Choose the correct answer among the alternatives given:
A compound 'A' having the molecular formula $C_{5} H_{12} O$ , on oxidation gives a compound 'B' with molecular formula $C_{5} H_{10} O$ . Compound 'B' gave a 2,4-dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound 'A' is :

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

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

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

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

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Solution

The correct option is C $C H_{3} - C H_{2} - C | O H H - C H_{2} - C H_{3}$
Since, only aldehyde gives positive silver mirror test =, and for ketone it is not feasable and to have a ketone upon oxidation of alcohol, alcohol should be secondary not primary since primary alcohol gives aldehyde on oxidation. So structure would be $C H_{3} - C H_{2} - C | O H H - C H_{2} - C H_{3}$

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

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

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

H C O O H

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

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