How to Account for the Greater Reactivity of an Organic Compound toward Hydrolysis - Part 2

The stability due to some electronic effects is one of the most important things that matters in any organic reaction.


The inductive (I) effect and the mesomeric (M) (or resonance (R)) effect are two significant electronic effects in organics.

Question:

Arrange the following compounds in the decreasing order of their reactivities toward hydrolysis:



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Solution infographic:



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Sigma resonance, aka dancing resonance, which results from the overlap of the vacant p-orbital of the carbocation with the bent, partly sigma-like C-C bonds of the cyclopropyl (Cp) ring, allows the sigma bond's electron cloud to spread, effectively delocalizing the positive charge and relieving the ring's strain. This mechanism explains the exceptional stability of a carbocation adjacent to a Cp ring.

Interesting❓ Let Chemaficionado know at mychemistryhomework@gmail.com❗

References:

(1)    Inductive effect. Wikipedia. https://en.wikipedia.org/wiki/Inductive_effect.

(2)    Mesomeric effect. Wikipedia. https://en.wikipedia.org/wiki/Mesomeric_effect.

(3)    Know About Sigma Resonance Or Dancing Resonance - CG’s Chemistry Solutions. https://www.cgchemistrysolutions.co.in/dancing-or-sigma-resonance/‌

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