Nucleophilic Acyl Substitution Reaction Mechanism - Carboxylic Acid Derivatives, Organic Chemistry
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- Опубликовано: 9 июл 2024
- This organic chemistry video tutorial discusses the reaction mechanism of nucleophilic acyl substitution reactions also known as carboxylic acid derivative reactions. This video contains plenty of examples and practice problems.
Here is a list of topics:
1. Acid Chloride Reactions
2. Hydrolysis of Acid Chlorides - Formation of Carboxylic Acids
3. Formation of Esters Using an Acid Chloride and an Alcohol
4. Amide Formation Reactions Using an Amine and an Acid Chloride
5. Tetrahedral Intermediate of Nucleophilic Acyl Substitution Reactions
6. How to predict the major product of a carboxylic acid derivative reaction
7. Acid Catalyzed Ester Hydrolysis Reaction Mechanism
8. Base Promoted Ester Hydrolysis
9. Base Promoted Hydrolysis of Amides
10. Amide Formation Reactions
11. Amide Hydrolysis Reaction Mechanism
12. Ester Formation Reaction Mechanism
13. Lactone Formation Synthesis Reaction
14. Acid Anhydride Formation Reaction Mechanism
15. Amide to Nitrile Mechanism Using SOCl2
16. Dehydration of Amides to Nitriles
17. Lactam Hydrolysis - Cyclic Amides
18. Cyclic Anhydride Formation
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Watching this 2 hours before my exam in hopes of not completely failing
Lol I was exact same
how did you get on 😂
😂 me
How did your test go??
Same
You're my homie. Thank God for you
fam, your videos are great. just a humble request, would you mind naming the starting reactants and the products so we can get in the habit of naming things. even though that isnt the main focus of the video.
Thank you!
damn dude save some girls for the rest of us. absoulute chadster organic master
Thanks! 💕
great video
life saver
1) Thank you so much for the video your work is much appreciated.
2) You did the mechanism for the third one incorrectly as you did say in the beginning that HCl is produced but in the mechanism you had the HOCH3 take the proton and not Cl-.
for point 2, both can happen
الله نور السماوات والأرض
Why don't the halides in various reactions come back after leaving and perform the final deprotonation? I've seen some reactions use Pyradine to prevent HCL, etc from forming, but this is inconsistent. Is there a rule around this or some way to know when the halide will deprotonate or not?
Was wondering same
So HCl is a very strong acid, in an aqueous solution it will completely dissociate. It's also not something that will really like to form because nature doesn't like forming strong acids as products. Adding pyridine will give somewhere for that acidic proton to go and also serve as a counter-ion for the chlorine anion. That will make this entire reaction go a lot quicker. However, if you don't do this in pyridine, you may be able to write the products as an equilibrium with carboxylic acid + chlorine atom carboxylate and hydrochloric acid. Personally, I would write this as favoring the reactants.
I am also an orgo student so take my advice with a grain of salt.
In a basic solution with pyridine, you'll probably end up with the carboxylate salt and pyridinium chloride. Depending on the pH, you may need to add a dilute acid to get the carboxylic acid.
At 6:36 why wouldn’t the Cl come back and deprotonate the oxygen? Wouldn’t it form the stronger acid/more favorable?
A stronger acid is the opposite of more favorable, strong acids have weak conjugate bases (that are stable) and therefore willing to donate their proton more than other acids (to get to that more stable conjugate base). So it will never be favorable to form a strong acid, rather it's favorable for the strong acid to protonate another species and become the weak, stable conjugate base (Cl-)
It is theoretically possible for that chloride ion to bump into that proton and grab it, but that forms HCl, which will be very good at getting rid of that proton as soon as it gets its hand on it. When we do these mechanisms we kind of just have to look at the bigger picture.
20:28 how do you know which bond to cleave when predicting the product?
God
Please help me. Why lauric acid can dissolve in concentrated H2so4?
Happy Chemist no
the most confusing unit of organic chem so far. it feels like youre pulling a rabbit out of hat when things randomly come in and out of the picture to protonate or deprotonate. some times its water acting as a base, some times the anion of a leaving group comes back around ect. god I cant wait until this torture is over
I feel you man. It feels like an impossible maze