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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. |
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Answer» Solution :(i) The organic COMPOUND (A) with molecular formula `C_(8)H_(16)O_(2)` UPON hydrolysis with dil. `H_(2)SO_(4)` gives carboxylic acid (B) and the alcohol (C ), therefore, (A) must be an ESTER. Further, oxidation of (C ) with chromic acid produces the acid (B), therefore, both the carboxylic acid (B) and the alcohol (C ) must CONTAIN the same number of carbon atoms. (ii) Since ester (A) contains eight carbon atoms, therefore, the carboxylic acid (B) and the alcohol (C )must contain four carbon atoms each. (iii) Since the alcohol (C ) on dehydration gives but -1- ene, (C ) must be a straight chain alcohol, i.e., butan -1- ol. (iv) If (C ) is butan -1- ol, then the acid (B) which it gives on oxidation must be butanoic acid and the ester (A) must be butyl butanoate. (v) The reaction can now be explained as follows : `underset(("Molecular formula "=C_(8)H_(16)O_(2)))underset("butylbutanoate (A)")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)C-OCH_(2)CH_(2)CH_(2)CH_(3))overset("Dil. "H_(2)SO_(4))underset("Hydrolysis")rarrunderset("Butanoic acid (B)")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)C-OH)+underset("Butan-1-ol (C)")(CH_(3)CH_(2)CH_(2)CH_(2)OH)` `underset("Butanoic acid (B)")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)C-OH)overset(CrO_(3)//CH_(3)COOH)underset("Oxidation")larrunderset("Butan -1- ol (C)")(CH_(3)CH_(2)CH_(2)OH) overset("Dehydration")underset((-H_(2)O))rarr underset("But -1- ene")(CH_(3)CH_(2)CH=CH_(2))` |
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