Question

2. Ozonolysis of alkenes can give the carbonyl products illustrated below. Supply an alkene that can produce the carbonyl compounds shown. Specify the nature of the workup step in the process (oxidation or reduction). o o a) HO [From two starting materials, 1. CH10. 2. C12H201

Answer 1

Ozonolysis of alkene -- Oxidative cleavage of alkene using ozone (03) to give two carbonyl compounds is called ozonolysis. In ozonolysis carbon-carbon single bond of alkene and carbon-carbon double bond of alkene are broaken. Ozone react with alkene by 113 dipolar cycloaddition Reaction followed by rearrangement reaction to give ozonide. Ozonide can be cleaved oxidatively using H202 to give carboxylic acid and ketone. Ozonide can be cleaved reductively to give aldehyde and ketone using Meas or an · Nature of product depends on structure of alkene and Method is used for reaction. CH₃ . CH3 ctc. CH3 003 Cho Heche - CH2 - CH₂ ® Meas F Croto ICHA-CH3 CH₂ CH₂ HC-HC 03 Meas Reduction ozonide Here ozonide undergo reductive cleavage to give Ketone in presence of Mezs.

L IITICIL Signature CH3 H 103 H₂CHE CHE-CH, O CHE CHES HE THE Otoc NO сн,-ен, re H ② O₃ Mezs Ctrl ΟΥ - zn Reduction ozonide In this reaction ozonide undergo reductive cleavage to give aldehyde and ketone.

©o OH Decoraz ukry 03 o H202 I cool -O oxidation L cool ozonide Here ozonide undergo oxidative eleavage to give carboxylic acid. ż 100 2 Hó H202 oxidation