as the migrating terminus to afford various types of homoallylic alcohols.
SMILES REARRANGEMENT [REACTION AND MECHANISM]Shikha Popali
THE SMILES REARRANGMENT IS THE PROCESS OF REARRANGING OF ELEMENTS OF THE STRUCTURE, WHERE IN THIS PRESENTATION HOW TO REARRANGE IS EXPLAIN WITH ITS MECHANISM
An organic species which has a carbon atom bearing only six electrons in its outermost shell and has a positive charge is called carbocation.
The positively charged carbon of carbocation is sp2 hybridized.
The unhybridized p-orbital remains vacant.
They are highly reactive and act as reaction intermediate.
They are also called carbonium ion.
Environmental Catalysis Module: Students examines different types of catalytic systems, including heterogeneous and homogeneous catalysis. Depending on the knowledge they gained during activities, the students are then asked to design their projects.
Our Project: Methanol Synthesizer Catalyst : A catalyst composed of copper alloys with ceria (cerium-oxide) nanoparticles, sometimes also mixed with titania. The catalyst were exposed to pressure of 0.5 atom of CO2 and 4.5 atom of H2 at a range of reaction temperatures 500-600 Kalvin.
By: ABJ_ Cobalt8, Ali Bin Jassim Secondary Independent School for Boys.
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.
Presented by Dhanashree Kavhale. M. Pharm.(Pharmaceutical Chemistry) 1st year.
Various organic named reactions are there in Advanced Organic Chemistry I, as some of them are explained along with their mechanism.
Diel's-Alder and Gattermann Koch ReactionsPRUTHVIRAJ K
n organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism
Another client, Ms. Dunham, has asked you to help her understand h.docxjustine1simpson78276
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Be clear in our elaboration s that Ms. Dunham, a person with no business or tax background, can understand.
Kinetics of the Hydrolysis of
Atmospherically Relevant
Isoprene-Derived Hydroxy Epoxides
N E I L C . C O L E - F I L I P I A K ,
A L I S O N E . O ’ C O N N O R , A N D
M A T T H E W J . E L R O D *
Department of Chemistry and Biochemistry, 119 Woodland
Street, Oberlin College, Oberlin, Ohio 44074
Received June 4, 2010. Revised manuscript received July
16, 2010. Accepted July 19, 2010.
Isoprene (the most abundant nonmethane hydrocarbon
emitted into the atmosphere) is known to undergo oxidation to
2-methyl-1,2,3,4-butanetetraol, a hydrophilic compound
present in secondary organic aerosol (SOA) in the atmosphere.
Recent laboratory work has shown that gas phase hydroxy
epoxides are produced in the low NOx photooxidation of isoprene
and that these epoxides are likely to undergo efficient acid-
catalyzed hydrolysis on SOA to 2-methyl-1,2,3,4-butanetetraol at
typical SOA acidities. In order to confirm this hypothesis, the
specific hydroxy epoxides observed in the isoprene photooxidation
experiment (as well as several other related species) were
synthesized, and the hydrolysis kinetics of all species were
studied via nuclear magnetic resonance (NMR) techniques. It
was determined that the isoprene-derived hydroxy epoxides
should undergo efficient hydrolysis under atmospheric conditions,
particular on lower pH SOA. An empirical structure-reactivity
model was constructed that parametrized the hydrolysis
rate constants according to the carbon substitution pattern on
the epoxide ring and number of neighboring hydroxy functional
groups. Compared to the previously studied similar nonfunc-
tionalized epoxides, the presence of a hydroxy group at the R
position to the epoxy group was found to reduce the hydrolysis
rate constant by a factor of 20, and the presence of a hydroxy
group at the beta position to the epoxy group was found to
reduce the hydrolysis rate constant by a factor of 6.
Introduction
Because secondary organic aerosol (SOA) is known to play
a critical role in issues such as air pollution (1) and climate
change (2), there continues to be intense interest in the
formation mechanisms for these particles. Isoprene,
the dominant non-methane hydrocarbon emitted into the
atmosphere (3), has only recently been implicated in SOA
formation. In 2004, Claeys et al. identified 2-methyl-1,2,3,4-
butanetetraol in SOA found in air samples from the Amazon
and inferred that it must be an oxidation product of isoprene
(4). Several laboratory an.
Formulation and operation of a Nickel based methanation catalystSakib Shahriar
The objective of this experiment was to get a firsthand experience of the preparation of a catalyst for methanation reaction and to evaluate the performance of the catalyst in a fixed bed tubular reactor. In the first part of the experiment a nickel-based catalyst was synthesized. The catalyst will have nickel as the active component and alumina as the support. the catalyst precursor was prepared by co-precipitation from a solution of nitrate salts of nickel and aluminum. The precipitate was filtered out, washed, dried and calcined to obtain the catalyst. In the second part, the catalyst was activated and performance analysis was done alone with loaded in a fixed bed reactor. The percentage conversion of CO to CH4 was 96.38% and the selectivity of CH4 production to CO2 production was 3.348.
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
How to Create Map Views in the Odoo 17 ERPCeline George
The map views are useful for providing a geographical representation of data. They allow users to visualize and analyze the data in a more intuitive manner.
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.
Synthetic Fiber Construction in lab .pptxPavel ( NSTU)
Synthetic fiber production is a fascinating and complex field that blends chemistry, engineering, and environmental science. By understanding these aspects, students can gain a comprehensive view of synthetic fiber production, its impact on society and the environment, and the potential for future innovations. Synthetic fibers play a crucial role in modern society, impacting various aspects of daily life, industry, and the environment. ynthetic fibers are integral to modern life, offering a range of benefits from cost-effectiveness and versatility to innovative applications and performance characteristics. While they pose environmental challenges, ongoing research and development aim to create more sustainable and eco-friendly alternatives. Understanding the importance of synthetic fibers helps in appreciating their role in the economy, industry, and daily life, while also emphasizing the need for sustainable practices and innovation.
1. Oxidation Reactions
Presented By:-
Ganesh Dashrath Ahire
Reg. No- 20MCM3133
M.S. (Pharm) 1st Year (2nd Semester)
Department of Medicinal Chemistry
National Institute of Pharmaceutical Education and Research (NIPER),
S.A.S. Nagar, Mohali, Punjab, India
1
LS-610 Credit Seminar
2. Introduction
1. Oxidation
- Oxidation is loss of electrons during a reaction by a molecule or atom
- Oxidation is gain of oxygen and loss of hydrogen by molecule
2. Oxidizing agent / Oxidant
- Agent which accepts or receives electron from another substance and get reduced
- It causes another substance to be oxidized.
2
3. 1. Dakin Oxidation
- Oxidation reaction in which ortho/para hydroxylated phenyl aldehyde converted to
benzenediol and carboxylate.
- Oxidizing agent – Hydrogen peroxide
General Reaction scheme
Oxidation Reaction and oxidizing agents
3
4. Mechanism of Dakin oxidation reaction
Steps involved
1. Nucleophile addition of hydroperoxide
anion to carbonyl carbon
2. [1,2]-aryl migration and hydroxide
elimination
3. Nucleophilic addition of hydroxide ion to
ester carbonyl carbon
4. Elimination of phenoxide ion
4
5. Application of Dakin oxidation reaction
1. Synthesis of benzenediols e.g., catechol
2. Synthesis of guaiacol which is precursor in the synthesis of several flavorants
3. Synthesis of hydroquinone which is a common photograph-developing agent
4. Synthesis of indolequinones which is natural originating compound with anti-biotic,
anti-fungal and anti-tumor property
5
6. 2. Oppenauer Oxidation
General Reaction scheme
- Selective oxidation of 2o alcohols
- reaction in which conversion of secondary alcohols to ketone
- Oxidizing agent - Aluminum isopropoxide
6
7. Mechanism of Oppenauer oxidation reaction
Steps involved
1. Complex formation between alcohol and
aluminum
2. Deprotonation of complex
3. Formation of six membered transition state
4. Hydride transfer from alpha carbon of alcohol to
the carbonyl of acetone
7
8. Applications of Oppenauer Oxidation reaction
1. In the preparation of Codeinone from codeine
2. Synthesis of hormones such as progesterone from pregnenolone
3. Synthesis of lactones from 1,4 and 1,5 diols
Chem. Rev. 2006, 106, 2943–89
ChemPlusChem. 1976, 41: 1056–1065 8
10. 4. Moffatt Oxidation
General Reaction scheme
- Reaction in which 1o or 2o alcohol converted to aldehyde or ketone
- Oxidizing agent – DMSO and DCC
10
11. Mechanism of Moffatt oxidation reaction
Steps involved
1. Attack of DMSO to the DCC
2. Again Protonation of DCC
3. Addition of alcohol oxygen on the sulphur atom
4. Decomposition of sulfenate intermediate and
elimination of 1,3-dicyclohexylurea
11
12. J.Med.Chem. 1997, 41, 1056–1065
Applications of Moffatt oxidation reaction
1. Moffatt oxidation provides metal free pathway to oxidize 1o or 2o alcohol to aldehyde
or ketone
2. Conversion of protected nucleosides to 5’- carboxaldehyde analogue
12
13. 5. Parikh-Doering oxidation
General Reaction scheme
- Reaction in which 1o or 2o alcohol converted to aldehyde or ketone
- Oxidizing agent – DMSO
- DMSO is activated by Sulfur trioxide and pyridine complex
- Reaction proceeds in presence of base
1. Used in Nicolaou cortistatin total synthesis. Cortistatin is anti-
inflammatory peptide
Applications of Parikh-Doering oxidation
J. Am. Chem. Soc. 2009, 131, 10587-10597 13
14. Mechanism of Parikh-Doering oxidation reaction
Steps involved
1. Reaction between DMSO and sulfur trioxide
2. Nucleophilic attack by alcohol and deprotonation by
pyridine
3. Deprotonation by base
14
15. 6. Jones Oxidation
General Reaction scheme
- Reaction in which 1o or 2o alcohol converted to carboxylic acid and ketone
- Oxidizing agent – Chromic trioxide and sulfuric acid
15
16. Mechanism of Jones oxidation reaction
Steps involved
1. Formation of chromic acid in situ
2. Formation of chromate ester
3. Intramolecular arrangement in presence
of base 16
17. Applications of Jones oxidation reaction
1. Jones reagent was used in breath analyzers. Jones reagent oxidizes ethanol to acetic acid and itself get
reduced. Reduced reagent is greenish brown in color. More the reagent reduced to green color more
wasted the person.
2. oxidation of secondary alcohols to ketones
3. Oxidation of primary alcohols to carboxylic acids
17
18. 7. Corey Kim Oxidation
General Reaction scheme
- Reaction in which 1o or 2o alcohol converted to aldehyde or ketone
- Oxidizing agent - N-Chlorosuccinimide
18
19. Mechanism of Corey-Kim oxidation reaction
Steps involved –
1. NCS and Dimethyl sulfide reacts and forms active
species
2. Nucleophilic addition of alcohol oxygen to electrophilic
sulfur
3. Deprotonation of sulfenate intermediate by base
4. Hydride transfer from alcohol to carbon
19
20. Applications of Corey-Kim Oxidation reaction
1. Corey-Kim oxidation protocol employed in the synthesis of novel bicyclic macrolide drug
candidate EDP-420
2. Cook et al. implemented successful synthesis of indole alkaloids such as polyneuridine,
macusine which showing different biological activity. They used Corey-Kim oxidation in
their reaction pathway
Monatsh chem. 2016, 147, 961-987 20
21. 8. Wacker-Tsuji Oxidation
General Reaction scheme
1. Wacker oxidation reaction concerns about ethene to ethanal
2. Wacker-Tsuji reaction is lab scale modification to generate ketones
3. Oxidizing agent – Palladium in presence of oxygen
4. Redox cocatalyst- copper
1. Wacker oxidation used in the synthesis of macrolide Elaiolide
2. Synthesis of Hennoxazole A
Applications of Wacker-Tsuji Oxidation
Tetrahedron. 2008, 64, 4718
Tetrahedron. 2001, 57, 6311
21
22. Mechanism of Wacker-Tsuji oxidation reaction
Steps involved-
1. Pd and alkene complex formation
2. Hydroxy palladation
3. Hydride transfer
4. Beta elimination and formation of product
22
23. 9. Criegee Oxidation
General Reaction scheme
- Reaction in which vicinal diols converted into aldehydes and ketones
- Oxidizing agent – lead tetraacetate
1. Glycol cleavage in natural product synthesis
2. Synthesis of aldehydes and ketones from vicinal diols
Applications of Criegee oxidation
23
25. 10. Hass Bender Oxidation
General Reaction scheme
- Reaction in which benzyl halides converted into benzaldehydes
- Oxidizing agent – sodium salt of 2-nitropropane
Applications of Hass-Bender oxidation
1. Synthesis of aromatic aldehydes which are useful as flavors, fragrances
and pharmaceutical precursors
25
26. Mechanism of Hass Bender oxidation reaction
Steps involved
1. Deprotonation of 2-nitropropane
2. Formation of in-situ oxidant
3. Attack of oxidant on benzyl carbon
4. Formation of dimethyl oxime and forms
product
26
27. 11. Lindgren- pinnick Oxidation
General Reaction scheme
- Reaction in which aldehydes are selectively converted into acids
- Oxidizing agent – sodium chlorite
27
28. Mechanism of Lindgren- pinnick oxidation reaction
Steps involved
1. Formation of active oxidant
2. Then chlorous acid adds to the carbonyl carbon
3. Aldehydic Hydrogen transfer to the oxygen on
chlorine
28
