You mismatch these sizes they can't overlap as well. This resonance structure, we have a pi bond betweenĬarbon and chlorine, and if we draw the P orbital- carbon's in the second period, so we draw a P orbitalįor the second period, and the thing about chlorine,Ĭhlorine's in the third period so it has a bigger P orbital.
#REACTIVITY OF CARBOXYLIC ACID DERIVATIVES PLUS#
Possible resonance structure, once again a negative oneįormal charge on the oxygen, and a plus one formalĬharge on the chlorine. Possibility of resonance, I would move these electrons into here, and push those electrons Our carb needle carbon, and so does our chlorine. We know the oxygen withdraws some electron density from So we start with an acyl or acid chloride. And whichever one is going to win- we can think about thisīalance for helping us to determine the reactivity of our carboxylic acid derivatives. So we have these two competing effects, induction versus resonance. So resonance will decrease the reactivity of a carboxylic acid derivative.
![reactivity of carboxylic acid derivatives reactivity of carboxylic acid derivatives](https://image2.slideserve.com/4558093/reactions-of-carboxylic-acids-l.jpg)
Making it less electrophilic, and therefore making it less And if you're donating electron density, you're decreasing the To our carb needle carbon, that increases the electron density. Increasing the electron density from this lone pair of electrons And we would have a pi bond between our carbon and our Y substituent. Oxygen is going to have a negative one formal charge. When we draw our resonance structure we can see that our top So our Y substituent withĪ lone pair of electrons can donate some electron density And so induction increases the reactivity of carboxylic acid derivatives. So it's more electrophilic and better able to react
![reactivity of carboxylic acid derivatives reactivity of carboxylic acid derivatives](https://i.ytimg.com/vi/AuB3ftuZO44/hqdefault.jpg)
That makes our carb needleĬarbon more partially positive.
![reactivity of carboxylic acid derivatives reactivity of carboxylic acid derivatives](https://i.ytimg.com/vi/dBUizJ4gCEw/hqdefault.jpg)
We're withdrawing electron density from our carb needle carbon. So let's go ahead and writeĭown the first effect, the inductive effect. So that's going to withdrawĮven more electron density from our carb needle carbon. And for carboxylic acid derivatives our Y substituent is anĮlectronegative atom too. Some electron density away from our carb needle carbon, making it partially positive. We know that carb needlesĪre reactive because this oxygen is withdrawing Voiceover: Here we have a representative carboxylic acid derivative with this Y substituent hereīonded to the carb needle.