Question 8.3: What alkene would yield a mixture of cyclopentanone and prop...

Predicting the Reactant in an Ozonolysis Reaction

What alkene would yield a mixture of cyclopentanone and propanal on treatment with ozone followed by reduction with zinc?

S t r a t e g y
Reaction of an alkene with ozone, followed by reduction with zinc, cleaves the C=C bond and gives two carbonyl-containing fragments. That is, the C=C bond becomes two C=O bonds. Working backward from the carbonyl-containing products, the alkene precursor can be found by removing the oxygen from each product and joining the two carbon atoms to form a double bond.