Which of the compound with molecular formula C5H10 yields acetone on ozonolysis?
- 3-Methyl-1-butene
- Cyclopentane
- 2-Methyl-1-butene
- 2-Methyl-2-butene
Answer
(4) 2-Methyl-2-butene
Solution
On ozonolysis each doubly bonded carbon becomes a C=O group. To get acetone, one carbon of the C=C bond must carry two CH3 groups.
2-Methyl-2-butene: CH3- CH3 |C=CH-CH3
⇒ CH3- CH3 |C=CH-CH3 [Zn/H2O]O3
CH3- O \|C-CH3 + CH3CHO
3-Methyl-1-butene gives (CH3)2CHCHO + HCHO; 2-methyl-1-butene gives butan-2-one + HCHO; cyclopentane has no C=C bond.
∴ 2-Methyl-2-butene yields acetone.
Answer: (4)