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Question

In the given sequence reaction which of the following is the correct structure of compounds A?


A
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B
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C
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D
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Solution

The correct option is C
Ozonolysis of alkenes involves the addition of ozone molecule to an alkene to form ozonide. Cleavage of ozonide by ZnH2O to smaller oxidised molecules.
H2/Ni gives catalytic hydrogenation of alkenes.
Calalytic hydrogenated product gives a cyclohexane ring so the compound (A) should have a six membered cyclic ring.
Also in ozonolysis product we have 2 moles of formaldehyde which indicated two terminal alkenes in the compound (A).
Option (b) does not have two terminal alkene so it is a wrong one.
Also option (d) has totally 11 carbon atom so it does not fits the given molecular formula of A so it can be eliminated.
Comparing (a) and (c)
When we done ozonolysis on compound (a), it gives 3 keto group and 1 aldehyde group.
When we done ozonolysis on compound (b), it gives 2 keto and 2 aldehyde group.
Thus, compound (c) is the correct reactant.

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