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Draw the alkene that would yield the following products via ozonolysis

Chemistry Jan 21, 2021

Draw the alkene that would yield the following products via ozonolysis.

Expert Solution

Ozonolysis of the alkene, cleave the double bond into two carbonyl group; these carbonyl carbons were part of the double bond.

The given carbonyl compounds were obtained from their respective alkene precursor as given below:Explanation | Common mistakes | Hint for next step

Structure of pair of carbonyl compounds is depicted in Step-1; it was known that they were obtained by ozonolysis of alkenes. Since double bonds were broken into two carbonyl groups, the carbon atoms involved in the double bond will be converted into carbonyl carbon. The aldehyde will result from the double bond with one hydrogen atom; if the carbon is bonded with two carbon atoms and a double bond, then it will result in a keto group. Aromatic double bonds cannot cleave using ozonolysis reaction.

2.Explanation | Common mistakes

Alkene on ozonolysis are converted into their two carbonyl groups; the carbonyl carbon originates from the carbon atom involved in the double bond; if the alkene contains hydrogen atom along the double bond, then the resultant carbonyl compound will be an aldehyde derivative. Ozonolysis of the double bond of cyclic compound will not cleave alkene into two different fragments, but there will be a ring opening, while in case of acyclic double bond, the alkene will be fragmented into carbonyl fragments. Thus, the alkene precursor of the given carbonyl compounds is identified and given in Step-2.

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