The relative reactivities of acyl compounds towards 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
The Correct Option is A
Solution and Explanation
anhydride, ester and amide) RCO- group is same,
thus reactivity depends upon the nature of group Z
(i.e. Cl, $RCOO^-, R'O^-, NH_2^-$, etc.)
If group Z is a weak base, then it is a strong leaving
agent and its reactivity towards nucleophilic
substitution is high.
The order of basic nature of Z groups is
$\hspace10mm Cl^- < RCOO^- < R' O^- > NH_2^-$
Thus, order of reactivity is
$_{Acyl \, chloride \, \, \, \, \, Acid \, anhydride \, \, \, Ester}^{ \, \, \, \, RCOCI \, \, \, \, \, > \, \, \, \, \, (RCO)_2 O \, \, \, \, \, > RCOOR'} { \, \, \, \, \, \, \, \, Amide }^{>RCONH_2}$
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Concepts Used:
Aldehydes, Ketones, and Carboxylic Acids
Aldehydes, Ketones, and Carboxylic Acids are carbonyl compounds that contain a carbon-oxygen double bond. These organic compounds are very important in the field of organic chemistry and also have many industrial applications.
Aldehydes:
Aldehydes are organic compounds that have the functional group -CHO.
Preparation of Aldehydes
Acid chlorides are reduced to aldehydes with hydrogen in the presence of palladium catalyst spread on barium sulfate.
Ketones:
Ketones are organic compounds that have the functional group C=O and the structure R-(C=O)-R’.
Preparation of Ketones
Acid chlorides on reaction with dialkyl cadmium produce ketones. Dialkyl cadmium themselves are prepared from Grignard reagents.
Carboxylic Acid:
Carboxylic acids are organic compounds that contain a (C=O)OH group attached to an R group (where R refers to the remaining part of the molecule).
Preparation of Carboxylic Acids
Primary alcohols are readily oxidized to carboxylic acids with common oxidizing agents such as potassium permanganate in neutral acidic or alkaline media or by potassium dichromate and chromium trioxide in acidic media.