NaBH4, LiAlH4, DIBAL Reduction Mechanism, Carboxylic Acid, Acid Chloride, Ester, & Ketones
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- เผยแพร่เมื่อ 22 ส.ค. 2024
- This organic chemistry tutorial provides the reduction mechanism of ketones and acid chlorides to alcohols using NaBH4 and carboxylic acids and esters to alcohols using NaBH4 and esters to aldehydes using DIBAL. This video contains plenty of examples and practice problems.
Here is a list of topics:
1. Cyclohexanone to Cyclohexanol Reduction Mechanism Using NaBH4
2. Nucleophilic Addition Reactions
3. Hydride Ion Reduction & the Tetrahedral Intermediate
4. Aldehyde Reduction to a Primary Alcohol
5. Ketone Reduction to a Secondary Alcohol
6. NaBH4 Reduction of Acid Chlorides to Primary Alcohols
7. LiAlH4 Reduction Mechanism of Esters
8. Reducing Carboxylic Acids to Alcohols Using Lithium Aluminum Hydride
9. Amide Reduction to Amines LiAlH4 Mechanism
10. DiBAl reduction of esters to aldehydes
11. Selective Reduction - Ketones and Esters
12. Protecting Groups, Ethylene Glycol
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May the Lord grants you with many more years to live so that our next generation can pass chemistry easily
I am your lord.
I learned an entire semester's worth in 2 weeks because of you. You are the only one I can learn from
In india we learn this aged 16years. Sad situation, we study such things and get into universities which have no value on international lists
@@jaskaransinghsodhi3152 I am 16 years too and have to study this for oylmpiad
@@jaskaransinghsodhi3152 yo I'm preparing for jee too
@@allipse8224 🤝🤝🤝
@@jaskaransinghsodhi3152 America is VERY behind in public education 😂 I’m currently studying this in college!
I really appreciate the thoroughness of your videos. The way you look at mechanisms, note exceptions, and consider complex cases is why I recommend your videos to my students. Keep up the great work!
Ketone (LiALH4) - Secondary Alcohol
Aldehyde(LiALH4) -Primary alcohol
Ester with( Dibal-H)-Aldehyde -Primary alcohol
Carboxylic Acid (LiALH4 )- Aldehyde -Primary Alcohol
Amide - (LiALH4)-Imine-Primary Amine
Acid Chloride (LiALH4)- Aldehyde -Primary Alcohol
I was really worried of question related to LiAlH4 and NaBH4 ...but now its super easy😊😘
th-cam.com/video/FSdcvzqSD1I/w-d-xo.html
Reduction of organic compounds
I know I've said this to you before but you are gonna be the reason I understand this semester, thank you so much for what you do :)
You are the freakin' MAN.
Organic chemistry is easy.... when it is explained the way you do 💆🏼💁🏼🤓
I can't believe that 17mins into this video and I already understood reduction mechanism.....you are the man
I have my exam on ketone/aldehyde reactions, organometallics, and nitriles tomorrow. Bless you sir
AND imine and enamine formation/hydrolysis😭gotta make sure you have a video for that real quick
So question, does that mean all protonation is a form of reduction too? Since hydrogens added to a molecule means reduction?
EDIT: Actually, now that I think of it; reduction means the gain of electrons. Protons H+ don't have any electrons to bring with them, so then it wouldn't be a form of reduction unless the hydrogen was acting as a nucleophile with a partial negative charge, correct?
this was an entire lecture for me that i didnt understand in just over an hour. in 38 minutes you clearly and concisely closed this out for me. Thank you!
The clarity in explanation of mechanisms is the best one can get .
Man your videos are really really good, even better than the explanation that some teachers give. Thank you!
2:50 reduction of ketone(cyclohexanol) using nabh4
5:30 reduction of acyl chloride using nabh4
What is reduced when a mountain is made in emergent reality?
Amazing. You explain things so concisely and without the bloat that my class has. Thank you.
very nice and comprehensive lectures of organic chemistry
You make this so simple, I wish I had your videos for all my classes😭
instead of H3O use ethanol, it donates the proton from the hydroxide group then bonds with NaBrH3 to form NaBrH3OCH2CH3 as long as the ethanol if quite dry it shouldn't react.
Thank you so much. Will try to contribute to your patreon whenever I can because you're a brain saver and truly deserve the appreciation..
Absolute legend (God bless you🙏🏾)
Watching this during my first mental breakdown of the semester because teachers don't like to test over things they actually teach us 👍
thank you... great explanation!!! you make the concepts of organic chemistry easy to me
Oh my gosh why didn't I find you sooner. Bless you and your work! Thank you
This is your first video that I am watching and you are just great!!!👌
excellent ....brilliant.....you make organic chemistry so simple
you are absolute compltet teacher of the world pure chemist long life thank you very much dear!!!
You are doing the lord's work. I think I can actually pass o chem 2 thanks to your videos.
The video I needed before exam!
This was so helpful, I can't even explain! Thanks for helping me in my second sem of msc. 😇
Excellent videos. Keep it coming.
you are literally my hero right now, THANK YOU SO MUCH!!!
Great explanation. I wish in America we were exposed to this in highschool...
The explanation was perfect. Thank you very much.👌
Thank you very much for the range of examples of the detailed explanation！
Will the leaving group O-AlH2 interrupt the reactions at 28:31？
Putting millions of future scienctists in you hand only.....you work is a gem and voters to politicians.🥰
The DIBAL-H reaction mechanism is incorrect. DIBAL-H is very electron-deficient because of the aluminum's empty 3p orbital. Instead, it acts as the Lewis acid instead of the nucleophile.
You always save my ass before every exams.....may God bless you abundantly
you are the boss and savior.
I found this video accidentally although it was a topic i was desperately searching for yesterday im rly lucky to find this on time thank u so much
In reduction of carboxylic acid by LiAlH4, after 1st of acid base rxn ...Li should attach to the O atom having -ve charge......is it also correct method to proceed?
Thanks for you're well and indeed explanation
I don't know about you and me, but this guy is DEFINITELY going to heaven for all the souls he saved on the night before a test.
Why is the oxygen reforming a double bond again to kick out the CL.... Why can't the H3O+ just react with it once and for all
35:00 Can't we use Diborane to reduce only the ketone group and not the water group?
Think you so much sir the methods is easy and the knowledge is more
Amazing work my friend!
Much appreciated!!
Thanks paAl! Great explanations
Amazing as always!!!! Thank you so much!!!
In the reaction of reduction of the carboxylic acid, when H2 left as a gas, you didn't need to flip the dbl bonded oxygen around with the single one. They resonate anyway and both oxygens share that negative charge equally. Good video however. Really good explanations !
So is dibal h actually tert butyl aluminium hydride?
You're. The. BEST!
Why the boron ion is needed for lihb4 to exist ? Why not chlorine ? Lithium chlorohydride for example ؟
hey does someone know what is the mechanism for carboxylic acid with LiAlH4?
think you so much your videos are excelents
i love you so much
anybody get what water does in the DIBALH mechanism?
Lithium aluminum is more reactive why ? Because al has +3 charge ?
awesome explanation👌👌👌👍👍👍👍✌️
Thank you so much for these videos!
Thanks so much for this
But lol
Him: lithium tert-butoxy
Subtitles: lithium to boot oxy
Thank you once again.
God bless your soul
Lol f***
Use of alcoholic solvent not shown????? Is it ryt machanism
alchohlic? damn ur to drunk
great explanation thank you
Really thank you very much .you save us
The mechanism of the reduction of the amide into the amine is not right since you need only 1mol of LiAlH4 and the reaction can be done in a water free environment
This is amazing,thanks for sharing
i want some more detail about protection group
as... how to protect alcohol and several other functional groups...
Sir can u please help me by telling what’s the meaning of reducing hydrogen. ...I have heard of this term many times but dint cleared yet ...hopefully you will reply to my comment
Reducing hydrogen means , to reduce the other by giving the electron so it become oxidized itself and reduce the other
in 5:09 you didn't show the coordinate bond in hydronium ion
Thank you thank you so much❤
May live long
thank you so much!!!!
Why hydrogens in alh3- are nucleophilic and hydrogens in alh3 are not nucleophilic can anyone explain the reason
I'm binging your videos rn
How can both the amide and AlH4- lose H+? @25:10?
AlH4 loses H-
So at 25 minutes he says the Aluminum will grab a Hydrogen from the Nitrogen (because they're acidic) and then turns around and says the aluminum now has 3 hydrogens.... So it grabbed one and lost two????
My finals savior
You are amaizing ❤️
Can you pls put and explain all organic reactions for university students chemists 🥺
I'm confused with the carboxylic acid reduction... One H from the LiAlH acted as base and deprotonised the carboxylic acid.. When the aldehyde was formed why wasn't it also deprotonised but this time the H from LiAH attacked the carbonyl group 😟
In my textbook and on Khan Academy they have a different mechanism for LiAlH4 Reduction with Carboxylic Acids and Esters:
Basically, there is a partial negative charge on the Oxygen which is double bonded to the alpha Carbon (due to Oxygen being more EN than Carbon), thus leading to a partial positive charge on the alpha Carbon.
1. The pi bond between the Carbon and the Oxygen breaks and the electrons move onto the Oxygen forming O-. At the same time, the Hydrogen from the LiAlH4 then acts as a nucleophile and attacks the Carbon.
2. The extra pair of electrons on the Oxygen (O-) reform the pi bond, meaning that there are five bonds to the Carbon which is not possible. This forces the bond between the Carbon and the single bonded Oxygen to break. Now we have an aldehyde.
(3. We then perform the normal Aldehyde reduction with the excess LiAlH4 to get alcohol - I'm assuming you know this part).
NB! The single bonded carbon will form OH- (hydroxide ion) in Carboxylic Acids so this can be ignored, but Esters will form O-R which will react with the H2O/H+ to form another alcohol HO-R (where R is some carbon chain).
@@MrDSimba so do we use his mechanism or this one? lol
Initially you said we can't reduce aldehydes with LiAlH4 but at 23:00 you are doing the exact same thing!
quantised he didn’t say That
How does this man know so much about everything
so useful and well explained !! i have a question : is NaBH4 strong enough to an ester to an aldehyde ? thank you !
Thank you so much
sir ur audio quality is very low ,it is very diffcult to hear ,plzzz sir upgrade it
is it possible that there is a reduction of alkane?
NO!! There is no room to accommodate any more Hydrogen!!
I guess u can have ions but that's it
22:220 ok my brain stops here
omg same
My man carries millions of people for free
9:16
thank u
Why Li did not coordinate?
Its purpose is mainly that of a proton Carrier. however, in solution, it will orientate itself close to negatively charged atoms to prevent a nucleophilic attack.
Ethylene glycol will turn the ketone into a what, please?
Hakeshi Wakuro it will convert alcohol into cyclic kital
Cohol
your drawings are so funny 31:08
You are best
I really need a help pls help me
Book name please sir
I’m in love with you sir
JG, I truly bow to your greatness. However, NaBH4 does not reduce acid chlorides. In fact, it is unreactive in all the carbonyl-based functional group nucleophilic substitutions. It reduces ketones and aldehydes just fine though. Again, no disrespect meant; I watch tons of your science and math videos.