Linked Questions

By applying the logic that phenol exists in enol form rather than keto form as it attains aromatic character, why is it not the case in coumarin?

I am quoting a rule on resonance from Organic Chemistry by T.W. Graham Solomons, Craig B. Fryhle, 12th edition, page 25. Structures in which all the atoms have a complete valence shell of ...

The linked answers do attempt to clarify on 'stability' but I wanted an answer with specific connection to resonance. For example, the ethanoate ion can exist in many forms but, as we know from data,...

According to my coaching module the first structure is more stable. Why is this so? I feel both must be approximately equally stable since negative charge is on oxygen in both cases. Would someone ...

Does the existence of resonance structures always translate as stability? I've been taught that resonance structures generally "spread out" charge in order to compensate for deficiency or excess of ...

I'm trying to work out whether methylphenylsulfoxide is a chiral molecule. It is my understanding that the sulfur uses sp2 hybridised orbitals. Why is this? The central sulfur atom is bound to 3 ...

Numerous online references say that $\ce{SCN-}$ has two resonance structures: I am wondering why this structure is not also possible? I expect structure 3 to be rare because of the high formal ...

VSEPR theory correctly predicts the shapes of many symmetry-broken molecules such as $\ce{H2O}$ and $\ce{NH3}$. Take $\ce{NH3}$ for example. In VSEPR theory, the nitrogen atom is (approximately) at ...

There is a specific part of the biosynthesis of terpenes that makes me confused: According to this mechanism, the double bond of the isopentenyl pyrophosphate attacks the primary carbocation, when it ...

Consider the "true" resonance structure of $\ce{CO3^2-}$: The bottom diagram leaves out the 2 lone pairs, so 4 electrons disappeared in the bottom image as compared to the top one. Are these ...

A question on the 1996 AP Chemistry Free Response asks: The $\ce{N-O}$ bonds in the $\ce{NO2-}$ ion are equal in length, whereas they are unequal in $\ce{HNO2}$. Explain. Since the nitrogen ...

While studying several organic mechanisms (high school level), I came to an interesting generalization. I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then ...

Can someone please explain why the resonance structures of fulvene 1 is non-aromatic and 2 is anti-aromatic? Why is fulvene non-aromatic, even though it has $4\pi$-electrons and no $\mathrm{sp^3}$ ...

Consider: I found these rearrangements, but I could not understand what the mechanism is behind this. When I searched on the Internet I found the Wikipedia page Di-pi-methane rearrangement.

We say that hybrid structure is real. It has distinct properties as compared to its Resonating Structure. Is it because that all the experiments we carry out are on a sample, lots of molecules are ...