Subjective Type

An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of the compound is 86. It does not reduce Tollens reagent but forms an addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acid. Write the possible structure of the compound.

Solution

An organic compound contains $$69.77\%$$ carbon, $$11.63\%$$ hydrogen and rest oxygen. The molecular mass of the compound is $$86$$.
$$\%O =$$ $$\displaystyle 100-(69.77 + 11.63) = 18.60$$
Simple atomic ratio $$\displaystyle C:H:O = \dfrac {69.77}{12} : \dfrac {11.63}{1} : \dfrac {18.6}{16} = 5.88 : 11.63 : 1.16 = 5 : 10: 1$$
The empirical formula is $$\displaystyle C_5H_{10}O$$
Empirical formula mass $$\displaystyle = 5 \times 12 + 10 \times 1 + 1 \times 16 = 86$$. It is equal to molecular formula mass. Hence, molecular formula is same as empirical formula.
It does not reduce Tollens reagent. Hence, it is not an aldehyde
It forms an addition compound with sodium hydrogensulphite.
Hence, it contains carbonyl group.
It give positive iodoform test.
Hence, it is a methyl ketone
On vigorous oxidation it gives ethanoic and propanoic acid.
Hence, it is $$2$$-pentanone.
$$\displaystyle CH_3COCH_2CH_2CH_3 \xrightarrow [ Vigorous] {O} CH_3CH_2COOH + CH_3COOH$$

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