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 aditional compound with sodium hydrogensulphite and gives positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acid. Write the possible structure of the compound.

Explanation

Step 1 to determine the molecular formula of the compound
` % C = 69.77, % H = 11.63 `
` % O= 100-(69.77+11.63 ) = 18.60 `
simple atomic ratio
`C : H : O = ( 69.77 )/( 12 ) :(11.63 )/( 1 ) : ( 18.6 ) /( 16 ) `
`= 5.88 : 11.63 : 1.16 `
` = 5 : 10 :1`
Empirical formula `=C_8 H_(10) O`
Empriical formula mass `= 5 xx 12 +10 xx 1 +1 xx 16 =86`
Molecular formula mass = 86
` n=("Molecular formula mass ")/( E.F mass ")`
`=( 86 )/( 86 ) = 1`
` therefore ` Molecular formula ` =C_8 H_(10) O`
step 2 : Determining the structure of the compound
( i) since the given compound forms sodium hydrogen sulphite addition product , ti must be an aldehyde or a ketone (ii ) since the compound does not reduce Tollen.s reagent, therefore , it cannot be an aldehyde and it must be a ketone
(iii ) Since the compound gives iodoform test , therefore , the compound must be methyl ketone .
(iv ) Since the compound on vigorus oxidation gives a mixture of ethanoic acid and propanoic acid , therefore , the methyl ketone is pentan -2 - one i.e,