Hello Chad, I have a question according to the acid catalyzed 6 step mechanism of the imine formation. Why does the proton transfer not happen intramolecular? Why won't the quartenary ammonium ion give a proton direct to the geminal alkoxyd anion? Isn't it much faster and therefore more probable when molecules don't have to "find" each other?
Wouldn't an intramolecular reaction between the -ve charged O be more efficient to get rid of the nitrogens +ve charge by reacting with an excess hydrogen? @ 6:30 on the video, thanks.
That's a good observation but that the oxygen is too close to Nitrogen do that. My guess is that it could happen if N and O were beta to each other, or even farther on the same molecule.
Hello Chad, I guess, that your reaction mechanism isn't completey valid. You can't attack with the N-nucleophile before having protonated the carbonyl-oxygen atom. If you do so, the microscopic reversibility wouldn't be maintained. When you set up the reaction for the back reaction, i.e. for the imine hydrolysis, you will see, that it isn't possible to get a molecule with a positive charge on the nitrogen atom and a negative charge on the oxygene atom at the same time!
Lol, the pause at 21:51 was funny. Reminds me that even Chad has to stop and format his thoughts.
Thank you so much for the videos Chad!
You're welcome - glad you enjoy them!
This a great video on this topic, covered all the reactions.
Thank you so much.
Glad you enjoyed it, Samira!
شكرآ جزيلا♥️💓
؛Thank you💝
You're welcome :)
Thank you so much!
You're welcome!
Thank u,!!!!! 👩🏫
You are welcome, Fernanda!
Hello Chad,
I have a question according to the acid catalyzed 6 step mechanism of the imine formation.
Why does the proton transfer not happen intramolecular?
Why won't the quartenary ammonium ion give a proton direct to the geminal alkoxyd anion?
Isn't it much faster and therefore more probable when molecules don't have to "find" each other?
Hi Dactor
Why only primary amines can be formation the imines!
Me saying "Schiff base" until I figured it out LOL
👍 👍 👍
hahaha I still have not figured it out
Wouldn't an intramolecular reaction between the -ve charged O be more efficient to get rid of the nitrogens +ve charge by reacting with an excess hydrogen? @ 6:30 on the video, thanks.
That's a good observation but that the oxygen is too close to Nitrogen do that. My guess is that it could happen if N and O were beta to each other, or even farther on the same molecule.
@@peybak Thank you for the insight, sorry for the long response
@@weewaa592 No worries
What's your fav functional group?
hahaha i don't know what happened in 21:51 but it was funny specially in 1.5 speed
Normal or 1.5x - either way, a silly moment for all to enjoy!
Hello Chad,
I guess, that your reaction mechanism isn't completey valid.
You can't attack with the N-nucleophile before having protonated the carbonyl-oxygen atom.
If you do so, the microscopic reversibility wouldn't be maintained.
When you set up the reaction for the back reaction, i.e. for the imine hydrolysis, you will see, that it isn't possible to get a molecule with a positive charge on the nitrogen atom and a negative charge on the oxygene atom at the same time!
THATS A SCHIFF BASE