It is tempting (and very wrong!) to think that these resonance forms are in “equilibrium” between each other. Here’s an important point about resonance forms. Remember That Resonance Structures Are Not In Equilibrium With Each Other – They Represent Contributions To An Overall Resonance “Hybrid” There are three “legal” ways to move electrons using curved arrows: from pi bond to lone pair, from lone pair to pi bond, and from pi bond to pi bond:Ģ. How can we “find” resonance forms for a given molecule? It’s possible to do it through trial-and-error, but one surefire way is to do so is to apply the curved arrow formalism, which is a way of depicting the “movement” of electrons. Therefore, in order to understand electron density on a molecule where pi bonds are present, we must first understand the importance of its various resonance forms. However if multiple bonds (π bonds) are present, then we start to run into a little problem: there can be multiple ways to distribute electrons on the same molecule (i.e. One of the key skills in analyzing the reactivity of a molecule is to be able to figure out where the electrons are.Īs I wrote here, if we’re dealing with single bonds, it’s a relatively straightforward matter of figuring out the differences in electronegativities. Recall The Three “Legal” Electron-Pushing Arrow “Moves” Used For Interconverting Resonance StructuresĪfter all these posts about resonance, I thought it would be good to have a post summarizing what’s been discussed so far. Quiz Yourself! (On Evaluating Resonance Structures)ġ.A Second Application Of Resonance: “Pi Acceptors”.An Application Of Resonance: “Pi Donation”.Rule #4: Place Any Empty Octets On the Atoms Best Able To Stabilize Them (i.e.Rule #3: Place Negative Charges On The Atom Best Able To Stabilize It (i.e.Rule #2: Full Octets Are Preferable To Empty Octets (And Never, Ever Have Empty Octets On Oxygen or Nitrogen!).Rule #1: Neutral Resonance Structures Are More “Important” Than Charged Resonance Structures.So How Do We Evaluate How “Important” Each One Is? Not All Resonance Forms Are Of Equal Significance. Remember That Resonance Structures Are Not In Equilibrium With Each Other – They Represent Contributions To An Overall Resonance “Hybrid”.Recall The Three “Legal” Electron-Pushing Arrow “Moves” Used For Interconverting Resonance Structures.Today, let’s summarize everything we’ve learned about resonance structures in this unit. Rule #4: How stable are the positive charges?.Rule #3: How stable are the negative charges?.So how do we evaluate how “important” each resonance structure is?Īs we’ve seen in previous posts, four key factors that determine the importance of resonance structures in organic chemistry are: Not all resonance forms are of equal importance. The Four Key Factors In Evaluating Resonance Structures
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