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Q 12.11    An organic compound (A) (molecular formula C _8H_{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.

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  • Organic compound (A) hydrolysed with H_{2}SO_{4} gives carboxylic acid (B) and alcohol (C). So, it means compound A must be a ESTER.
  • Oxidation of C with chrmoic acid produces B, so it means compound C and B must have same number of carbon atom. We know that A have total 8 carbon atom, so B and C have 4 carbon atom.
  • C on hydration give but-1-ene ,so it means compound C is butanol (straight chain).
  • On oxidation of compound C it give butanoic acid. So, B is a also butanoic acid
     

So, finally the structure of the ester of molecular formula C _8H_{16}O_{2} is -

By following reaction we can understand it in a better way-

 

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manish

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