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An organic compound (A) (molecular formu...

An organic compound (A) (molecular formula `C_(8)H_(16)O_(2))` was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C ). Oxidation of (C ) with chromic acid produced (B). (C ) on dehydration gives but-1-ene. Write equations for the reactions involved.

Text Solution

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i. Hydrolysis of (A) to acid alcohol suggests that (A) is an ester.
ii. Formation of (D) suggests that (C ) is 4C-atom `1^(@)` alcohol.
iii. Oxidation of (C ) to (B) suggests that (C ) is a `1^(@)` alcohol.
iv. Total C atom in (A) are eight, so acid (B) is a 4C-atom acid.
v. D.U. in `A= ((2n_(C)+2)-n_(H))/(2)=((2xx8+2)-16)/(2)=1^(@)`
1 D.U. in (A) suggests (A) is an ester
`(R-overset(O)overset(||)C-OR`, having 1 D.U.).
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Knowledge Check

  • A compound (X) having molecualr formula C_(4)H_(8)O_(2) is hydrolysed by water in presence of an acid to give a carboxylic acid (Y) and an alcohol (Z). (Z) on oxidation with chromic acid gives (Y), (X), (Y) and (Z) are

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