Q.What is Ozonolysis? How it can be used to determine the position of double bond in an unknown alkene? OR Write short notes on the following:
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Start your 14-day free trial to unlock the full solution →Ozonolysis breaks a C=C double bond exactly at its location, producing two carbonyl compounds whose identities reveal where the double bond was.
Ozonolysis is a reaction in which an alkene is treated with ozone (O3), which adds across the C=C double bond to form a cyclic intermediate called an ozonide. This ozonide is unstable and is not isolated directly; instead it is decomposed (reductive workup) using zinc dust and water (Zn/H2O) — zinc is used specifically to prevent the further oxidation of any aldehyde products to carboxylic acids by the H2O2 that would otherwise form.
General reaction: R2C=CR'2 --(i) O3,
(ii) Zn/H2O--> R2C=O + R'2C=O
The double bond is cleaved exactly at the position it occupied, and each of the two original alkene carbons becomes the carbon of a new carbonyl (C=O) group; if the alkene carbon had two alkyl/hydrogen substituents, an aldehyde forms, and if it had two alkyl substituents (no H), a ketone forms.
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