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An organic compound ‘A’ has molecular fo...

An organic compound ‘A’ has molecular formula `C_(9)H_(13)NO` and it can be resolve into enantiomers. Adoes not decolourise bromine water solution. A on refluxing with dilute `H_(2)SO_(4)`, yields another revolvable compound `B(C_(9)H_(14)O_(3))` which give effervescence with `NaHCO_(3)`. B on treatment with `NaBH_(4)` yields `C(C_(9)H_(16)O_(3))` on heating with concentrated `H_(2)SO_(4)` yields ester D `(C_(6)H_(14)O_(2))`.
Compound A on reduction with `LiAlH_(4)` followed by treatment of `H_(2)SO_(4)` yields following compound :

Find out structure of compound 'A''

A

B

C

D

Text Solution

Verified by Experts

The correct Answer is:
B
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An organic compound ‘A’ has molecular formula C_(9)H_(13)NO and it can be resolve into enantiomers. Adoes not decolourise bromine water solution. A on refluxing with dilute H_(2)SO_(4) , yields another revolvable compound B(C_(9)H_(14)O_(3)) which give effervescence with NaHCO_(3) . B on treatment with NaBH_(4) yields C(C_(9)H_(16)O_(3)) on heating with concentrated H_(2)SO_(4) yields ester D (C_(6)H_(14)O_(2)) . Compound A on reduction with LiAlH_(4) followed by treatment of H_(2)SO_(4) yields following compound : The sweet smelling neutral compound D is

An organic compound ‘A’ has molecular formula C_(9)H_(13)NO and it can be resolve into enantiomers. Adoes not decolourise bromine water solution. A on refluxing with dilute H_(2)SO_(4) , yields another revolvable compound B(C_(9)H_(14)O_(3)) which give effervescence with NaHCO_(3) . B on treatment with NaBH_(4) yields C(C_(9)H_(16)O_(3)) on heating with concentrated H_(2)SO_(4) yields ester D (C_(6)H_(14)O_(2)) . Compound A on reduction with LiAlH_(4) followed by treatment of H_(2)SO_(4) yields following compound : Due to reduction of optically pure 'B'two isomeric product 'C' form. Isomeric product 'C' are :

Knowledge Check

  • C_(4)H_(4)O_(4) can be

    A
    A cyclic ester of dibasic acid
    B
    A cis-dibasic acid
    C
    A trans-dibasic acid
    D
    All true

  • Compounds with C_(4)H_(11)N as molecular formula can exhibit

    A
    Position isomerism
    B
    Metamerism
    C
    Functional isomerism
    D
    All the three

  • An organic compound with molecular formula C_(3)H_(5)N on hydrolysis gives an acid. The acid on heating with N_(3)H and conc. H_(2)SO_(4) gives

    A
    Propanamide
    B
    Ethyl acetate
    C
    Methyl amine
    D
    Ethyl amine

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