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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 resolved into enatiomers. A does not decolourise bromine water solution. A on reflxing with dilute `H_(2)SO_(4)` yields another resolable compound `B(C_(9)H_(14)O_(3))` which gives effervescence with `NaHCO_(3)`. B on treatemet with `NaBH_(4)` yields `C(C_(9)H_(16)O_(3))` on heating with concentrated `H_(2)O_(4)` yields ester `D(C_(9)H_(14)O_(2))`. Compound A on reduction with `LiAIH_(4)`, followed by treatement of `H_(2)SO_(4)` yields following compound:

Due to reduction of optically pure 'B' two isomeric product 'C' form. Isomeric product 'C' are:

A

Enantiomers

B

Diastereomers

C

Position isomers

D

Functional isomers

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 resolved into enatiomers. A does not decolourise bromine water solution. A on reflxing with dilute H_(2)SO_(4) yields another resolable compound B(C_(9)H_(14)O_(3)) which gives effervescence with NaHCO_(3) . B on treatemet with NaBH_(4) yields C(C_(9)H_(16)O_(3)) on heating with concentrated H_(2)O_(4) yields ester D(C_(9)H_(14)O_(2)) . Compound A on reduction with LiAIH_(4) , followed by treatement of H_(2)SO_(4) yields following compound: Find out structure of compound 'A' :

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