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See, there are few things you should keep in mind while deciding comparative stability of resonance structures: Non-polar structures are more stable than dipolar. Resonance structures with a greater number of covalent bonds are more stable than those with lesser number. Thus, nonpolar structure of buta-1,3-diene is more stable than any other resonating ...

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About the molecule that you remember cited in your textbook, there's a study in ref.1. According to these authors: The delocalization of the C1-C2 and Cl-C3 electrons of spiro[2.4]hepta-4,6-diene (1a) and partial rehybridization at C1, C2, and C3 result in a contributing structure which is perhaps best represented as a $\pi$ complex (lb) of ...

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As you can see in this structure 3 equivalent resonance structures are possible by simple conjugation between negative charge and the π bond. Hence being covalent is not a condition for possible resonance even compounds with some ionic character can show resonance besides all compounds have some ionic and covalent nature both present. In the other options ...

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Deprotonation creates a negative charge on the phenolic oxygen. The better you can stabilise this charge, the more favored this process is going to be. You are right in saying that the charge can be stabilised by delocalisation in the aromatic ring. However, the electrons of the methoxy oxygen can also be delocalised in the ring (to a much lesser extend, of ...

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I wanted to add a perspective to this since this can be a contentious issue, and I would still say knowing whether a nitrogen is $sp^2$ or $sp^3$ hybridized is not straightforward. I was originally hoping to add this under this question specifically about aniline, but that question is now closed and marked as duplicate, with a link to this question. In a ...

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