Hey Chad thanks again for this video. I just wanted to ask you for a quick clarification. So if the lone pairs on Nitrogen and Oxygen do NOT participate in resonance then those atoms are electron withdrawing, but if the lone pairs do participate in resonance then they are electron donating? Also for the halogens, would their lone pairs ever participate in resonance delocalization into a ring/ conjugated pi system?
Hello Andrew! Exactly right for the first half. When conjugated they can donate via resonance even though they are also inductively withdrawing; they are just more electron-donating than withdrawing so overall we consider them electron-donating. The halogens are also capable of being both electron-donating and withdrawing but are more electron-withdrawing. We'll visit this topic again in greater detail in chapter 18 here and even discuss the halogens specifically: th-cam.com/video/K05bDJMVgUI/w-d-xo.html Happy Studying!
@@ChadsPrep Thanks so much again for the clarification. I never thought I would be able to learn orgo in a way that would actually make sense until I came across your videos!
Thank you so much for the video! I just don't get one part,how do electron donating groups destabilize the conjugate base if they participate in resonance form? Isn't more resonance mean more stability?
Not necessarily! In the case of the withdrawing groups they are stabilizing the phenolate ion by pulling negative charge density away from the oxygen atom and essentially 'spreading' that negative charge out, making it a more stable conjugate base. Donating groups have the opposite effect and push more electron density into the ring, destabilizing it.
Great vid. Just a quick question - why would a benzene ring be electron donating? I was watching one of your vids I think in the aromatic ring stability chapter and it talked about how a benzene can stabilize a negative charge on a phenol's conj base, for instance. Like if a phenol was deprotonated and had O-, wouldn't the benzene resonance stabilize it? Would that still be electron donating or are these 2 different factors that counter each other or something. Thanks a ton!
We have both induction and resonance to consider when it comes to donating/withdrawing effects. Just as it stands, a Benzene ring is essentially another R group since it a ring of carbon and hydrogen, so it will be electron donating by induction. However, it does have a pi system which can be donating or withdrawing by resonance when we have positive or negative charges involved so it depends on the molecule in question in that case. Was the video talking about the benzene ring directly attached to the oxygen in phenol? Phenol has its own benzene ring which stabilizes the negative charge on the oxygen in a phenolate ion by resonance, but in this part of the video we are talking about the effect of a second benzene ring attached to phenol.
Yea in the vid, it was the benzene that's already a part of the phenol ring stabilizing the O-. But I see now, you meant a second, separate benzene ring's electron donating effects. I appreciate the response, this makes a lot of sense. Today I finished watching and making anki cards of all your orgo vids. Appreciate you, I've made like 1k cards of your orgo and gen chem playlists and do them everyday haha. I'll keep up and rewatch the vids as I get through UWorld problems, time to get to practice and taking MCAT prac exams. thanks@@ChadsPrep
Hello Neha! Not exactly the same thing. We view electron-donating groups as prosthetic groups that can be bonded to nucleophiles or electrophiles, or bases, or acids. When an electron-donating group is bonded to a nucleophile or base it increases the strength of that nucleophile or base, but has the opposite effect when bonded to an electrophile or acid. Electron-withdrawing groups have the opposite effect. So electron-donating and electron-withdrawing groups will not be the part of the molecule that is acting as the nucleophile, base, etc., but is a group that when attached modifies the reactivity of the nucleophile, base, etc. Hope this helps!
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Hey Chad thanks again for this video. I just wanted to ask you for a quick clarification. So if the lone pairs on Nitrogen and Oxygen do NOT participate in resonance then those atoms are electron withdrawing, but if the lone pairs do participate in resonance then they are electron donating? Also for the halogens, would their lone pairs ever participate in resonance delocalization into a ring/ conjugated pi system?
Hello Andrew! Exactly right for the first half. When conjugated they can donate via resonance even though they are also inductively withdrawing; they are just more electron-donating than withdrawing so overall we consider them electron-donating. The halogens are also capable of being both electron-donating and withdrawing but are more electron-withdrawing.
We'll visit this topic again in greater detail in chapter 18 here and even discuss the halogens specifically: th-cam.com/video/K05bDJMVgUI/w-d-xo.html
Happy Studying!
@@ChadsPrep Thanks so much again for the clarification. I never thought I would be able to learn orgo in a way that would actually make sense until I came across your videos!
Excellent - glad to hear it!
Thank you so much for the video! I just don't get one part,how do electron donating groups destabilize the conjugate base if they participate in resonance form? Isn't more resonance mean more stability?
Not necessarily! In the case of the withdrawing groups they are stabilizing the phenolate ion by pulling negative charge density away from the oxygen atom and essentially 'spreading' that negative charge out, making it a more stable conjugate base. Donating groups have the opposite effect and push more electron density into the ring, destabilizing it.
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Great vid.
Just a quick question - why would a benzene ring be electron donating? I was watching one of your vids I think in the aromatic ring stability chapter and it talked about how a benzene can stabilize a negative charge on a phenol's conj base, for instance. Like if a phenol was deprotonated and had O-, wouldn't the benzene resonance stabilize it? Would that still be electron donating or are these 2 different factors that counter each other or something.
Thanks a ton!
We have both induction and resonance to consider when it comes to donating/withdrawing effects. Just as it stands, a Benzene ring is essentially another R group since it a ring of carbon and hydrogen, so it will be electron donating by induction. However, it does have a pi system which can be donating or withdrawing by resonance when we have positive or negative charges involved so it depends on the molecule in question in that case. Was the video talking about the benzene ring directly attached to the oxygen in phenol? Phenol has its own benzene ring which stabilizes the negative charge on the oxygen in a phenolate ion by resonance, but in this part of the video we are talking about the effect of a second benzene ring attached to phenol.
Yea in the vid, it was the benzene that's already a part of the phenol ring stabilizing the O-. But I see now, you meant a second, separate benzene ring's electron donating effects.
I appreciate the response, this makes a lot of sense. Today I finished watching and making anki cards of all your orgo vids. Appreciate you, I've made like 1k cards of your orgo and gen chem playlists and do them everyday haha. I'll keep up and rewatch the vids as I get through UWorld problems, time to get to practice and taking MCAT prac exams. thanks@@ChadsPrep
Hi Chad, I was wondering if electron donating groups are the same as nucleophiles?
Hello Neha! Not exactly the same thing. We view electron-donating groups as prosthetic groups that can be bonded to nucleophiles or electrophiles, or bases, or acids. When an electron-donating group is bonded to a nucleophile or base it increases the strength of that nucleophile or base, but has the opposite effect when bonded to an electrophile or acid. Electron-withdrawing groups have the opposite effect. So electron-donating and electron-withdrawing groups will not be the part of the molecule that is acting as the nucleophile, base, etc., but is a group that when attached modifies the reactivity of the nucleophile, base, etc.
Hope this helps!
dude this is so helpful, awesome channel. subscribed.
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