Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is:

  • Option 1)

    CH_{3}COOCH_{3}

  • Option 2)

    CH_{3}CONH_{2}

  • Option 3)

    CH_{3}COOCOCH_{3}

  • Option 4)

    CH_{3}COCl

 

Answers (1)
P Plabita

As we learnt in

Nucleophile -

Those e- rich  chemical species having capacity to attack e-deficient portion of substrate.

- wherein

Nucleophile must have complete octet and atleast one lone pair

 

 Lesser the electron density of acyl carbon atom, more is the susceptibility of a nucleophile attack. 

The Cl atom has strong -I effect and weakest + R effect. Because of the weak \pi bond between the small size C-atom and the large size Cl atom . Thus in CH3COCl, acyl  carbon has least electron denisty and hence more susceptible for nucleophilic attack.

 


Option 1)

CH_{3}COOCH_{3}

Incorrect

Option 2)

CH_{3}CONH_{2}

Incorrect

Option 3)

CH_{3}COOCOCH_{3}

Incorrect

Option 4)

CH_{3}COCl

Correct

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