An organic compound of molecular formula $C_{3} H_{6} O$ did not give a silver mirror with Tollen's reagent, but gave an oxime with hydroxylamine, it may be:

C H_{3} C O C H_{3}

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C_{2} H_{5} C H O

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C H_{2} = C H - C H_{2} - O H

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C H_{3} - O - C H = C H_{2}

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Solution

The correct option is A $C H_{3} C O C H_{3}$
(i) Organic compound give an oxime with hydroxyl amine, therefore, it must be an aldehyde or ketone.
(ii) Organic compound did not give silver mirror with Tollen's reagent, therefore it cannot be an aldehyde. Therefore, compound is ketone and its molecular formula with be $C H_{3} C O C H_{3}$ .

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C H_{3} - C H_{2} - O H | C H - C H_{2} - C H_{2} - C H_{2} - C H_{2} - C H_{2} - C H_{2} - C H_{2} - C H_{2} - C H_{3} | C H - C H_{3}

C H_{3} - C H = C H - C H_{2} - O | | C - C H_{3} \to C H_{3} - C H = C H - C H_{2} - O | | C - O H

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