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Q.
Order of hydrolysis for the following: (I) $ RCOCl $ (II) $ RCOOR $ (III) $ RCON{{H}_{2}} $ (IV) $ {{(RCO)}_{2}}O $
MGIMS WardhaMGIMS Wardha 2006
Solution:
In acid derivatives acid chlorides is most reactive, it is vigorously hydrolysed by water. $ C{{H}_{3}}COCl+{{H}_{2}}O\xrightarrow{{}}C{{H}_{3}}COOH+HCl $ Acid anhydride is less reactive than acid chlorides. It is hydrolysed slowly by water. $ {{(C{{H}_{3}}CO)}_{2}}O+{{H}_{2}}O\xrightarrow{slow}2C{{H}_{3}}COOH $ The hydrolysis of ethyl acetate in boiling water is slow but in the presence of acid or alkali the reaction is fast. $ C{{H}_{3}}CO-O{{C}_{2}}{{H}_{5}}+{{H}_{2}}OC{{H}_{3}}COOH $ $ +{{C}_{2}}{{H}_{5}}OH $ Amides are hydrolysed by water very slowly. $ R-\overset{\begin{smallmatrix} O \\ || \end{smallmatrix}}{\mathop{C}}\,-N{{H}_{2}}+{{H}_{2}}O\xrightarrow{{{H}^{+}}}R-COOH+N{{H}_{3}} $ Thus, the correct order of hydrolysis is $ RCOCl>{{(RCO)}_{2}}O>RCOOR>RCON{{H}_{2}} $