20.2 Nucleophilic Acyl Substitution | Organic Chemistry

[@hemawbs88]

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 .

[@ChadsPrep]

Thank you - glad the channel is helping you!

[@MaxVangogh7]

The chart is super helpful, I wish my professor taught it like this. Thank you for always saving my grades!

[@ChadsPrep]

Glad the channel is helping you.

[@hiranthini1]

Excellent method of teaching, I really liked the way you show the different reactions.

[@ChadsPrep]

Thank you!

[@NoorNoor-pf5id]

Passed orgo 1 last semester with B- and now taking orgo 2 and my first person to learn things from is you. Much love and respect to you

[@ChadsPrep]

Great to hear this! Keep up the good work and love and respect right back at you :)

[@abigailbui5753]

100% my favorite video of yours. The diagram and delivery was genius. thanks again!

[@ChadsPrep]

Glad you liked it!

[@strugglingcollegestudent]

I love this chart because I know there's no way I could memorize all the reactions for ochem this makes the patterns very clear!

[@ChadsPrep]

Glad it helps - Happy Studying!

[@gizachewmulualem]

HI GUIES

[@ChadsPrep]

@@gizachewmulualem Welcome to the channel.

[@heatherbland5597]

This is the best video of yours I’ve seen. Makes the pattern so clear!

[@ChadsPrep]

Glad you think so!

[@jadeluu6061]

this is crazy wow, chart changed my life

[@ChadsPrep]

Great!

[@jaydenallegakoen9974]

This is one of the best explanations ever bro. thanks so much!

[@ChadsPrep]

You're welcome and Thank You!

[@BruceWayne-i2n]

Just spent an hour and a half making anki cards on the chart 😆 appreciate the effort and succinctness of this video. just so well explained

[@ChadsPrep]

Glad it helped!

[@laura5878]

I worship you.

[@ChadsPrep]

As long as the channel is helping you, I'm pleased - Happy Studying!

[@nilsnickname4455]

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?

[@mirjam9365]

I was thinking the same thing

[@ImAzer]

Hey Chad, quick question, in the last example, couldn't we go directly from carboxylic acid to ester with R'OH/H+?

[@ChadsPrep]

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.

[@belalsalama4995]

for the last example, couldn't we go directly from carboxylic acid to ester with R'OH/H+

[@equityeyewear1987]

Yes, I had that question as well

[@madisenw.4059]

I also had that question when we walked through the last example. I would think so? It'd be one less step.

[@mallorythompson3365]

Maybe that would just give the corresponding ester rather than the specific product we need? I was wondering that as well.

[@ChadsPrep]

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.

[@abdoulazizdabo9064]

Thank you 🙏🏾

[@ChadsPrep]

You are so welcome

[@dheranshahi4741]

Mans doing gods work

[@ChadsPrep]

Thanks!

[@jpbolivar9995]

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! :))

[@ChadsPrep]

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!

[@dwrans6147]

thank you so much!! Your videos are really helpful :))

[@ChadsPrep]

Glad you like them!

[@forlornhauntedghost]

You're amazing!

[@ChadsPrep]

Thank you

[@bboir]

I am not sure if you will see this message. In the last example why didnt you use excess H3O+ to go from carboxylic acid to ester?

[@ChadsPrep]

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 :)

[@BruceWayne-i2n]

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

[@ChadsPrep]

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.

[@BruceWayne-i2n]

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.

[@ChadsPrep]

Great to hear and you are welcome :)

[@ItsMe-dj6pl]

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

[@ChadsPrep]

Glad you found it so helpful :)

[@SM-gc2tx]

absolute chad

[@ChadsPrep]

Happy Studying!

[@Yamikani-e5w]

Thank you Bald guy😊

[@ChadsPrep]

You're welcome, Person of Unknown Follicle Quantity.

[@BruteDuke]

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 :)

[@SM-gc2tx]

I was wondering the same thing

[@CCai-yr5gr]

But you just said caboxylic acid can turn into ester with acid catalyze, wht did you have to go back to acid halide???

[@felixm2586]

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"

[@sciencenerd7639]

wow!

[@ChadsPrep]

thanks!