Aldehydes Ketones Question 30
Question: Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
Options:
A) $ MeCOCl $
B) $ MeCHO $
C) $ MeCOOMe $
D) $ MeCOOCOMe $
Show Answer
Answer:
Correct Answer: A
Solution:
[a] More the magnitude of positive charge on the carbonyl carbon, higher will be its reactivity toward nucleophilic attack. $ CH_3-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-ClCH_3-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-HCH_3-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-OCOCH_3CH_3-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-OCH_3 $ Chlorine being more electron-withdrawing than O develops more positive charge on carbonyl carbon. The order of reactivity of the various carboxyl derivatives toward nucleophile is $ \underset{Mostreactive}{\mathop{RCOCl}}>RCHO>{{( RCO )}_2}O>\underset{Leastreactive}{\mathop{RCOOR}} $
BETA
