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Q. Order of hydrolysis for the following : (I) $ RCOCl $ (II) $ RCOOR $ (III) $ RCONH_{2}$ (IV) $(RCO)_{2}O $

Delhi UMET/DPMTDelhi UMET/DPMT 2005Aldehydes Ketones and Carboxylic Acids

Solution:

(i) Acid chlorides is most reactive and is hydrolysed slowly by water as follows:
$CH _{3} COCl + H _{2} O \rightarrow CH _{3} COOH + HCl$
(ii) Acid anhydrides are less reactive than acid chlorides.
They are hydrolysed slowly by water.
$\left( CH _{3} CO \right)_{2} O + H _{2} O \rightarrow 2 CH _{3} COOH$
(iii) Ester are hydrolysed slowly by water in presence of acid or alkali.
$RCOOR+H_{2} ORCOO H+ROH$
(iv) Amides are hydrolysed very slowly by water.
$R-\overset{\underset{||}{O}}{C} - NH _{2} + H _{2} O \xrightarrow{ H ^{+}} RCOOH + NH _{3}$
$\therefore $ The correct order of hydrolysis is:
$RCOCl > (RCO)_{2} O > RCOOR > RCONH_{2}$