Study of Mechanism & Application of Name Reaction: Ozonolysis Michael Addition Reaction

Study of Mechanism &
Application of Name Reaction

Ozonolysis
Michael addition reaction
Submitted to Presented by
Dr.S.R. Butle M. Pharm, Ph. D Sanket Kore
( M Pharm First year )
OZONOLYSIS
• Ozonolysis is a widely used reaction in organic synthesis. The reaction was

invented by Christian Friedrich Schoenbein in 1840.
• Alkenes and alkynes are the most common substrates for the Ozonolysis
reaction.
• Ozonolysis was an important diagnostic tool for the determination of the

position of unsaturation in unknown molecules before the invention and
development of spectroscopic techniques for identification and
characterization of organic molecules.
• The reaction was used for structure elucidation work because it provided
chemists with smaller and more readily identifiable carbonyl compounds.
Ozonolysis of alkenes
• The ozonolysis reaction involves bubbling ozone into a solution of olefin in an organic solvent.
• The reaction is rapid and produces an intermediate called ozonide.
• The ozonide is unstable, and hence not isolated, but can be further reacted with various reagents to
give aldehydes, ketones, carboxylic acids, alcohols etc.
• When the ozonide is treated with mild reducing agents like phosphines and thio compounds
(typically dimethyl sulfide or thiourea is used) aldehydes and ketones are produced.
• Ozonides can be treated with strong reducing agents like sodium borohydride to produce alcohols.
• Ozonides when treated with oxidizing agents such as oxygen or hydrogen peroxide, they produce
carboxylic acids as the products.
An example is the ozonolysis of eugenol converting the terminal alkene to an aldehyde
Ozonolysis of alkynes
• Alkynes also undergo ozonolysis but very slowly

compared to alkenes.
• Unlike alkenes, ozonides from alkynes do not
need either an oxidizing agent or reducing agent
to provide end products.
• Ozonides from alkynes upon treatment with water
provide carboxylic acids are products.
• Internal alkynes produce two different carboxylic
acids while terminal alkynes produce carboxylic
acid with one less carbon; the terminal carbon is
converted to carbon dioxide.
Ozonolysis of alkynes
Ozonolysis of alkanes
•
• Alkanes get oxidized when treated with ozone. The products

formed are alcohols, aldehydes/ketones or carboxylic acids. The
rate of oxidative cleavage of alkanes is highest for tertiary C-H bond,
followed secondary and primary.
Ozonolysis of elastomers
• Ozone cracking is a form of stress corrosion
cracking where active chemical species attack
products of a susceptible material. Ozone
cracking was once commonly seen in the
sidewalls of tires but is now
• rare owing to the use of antiozonants. Other
means of prevention include replacing
• Susceptible rubbers with resistant elastomers
such as polychloroprene, EPDM or viton.
Ozonolysis in industry
• Ozonolysis has been used frequently in major drug syntheses such
as (+)-artemisinin, indolizidine 251F and D,L- camptothecin , as well
as in fine chemical syntheses such as L-isoxazolylalanine and
prostaglandin endoperoxides.
• Thales Nano has developed the Ice Cube reactor to overcome these
disadvantages. When combined with the ozone module, ozonolysis
can be performed in a safe and highly controlled manner.
Ozonolysis has a number of advantages over

conventional oxidation methods, including:
•Quicker reactions with improved yields

•Cleaner reactions and less side products
•Does not require addition of water
Michael Addition Reaction
Synthetic Reagent & Applications
Aluminium isopropoxide
N-bromosuccinamide
ALUMINIUM ISOPROPOXIDE 1
• It is used as a catalyst and an intermediate in different reactions.
• This belongs to aluminum alkoxide group.
• Widely used as a reducing agent for aldehydes and ketones.
• It is an inexpensive and easy to handle among the other alkoxides.
SYNONYMS:
• Tri isopropoxy aluminum
• Aluminum isopropoxylate
• 2-proponol aluminum salt.
STRUCTURE:
PHYSICAL PROPERTIES:-
• It is a white solid and the molecular formula of aluminum isopropoxide is Al(O-i-Pr)3.
• It is more soluble in benzene and less soluble in alcohol.
• The boiling point of aluminum isopropoxide is 1400 C.
• The melting point is 128-1330 C.
• It is highly flammable and irritant.
• It is moisture sensitive so it must be stored in air tight container.
• Carbonyl compounds are reduced to the respective alcohol in the presence of
aluminum isopropoxide.
• The acetone, so formed is removed by slow distillation and hence the reaction proceeds
only in the desired direction.
It is used in oppenauer oxidation (alcohol to ketone in the presence

of aluminum isopropoxide).
2.N-BROMO SUCCINIMIDE2-3
PHYSICAL PROPERTIES:-
•It is a white solid.
•Molecular formula of NBS is C4H4BrNo2.
•It is soluble in CCl4 and insoluble in water.
•The boiling point of NBS is 3390 C and the melting point is 175-1780 C.
Application of N-bromosuccinamide (NBS)

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Study of Mechanism &

Application of Name Reaction

• Ozonolysis is a widely used reaction in organic synthesis. The reaction was

• Ozonolysis was an important diagnostic tool for the determination of the

• The reaction is rapid and produces an intermediate called ozonide.

• Alkynes also undergo ozonolysis but very slowly

• Alkanes get oxidized when treated with ozone. The products

Ozonolysis has a number of advantages over

•Quicker reactions with improved yields

It is used in oppenauer oxidation (alcohol to ketone in the presence

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