An organic compound A with molecular formula C8H16O2 was hydrolyzed with dilute sulphuric acid to give a carboxylic acid (B) and alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives but-1-ene. Write equations for the reaction involved.
Step 1:
An organic compound A with molecular formula C8H16O2 gives a carboxylic acid (B) and alcohol (C) on hydrolysis with dilute sulphuric acid.
Thus, compound A must be an ester. Further, alcohol C gives acid B on oxidation with chromic acid. Thus, B and C must contain an equal number of carbon atoms.
Step 2:
Since compound A contains a total of 8 carbon atoms, each of B and C contain 4 carbon atoms.
Again, on dehydration, alcohol C gives but-1-ene. Therefore, C is of straight-chain and hence, it is butan-1-ol.
On oxidation, Butan-1-ol gives butanoic acid. Hence, acid B is butanoic acid. Hence, the ester with the molecular formula C8H16O2 is butyl butanoate.
The structure is as follows:
Step 2:
All the given reactions can be explained by the following equations as follows:
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