Solved: CHEMISTRY Question for NEET

NEET CHEMISTRYMedium

Which of the following compounds with molecular formula, C₅H₁₀ yields acetone on ozonolysis?

2-methyl-2-butene

3-methyl-1-butene

Cyclopentane

2-methyl-1-butene

Reaction Principle: Ozonolysis of an alkene involves the cleavage of the carbon-carbon double bond ( $C=C$ ) to form two carbonyl compounds ( $C=O$ ). The specific products depend on the structure of the alkene.
Target Product: The question asks for Acetone ( $CH_3COCH_3$ ) as a product. Acetone contains a carbonyl carbon bonded to two methyl groups. This implies the starting alkene must have a carbon atom doubly bonded to another carbon and singly bonded to two methyl groups ( $(CH_3)_2C=...$ ).
Analysis of Options:

Option A (2-methyl-2-butene): Structure is $CH_3-C(CH_3)=CH-CH_3$ . Ozonolysis cleaves the double bond. The left fragment ( $(CH_3)_2C=$ ) forms Acetone ( $CH_3COCH_3$ ). The right fragment ( $=CH-CH_3$ ) forms Acetaldehyde ( $CH_3CHO$ ).
Option B (3-methyl-1-butene): Structure is $CH_2=CH-CH(CH_3)_2$ . Cleavage yields Formaldehyde ( $HCHO$ ) and Isobutyraldehyde ( $(CH_3)_2CHCHO$ ).
Option C (Cyclopentane): This is a saturated cycloalkane and does not undergo ozonolysis under standard conditions.
Option D (2-methyl-1-butene): Structure is $CH_2=C(CH_3)CH_2CH_3$ . Cleavage yields Formaldehyde ( $HCHO$ ) and Butanone ( $CH_3CH_2COCH_3$ ).

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