The document summarizes two organic reactions: the Dieckmann reaction and ozonolysis reaction. The Dieckmann reaction involves the intramolecular condensation of diesters in the presence of a strong base to form β-keto esters via a 5-exo-trig cyclization. It is used to synthesize cyclopentane and cyclohexane derivatives. Ozonolysis involves the cleavage of unsaturated bonds like alkenes and alkynes with ozone to form carbonyl groups. It can be used to oxidize alkenes into alcohols, aldehydes, ketones or carboxylic acids and is useful for structure elucidation of unknown compounds containing carbon-carbon double bonds.

1. ADVANCED ORGANIC CHEMISTRY
Presented by : Niket D.Bajare [M.pharm First year]
Guided by :Dr S. Pekamwar
School of Pharmcy ,Nanded.

2. Mechanism and Synthetic Application of Naming
reaction
• DIECKMANN REACTION
• OZONOLYSIS REACTION

3. DIECKMANN REACTION
-It is named after the german chemist Walter
Dieckmann (1869-1925)
-certain diesters undergoes intramolecular condensation
in the presence of strong base to produce B-keto esters
this called as “Dieckmann condensation reaction”.
-its ring forming reaction.

4. General Reaction :-

5. Mechanism.......
-Deprotonation of an ester at the alpha-position
generates an enolate ion which then undergoes a 5-
exo-trig nucleophilic attack to give a cyclic enol.
-protonation with a Bronsted-Lowry acid reforms
the Beta-keto ester.

6. Mechanism.........

7. synthetic application..........
• It is used in the synthesis of various
cyclopentane &cyclohexane derivative.
• it is used in preparation of cyclic
indole.(active against cancer)

8. OZONOLYSIS

9. what is ozonolysis ?
• OZONOLYSIS is an organic reaction where the unsaturated
bonds of alkenes,alkynes or azo compound are cleaved with
ozone .
• alkenes and alkynes form organic compound in which the
multiple carbon-carbon bond has been replaced by a carbonyl
group.while azo compound form nitrosamines.
• the out come of reaction depends on the type of multiple bond
being oxidised and work up condition.

10. ozonolysis of alkenes.............
• alkenes can oxidised with ozone to form
alcohol,aldehyde,or ketone or carboxylic acid.
• e.g- tetramethyl alkene which is undergoes
ozonolysis in methanol at -78dc. to form the prop-
2-one and small amount of acids.

11. reaction

12. Mechanism ....
• The alkene and ozone form an intermediate molozonide
in a 1,3-dipolar cycloaddition.
• the molozonide reverts to its corresponding carbonyl
oxide and aldehyde or ketone in a retro-1,3-dipolar
cycloaddition.
• the oxide and aldehyde or ketone react again in a 1,3-
dipolar cycloaddition or produce a relatively stable
ozonide intermediate (a trioxolane )

14. Synthetic application....
• It is used for structure elucidation of unknown organic
compound containing carbon carbon double bond(c=c).
CH3 (CH2)7 CH CH (CH2)7 COOH CH3 (CH2)7 COOH
pelargonic acid
O31)
2) H2O2
Oleic acid
HOOC (CH2)7 COOH
Azelaric acid
+

15. References :-
• Organic chemistry Clayden, Greeves,Warren & Woihers .,
Oxford University.
• Wikipedia