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

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Accepted Answer

1. **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.
2. **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=... $).
3. **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 $).
4. **Conclusion:** Only 2-methyl-2-butene yields acetone.

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