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Question

The alkene which gives 4,4-dimethylpentan-2-one on reductive ozonolysis is

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 A

Ozonolysis of alkenes involves the addition of an ozone molecule to an alkene, to form an ozonide. Formed ozonide undergoes cleavage by Zn/H2O to give smaller oxidised product.
Compound (a) undergo ozonolysis to give formaldehyde and 4, 4-dimethyl pentan-2-one.


Mechanism of Ozonolysis:
Step 1: The double bond in the compound (a) attacks the ozone molecule O3 to form a five membered ring like structure. Then the rearrangement take place to form a cyclic peroxide derivative called ozonide.

Step 2: Formed ozonide in presence of Zn/H2O gets reductively cleaved to form formaldehyde and 4, 4-dimethyl pentan-2-one.


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