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An organic compound contains 69.77% carb...

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.

Text Solution

Verified by Experts

Step-1 : 1 to determine the molecular formula of the compound.

Emperical formula of the given compound `=C_(5)H_(10)O`
Molecular formula `=n xx ` (emperical formula)
Where n`=("Molecular mass of the compound")/("Emperical formula mass of compound")`
Given , molecular mass =86
Emperical formula mass of `C_(5)H_(10)O =(12xx5)+(10xx1)+16=60+16=86`
`n=(86)/(86)=1`
Molecular formula `=1xx(C_(5)H_(10)O)`
`therefore ` Molecular formula `=C_(5)H_(10)O`
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Knowledge Check

  • An alcohol (A) on dehydration gives (B) which on ozonolysis gives two products C & D (D) gives positive iodoform test and on heating with dilute alkali gives alpha . beta -unsaturated carbonyl compound (E) which does not gives positive iodoform test. (C) on oxidation gives a mono basic acid (F) Ag salt of (F) contains 59.6% Ag. Oxime of (D) contains 16.09% nitrogen. the structure of (A) is

    A
    `CH_3(CH_2)_2 C(CH_3)(OH)CH_2 CH_3`
    B
    `CH_3CH_2 CH(OH) CH (CH_3)C_2 H_5`
    C
    `CH_3 CH_2 C (CH_3)(OH) CH_2 CH_3`
    D
    `CH_3CH_2 CH (OH) (CH _3)_2`

  • An alcohol (A) on dehydration gives (B) which on ozonolysis gives two products C & D (D) gives positive iodoform test and on heating with dilute alkali gives alpha . beta -unsaturated carbonyl compound (E) which does not gives positive iodoform test. (C) on oxidation gives a mono basic acid (F) Ag salt of (F) contains 59.6% Ag. Oxime of (D) contains 16.09% nitrogen. structure of D is

    A
    `CH_3 CH_2 COCH_3`
    B
    `(CH_3)_2 CO`
    C
    `CH_3 CH_2 CHO`
    D
    `(C_2H_5 )_2 CO`

  • An alcohol (A) on dehydration gives (B) which on ozonolysis gives two products C & D (D) gives positive iodoform test and on heating with dilute alkali gives alpha . beta -unsaturated carbonyl compound (E) which does not gives positive iodoform test. (C) on oxidation gives a mono basic acid (F) Ag salt of (F) contains 59.6% Ag. Oxime of (D) contains 16.09% nitrogen. the structure of (E ) is given reaction is

    A
    `(CH_3)_2CC HCOCH_2 CH_3`
    B
    `CH_3 CH_2 C(CH_3)CHCOCH_2 CH_3`
    C
    `CH_3 CH_2 CH=CHCOCH_2 CH_3`
    D
    `CH_3 CH_2 =C (CH_3)CHO`

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