Basicity: To Resonance or Not to Resonance

Does resonance necessarily lead to a decrease in basicity?


Resonance or delocalization of electrons typically reduces the basicity of an organic compound since basicity means an ability to donate an electron pair according to Lewis. But…

Question:

Explain why Acetamide is neutral while aqueous solutions of Guanidine are nearly as basic as those of Sodium hydroxide. 

Solution infographic:



Click/tap to enlarge the image

EN= Electronegative, cA = Conjugate acid

Does it add up❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Wikipedia Contributors. Resonance (chemistry). Wikipedia. https://en.wikipedia.org/wiki/Resonance_(chemistry).

(2)    Acetamide. Wikipedia. https://en.wikipedia.org/wiki/Acetamide.
(3)    Guanidine. Wikipedia. https://en.wikipedia.org/wiki/Guanidine.

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