Organic Chemistry · Chapter 8: Carboxylic Acids

Question

With increasing reactivity of carboxylic acids, there is a decrease in contribution of ____ from C.

Answer

With increasing reactivity of carboxylic acids, there is a decrease in contribution of resonance from C.
With increasing reactivity of carboxylic acids, there is a decrease in contribution of resonance from C.
Example: Here we see that acid halide, which is the most reactive carboxylic derivative participates in nucleophilic substitution in order to become other carboxylic derivatives, which are all less reactive than an acid halide.
Extra Note: Increasing frequency of the C=O absorption in the IR, as reactivity increases.
Carboxylic Derivatives Reactivity Order:
[1] Acid Halides → [2] Ester → [3] Carboxylic Acid → [4] Anhydride → [5] Ester.
In Summary: As the basicity of Z increases, the stability of RCOZ increases because of added resonance stabilization.

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