A trick for figuring out if a group is electron-donating or electron-withdrawing (except for halogens), and the chemical basis behind the trick. Discussion of how EDGs and EWGs affect electrophilic aromatic substitution.
You're correct, it wouldn't! But, I don't think a nitrosobenzene can actually participate in EAS. Nitrosobenzene is very reactive at the N=O group-it can undergo nucleophilic addition similar to a carbonyl AND the nitrogen lone pair can act as a nucleophile. However, there are (to my best knowledge, thanks for encouraging me to have a fun little literature search today) no reported EAS reactions of nitrosobenzenes. I'm thinking that the Lewis acidic conditions for EAS are not compatible with this group. The N=O group readily dimerizes, and I think a Lewis acid might promote that reaction well before EAS could occur (pubs.acs.org/doi/abs/10.1021/ja00827a021). I did find that someone asked this question in a problem that wound up on the internet (someone answered it on Chegg) but I'm not sure we need to worry too much about this group for EAS. Thanks so much for posting! I really enjoyed thinking about this one :)
Oh man-I must have missed it! I was only using Google Scholar because it was Sunday and I don't have SciFinder access off campus. Please post a reference for me! I have to see these conditions. :) Thank you!
Crazy this did not come up in any of my searches yesterday (I was using keyword nitrosobenzene, and this didn't get anything until I dropped the "benzene")! I just found a synthesis of a para-subs nitrosobenzene in "Science of Synthesis." Doesn't seem like an efficient reaction-have you done this in the lab? Thanks for teaching me something!! :)
Molecular Memory no I haven't done it in lab but I referred many books for this...!!! Your video really helped thanks alot and I can't teach I'm only 16 😛....just kidding!!
This is awesome! my lazy orgo professor keeps teaching half the material we need to actually understand stuff and then starts randomly talking about things she never bothered to explain. EWG and EDG are one of those examples and today she just started throwing those phrases into lecture out of nowhere.
I have never made a comment on a video before, although I have given thumbs up or down. EAS was kicking my butt and I was so frustrated not being able to figure it out. Thank you so much for this video........
THANK YOU for making this video. This trick really helped me. I REQUEST you to make more videos with tricks if you are wished to , but i really got benefited by this video.
Omg I freaking love you. Thank you so much for this video. I think I am only going to watch English content from now on for studying because these videos are so much more helpful than the German videos that are on RU-vid 😂
masha-Allah how can this amazing teacher explains this just within 8.09 minutes? omg you're so blessed..thanks a lot!! your video is very helpful. I wish you have a great day! I was like 'thank God, I met her'
Thank you for explaining the concept so clearly. However, can I ask about just a halogen bonded to the benzene? It’s electron donating (so ortho para directing) but yet it weakly deactivates the ring.
Been studying orgo chem on spare time (odd as that may sound) for the past couple of years. This video was very helpful providing an easy way to remember the EDG and EWG on Benzene rings. And in this subject, memory recall is very important. Thanks !
first you said that EWG is meta director but in your example (A) that was EWG but you show that is also para director if i say any wrong then please explain me that portion
If Y is more electronegative then Z it is electronwithdrawing group and if Z is more electronegative than Y then it is electrondonating group i think this is the right one
The oxygen wins here, and aldehydes are EWG. Hydrogen is less electronegative than carbon, but just slightly. Hydrocarbons are considered to be nonpolar, since the electronegativity difference between C and H is not very much. Thanks for a great question!
The directing effects are for EAS. However, this analysis will work to tell you if any group is electron donating or electron withdrawing. Thanks for watching and leaving me a question!
