Question
Sun February 06, 2011 By: Rishita Gajbhiye

an organic compound (A)WITH MOLECULAR FORMULA C8H16O2 was hydrolysed with dil.sulphuric acid to give a carboxylic acid (B)& AN ALCOHOL(C).OXIDATION of (C) WITH CHROMIC acid produced (B).(c) on dehydration gives but-1-ene write equations for the reactions involved.pls explain how to do such questions?

Expert Reply
Mon February 07, 2011
Dear Student
 
Since, on hydration it has given an acid and an alcohol, it must be an ester.
 
As we know esters hydrolyse to produce mixture of acid and alcohol.
 
The alcohol undergoes dehyration and produces but-1-ene. This suggests that  the alcohol must be having four carbons and the OH group at position-1.
At position-1, since if the OH would have at position -2, we have obtained but-2-ene.
 
So, this is 1-butanol CH3CH2CH2CH2OH
 
Now we have one fragment of the ester (A), so, we can draw the structure of 
 
CH3CH2CH2COOCH2CH2CH2CH3
 
We hope that clarifies your query.
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Team
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