you are a living legend and a real chad , CHAD!!! all love and support from an egyptian pharmacy student who finds this super helpful in understanding the O chem course .
I have got a question regarding to the last reaction in the video. Why not transforming the amide acid-catalyzed under heat and afterwards a direct acid-catalyzed reaction with the isopropanol? That would be one step less. Wouldn't it also work fine?
Hey Andreas! We totally could but since every step in the (Fisher Esterification) reaction is in equilibrium we would need to use an excess of the alcohol or carboxylic acid, or remove the water product in order to drive this to completion and obtain a good yield.
Just replied to the same question above: We totally could go this way but since every step in the reaction is in equilibrium we would need to use an excess of the alcohol or carboxylic acid, or remove the water product in order to drive this to completion and obtain a good yield.
Hello, Chad! You're a great teacher and I'm grateful that your videos really help me out here in my studies. I have a question tho'. Isn't it that aldehydes and ketones would react the least in this trend since the H and R groups connected to the carbonyl carbon are very weak bases? Thank you! :))
Hey JP! Thanks for your kind words :) Regarding your question - aldehydes and ketones don't react by this mechanism at all because they don't contain suitable leaving groups (weaker bases are better leaving groups as they are more stable on their own - so H- and R- are terrible leaving groups because they are strong bases), and instead they undergo nucleophillic addition reactions. Hope that clarifies!
That's been asked a few times here - We totally could go this way but since every step in the reaction is in equilibrium we would need to use an excess of the alcohol or carboxylic acid, or remove the water product in order to drive this to completion and obtain a good yield :)
Quick question - does the acid catalysis help the electrophiles get better leaving groups (by protonating them) while the base catalysis makes the nucleophiles get stronger by making them negative (deprotonating them). Thanks
Is this about a reaction in particular? Acid catalysis protonates the carbonyl oxygen (C=O) to form C=OH+ which makes the carbonyl carbon more electrophillic for attack by nucleophile. Basic catalysis does act on the nucleophile to make it stronger (more anionic), yes, as the reaction will not occur if the leaving group is a stronger base than the nucleophile.
Yea it was more for the carboxylic acid substitutions but also in general for any of these substitution reactions since they have a lot of the same common themes/patterns.But your response answered that so thanks, makes sense.
How could you explain all of this in that easily way in 30 minutes? My profisor takes 3 lectures every one for 3 hours and he didn't make me understand all of these
Hey Chad, on your second example at the end of the video, is it possible to skip the acid halide step and go directly to the ester from the carboxylic acid? I understand why it had to be converted down carboxylic acid from the amine, but why did we have to go all the way back up to halide instead of directly converting to an ester. Thanks :)
he replied in the comments above " every step in the (Fisher Esterification) reaction is in equilibrium we would need to use an excess of the alcohol or carboxylic acid, or remove the water product in order to drive this to completion and obtain a good yield"
