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Aldehydes, Ketones And Carboxylic Acids

Question
CBSEENCH12011345
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The relative reactivities of acyl compounds towards of nucleophilic substitution are in the order of 

  • Acyl chloride> Acid anhydride> Ester> Amide

  • Ester > Acyl chloride> Amide > Acid anhydride

  • Acid anhydride > Amide > Ester> Acyl chloride

  • Acyl chloride > Ester > Acid anhydride > Amide

Solution

A.

Acyl chloride> Acid anhydride> Ester> Amide

The ease of nucleophilic substitution is depended upon the nature of leaving the group. When the leaving tendency of a group in a compound is high, then the compound is more reactive towards nucleophilic substitution.
The nucleophilic acyl substitution is completed in two-step as shown below.

The reactivity of the compound may be explained on the basicity of the leaving group. A weaker base is a better leaving group. The basicity order is as:
Cl- < RCOO- < RO- < NH-2
Hence, the order of leaving tendency is

Cl- > RCOO- > RO-> NH-2
and therefore, the order of reactivity of acyl compounds is as:
Acyl chloride >Acid ayhdride > Ester > Amide

Some More Questions From Aldehydes, Ketones and Carboxylic Acids Chapter

Write the structures of the following compounds.
4-fluoro acetophenone.

Write the structures of the following reactions:

Write the structures of products of the following reactions:


    

Arrange the following compounds in increasing order of their boiling points:
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3.

Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions:    
Ethanal, Propanal, Propanone, Butanone.

Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions:    
Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.

Predict the products of the following reactions:

Predict the products of the following reactions:

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