thanks so much chad ! i really like the way you explain those reactions, it makes it super easy to understand. it really helps prep for the national chemistry olympiad !
Hey! So acid-catalyzed ester hydrolysis is a reversible reaction and would be favored when the ester is heated under reflux with dilute acid, in which case the hydrolysis of ester in this reaction's conditions isn't super favorable.
Ethoxide is definitely not a good leaving group. You might even consider it close to the worst possible leaving group...but the key word is possible. If you look at video 20.2 on Nucleophilic Acyl Substitution (th-cam.com/video/3oaewJVZGt4/w-d-xo.html) the relative reactivity of carboxylic acid derivatives is discussed and one way of evaluating the relative reactivities is by ranking leaving groups. Acid chlorides are very reactive as they have a good leaving group (Cl). Acid anhydrides are the next most reactive as they have a decent leaving group being a resonance-stabilized carboxylate ion. But from there you see a significant reduction in reactivity as you look at esters next as alkoxide ions, being strong bases, are not great leaving groups. But with a strong enough nucleophile, they can function as leaving groups. Hope this helps!
Lithium Diisopropylamide. I cover it in detail in the first lesson in this chapter explaining how strong a base it is and how it is often used to deprotonate the alpha carbon. Hope this helps!
Bruhhh your the goat. Obviously not as in depth as my university professors but you simplified the main points to look out for. Thank you so much
Glad the video helped you - Happy Studying!
How are your classes going?
Litterally a life saver. I have been cramming for finals and your videos help so much. Thank you
You are welcome, Tabatha - good luck on your finals!
I know it's been two years, but how did your finals go?
thanks so much chad ! i really like the way you explain those reactions, it makes it super easy to understand. it really helps prep for the national chemistry olympiad !
Hope you do well!
How's the prep going, or did the olympiad already take place?
I love your videos. Omg I really love your shirt, may the LORD bless you more abundantly.
Thank you - and to you as well.
yesss that shirt though!!!!
😀
good job sir
Thank you
Thanks
best video
Thank you!
Nice video sir
Thanks!
I'm just curious what is that curved number 2 under Self-Claisen and left of the compound at the start of the video?
Hi chad. I'm wondering why when you add H3O+ at the end of the reaction to protonate the alpha carbon, the ester doesn't undergo hydrolysis?
Also thanks for your videos you're helping me study for my final !!!
Hey! So acid-catalyzed ester hydrolysis is a reversible reaction and would be favored when the ester is heated under reflux with dilute acid, in which case the hydrolysis of ester in this reaction's conditions isn't super favorable.
@@dayoogunlana5831 Did you already take your final, and if so, how'd it go?
This is brilliant, thank you, but why has ethoxide all of a sudden become a good leaving group (4:20)?
Ethoxide is definitely not a good leaving group. You might even consider it close to the worst possible leaving group...but the key word is possible. If you look at video 20.2 on Nucleophilic Acyl Substitution (th-cam.com/video/3oaewJVZGt4/w-d-xo.html) the relative reactivity of carboxylic acid derivatives is discussed and one way of evaluating the relative reactivities is by ranking leaving groups. Acid chlorides are very reactive as they have a good leaving group (Cl). Acid anhydrides are the next most reactive as they have a decent leaving group being a resonance-stabilized carboxylate ion. But from there you see a significant reduction in reactivity as you look at esters next as alkoxide ions, being strong bases, are not great leaving groups. But with a strong enough nucleophile, they can function as leaving groups. Hope this helps!
That was a really good point!
Can someone tell me what does LDA stand for???
Lithium Diisopropylamide. I cover it in detail in the first lesson in this chapter explaining how strong a base it is and how it is often used to deprotonate the alpha carbon.
Hope this helps!
@@ChadsPrep Thanks I was looking into aldol condense reaction and didnt come across that lesson
Did you watch 21.5b? th-cam.com/video/BTYN9AkPwE4/w-d-xo.html
@@ChadsPrep yup i did
❤
Thx!
I always get Claisen condensations confused with Claussen pickles.
Do you also imagine a stork saying, "Now that's a good reaction" ?
@@ChadsPrep I didn't, but now that you told me that, perhaps I will...
@@PunmasterSTP 😁 😁 😁