Propanal and pentan-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?
Solution and Explanation
Given:
Ozonolysis products are:
- Propanal: CH3–CH2–CHO
- Pentan-3-one: CH3–CH2–CO–CH2–CH3
Concept used:
Ozonolysis cleaves the C=C double bond of an alkene and converts each double-bonded carbon into a carbonyl group.
- If a carbonyl product is an aldehyde, the original alkene carbon had at least one hydrogen.
- If the product is a ketone, the alkene carbon had two alkyl groups.
Reconstruction of the alkene:
Propanal indicates one side of the double bond was:
CH3–CH2–CH=
Pentan-3-one indicates the other side of the double bond was:
=C(CH2CH3)2
Structural formula of the alkene:
CH3–CH2–CH = C(CH2CH3)2
Conclusion:
The alkene which on ozonolysis gives propanal and pentan-3-one is:
CH3–CH2–CH = C(CH2CH3)2
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