Name Reactions DR.S.D.PATIL Associate Professor in Chemistry Shivraj College Gadhinglaj.

E mail: [email protected] Mobile:9421112225, Blog- sdpatilnsr.blogspot.in

Joseph Lister, 1st Baron Lister, Bt., OM, FRS, PC (5 April 1827 – 10 February 1912)

Thomas Jefferson 1743-1826

Chemistry stirs extreme emotions…. If you are obliged to neglect anything, let it be chemistry. It is the least useful and the least amusing…of all the ordinary branches of science. -Thomas Jefferson

Chemistry like all other sciences had arisen from the reflections of ingenious men on the general facts which occur in the practice of the various arts of common life." - Joseph Black (1728-99)

 Joseph Black (16 April 1728 – 6 December 1799) was a Scottish physician and chemist.  Discovered of magnesium, latent heat, specific heat, and carbon dioxide.  Professor of Anatomy and Chemistry at the University of Glasgow for 10 years from 1756, and then  Professor of Medicine and Chemistry at the University of Edinburgh from 1766, teaching and lecturing there for more than 30 years.

Wöhler, Friedrich (1800-82)

German. Worked with Jöns Jakob Berzelius Swedish.

A letter to Berzelius from Friedrich Wohler, Berlin, Feb. 22nd,1828 "I must now tell you, that I can make urea without calling on my kidneys, and indeed without the aid of any animal, be it man or dog."

Friedrich Wohler writes to J J Berzelius in 1835 …….

"Organic chemistry appears to me like a primeval forest of the tropics, full of the most remarkable things".

Accidental synthesis of urea KCNO + NH4Cl

NH4CNO

(NH2)2CO

Linus Pauling 1901-1994 NL 1954 and 1982

Chemistry stirs extreme emotions…. I feel sorry for people who don’t know anything about chemistry. They are missing an important source of happiness - Linus Pauling

The achievements of chemical synthesis are firmly bound in our attempts to break the shackles of disease and poverty” Roald Hofmann, NL1981

(1981 Nobel Prize in Chemistry)

Because it is so challenging to do, ….synthesis is often compared metaphorically with climbing mountains. However, I prefer to think of syntheses using a musical metaphor, because I see in them a clear and lasting beauty. Elias J. Corey, NL 1990

‘Study the past, if you would define the future’ Antoine Lavoisier 1743-1794

Unit I. Name reactions. [08] Statement, General Reaction, Mechanism and Synthetic applications 1. Diels -Alder reaction 2. Oppenauer Oxidation 3. Meerwein – Pondorff-Verley reduction 4. Schmidt rearrangement 5. Hofmann rearrangement 6. Wittig reaction 7. Wagner- Meerwein rearrangement 8. Favorskii rearrangement 9. Michael reaction 10.Dieckmann’s reaction or condensation

Henry Rzepa Chemistry with a twist Professor of Computational Chemistry, Imperial College London

Henry Rzepa Unravelling reaction mechanisms is thought to be a 20th century phenomenon. Coincident with the development of electronic theories of chemistry. Hence electronic arrow pushing as a term. But here I argue that the true origin of this immensely powerful technique in chemistry goes back to the 19th century.

Henry Armstrong British Chemist (6 May 1848 – 13 July 1937) In 1890, Henry Armstrong proposed what is close to the modern mechanism for the process we now know as aromatic electrophilic substitution . He invented what is now known as the Wheland Intermediate (about 50 years before Wheland wrote about it, and hence I argue here it should really be called the Armstrong / Wheland intermediate).- Henry Rzepa

1. Diels -Alder reaction The Diels–Alder reaction is a [4+2] cycloaddition between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system.

1. Diels -Alder reaction

Dienes

Dienophiles

NL 1950

It was first described by Otto Paul Herman Diels and Kurt Alder in 1928, for which work they were awarded the Nobel Prize in Chemistry in 1950.

The Diels–Alder reaction is particularly useful in synthetic organic chemistry as a reliable method for forming 6-membered systems with good control over regio- and stereochemical properties.

Name of Reaction Substrate Reagent / Catalyst Intermediate/ Product

Diels -Alder reaction Diene and dienophile Inert Solvent Adduct Cyclo-addition product

Mechanism Applications

Concerted ( or consecutive?)

2. Oppenauer oxidation Oppenauer oxidation, named after Rupert Viktor Oppenauer, is a gentle method for selectively oxidizing secondary alcohols to ketones. The reaction is the opposite of M.P.V. Reduction. The alcohol is oxidized with aluminium isopropoxide in excess acetone.

2. Oppenauer oxidation

Oppenauer oxidation

The oxidation is highly selective for secondary alcohols and does not oxidize other sensitive functional groups such as amines and sulfides.[2] 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 Oppenanuer oxidation is commonly used in various industrial processes such as the synthesis of steroids, hormones, alkaloids, terpenes, etc.

Name of Reaction Oppenauer Oxidation Substrate Secondary Alcohol and Ketone Reagent / Catalyst Aluminium tert butoxide Intermediate/ Cyclic intermediate Product Ketone and alcohol Mechanism Applications

Hydride Transfer Synthesis of Steroids, hormones, alkaloids, terpenes

3. Meerwein – Pondorff – Verley reduction

Hans Meerwein (1879-1965)

Carl Ernst Heinrich Schmidt (1822 –1894)

The MPV reduction was discovered by Meerwein and Schmidt, and separately by Verley in 1925. They found that a mixture of aluminium ethoxide and ethanol could reduce aldehydes to their alcohols.

Ponndorf applied the reaction to ketones and upgraded the catalyst to aluminium isopropoxide in isopropanol.

Name of Reaction Substrate Reagent / Catalyst Intermediate/ Product

M.P.V. Reduction Aldehyde or Ketone Aluminium isopropoxide Cyclic intermediate Alcohol

Mechanism Applications

Hydride Transfer Synthesis of alcohols

4. Schmidt rearrangement The acid-catalysed reaction of hydrogen azide with electrophiles, such as carbonyl compounds, tertiary alcohols or alkenes. After a rearrangement and extrusion of N2, amines, nitriles, amides or imines are produced

Schmidt rearrangement

Carbonyl to amide

Name of Reaction Schmidt rearrangement Substrate Acid, aldehyde, ketone, alcohol, unsaturated compounds Reagent Hydrogen azide Catalyst Protic or Lewis acid Intermediate/ With HN3 Product Depends on reactant Mechanism Applications

Rearrangement from C to N Several synthesis

5. Hofmann rearrangement

• The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one fewer carbon atoms.

August Wilhelm von Hofmann (8 April 1818 – 5 May 1892) German

August Wilhelm von Hofmann (8 April 1818 – 5 May 1892) German

He was student of law and philology. When his father enlarged Liebig’s Giessen laboratories in 1839. August Wilhelm changed his studies to chemistry, and studied under Justus von Liebig. He obtained his Ph.D. there in 1841. In 1843, after his father's death, he became one of Liebig's assistants

Name of Reaction Substrate Reagent Intermediate/ Product

Hoffman rearrangement Amide Bromine and conc. alkali Isocyanate Amine

Mechanism

Rearrangement from

Hofmann at the Inauguration of the School of Chemistry in London.

Hofmann's methane model

Monument to Hofmann at Giessen

Hofmann voltameter

6. Wittig reaction The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide

Wittig reaction

Wittig reaction

NL 1979

Georg Wittig (June 16, 1897 – August 26, 1987) was a German chemist who reported a method for synthesis of alkenes from aldehydes and ketones using compounds called phosphonium ylides in the Wittig reaction. He shared the Nobel Prize in Chemistry with Herbert C. Brown in 1979

He became a lieutenant in the cavalry of Hesse-Kassel After being an English prisoner of war from 1918 till 1919, Wittig found it hard to restart his chemistry studies owing to overcrowding at the universities. By a direct plea to Karl von Auwers, who was professor for organic chemistry at the University of Marburg at the time, he was able to resume university study and after 3 years was awarded the Ph.D. in organic chemistry.

Name of Reaction Substrate Reagent Intermediate Product

Wittig Reaction Aldehyde or ketone Triphenyl phosphonium ylide Oxaphosphetane Alkene

Mechanism

Nucleophilic attack of ylide

The Wagner-Meerwein rearrangement is an organic reaction used to convert an

alcohol to an olefin using an acid catalyst.

7. Wagner- Meerwein rearrangement

Wagner- Meerwein rearrangement

Wagner- Meerwein rearrangement

The mechanism begins with protonation of the alcohol by the acid which is then released as water to forms a carbocation. A 1,2-shift then occurs to form a more substituted and stabilized carbo-cation. A final deprotonation with water produces the final olefin product and regenerates the acid catalyst.

Name of Reaction Wagner- Meerwein rearrangement Substrate Branched Alcohols, Halogen derivative Reagent Lewis, Bronsted acids Intermediate Carbocation Product Depends on condition Mechanism

Skeletal rearrangement

Favorskii rearrangement

• Favorskii rearrangement, named for the Russian chemist Alexei Yevgrafovich Favorskii. • Most principally a rearrangement of cyclopropanones and α-halo ketones which leads to carboxylic acid derivatives.

• In the case of cyclic α-halo ketones, the Favorski rearrangement constitutes a ring contraction. • This rearrangement takes place in the presence of a base, sometimes hydroxide, to yield a carboxylic acid but most of the time either an alkoxide base or an amine to yield an ester or an amide, respectively. α,α’-Dihaloketones eliminate HX under the reaction conditions to give α,βunsaturated carbonyl compounds.

Name of Reaction Substrate Reagent Intermediate Product

Favorski rearrangement α haloketones Alkoxide Anion Ester

Mechanism

Ring contraction

9. Michael reaction The Michael reaction or Michael addition is the nucleophilic addition of a carbanion or another nucleophile to an α,β-unsaturated carbonyl compound. It belongs to the larger class of conjugate additions. This is one of the most useful methods for the mild formation of C–C bonds

Michael reaction

Arthur Michael (August 7, 1853 – February 8, 1942) was an American organic chemist

Name of Reaction Substrate Reagent Intermediate Product

Michael Reaction Active methylene compound Basic Catalyst Anion Ester

Mechanism

Ring contraction

10.Dieckmann’s reaction or condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6membered cyclic ß-keto esters, and is usually effected with sodium alkoxide in alcoholic solvent.

Dieckmann’s reaction or condensation

Walter Dieckmann (8 October 1869 – 12 January 1925) was a German chemist.

Awards and Recognition

Dr. S. D. Patil has received Best Popular Science Book award of Government of Maharashtra for his Marathi Book Deshodeshiche Vidnyaneshwar - 2009.

304 B 207 Deshodeshiche Vidnyaneshwar Dr. Ajit Patil Maharashtra Govt Jan-11



Monday, 4 October, 2010 1:52 AM Dear Professor Ajit Patil , How are you doing ? We are doing fine on our side . We will be in Pune from Jan 7 to Mar 20 , 2011 .



I have almost finished reading your remarkable , stimulating and highly informative book and have recommended it to our Marathi Book Club here in West Windsor , NJ . Accordingly we started reading it in the Book Club last week and the members appreciate the book very much .



One of the members , Ashok Vidwans may contact you on tel or E-mail about a reference which you have given in the article on Bhakaracharya . In anticipation of your approval I have given him your cell tel no. and your Email address . Please convey my regards to Professor Kurade-Patil , Pricipal Jodgudri and Professor Khichadi .



With regards to you , Vijay V Joshi , MD , PhD , FRC Path .

Published Book on the great scientist Marie Curie to salute her in the International Year of Chemistry (IYC)- 2011

Great mind and great heart Should go together.

Five minds for the future

1.Disciplinary mind 2.Synthesizing mind 3.Creating mind 4.Respectful mind 5.Ethical mind

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