NaBH4, LiAlH4, DIBAL Reduction Mechanism, Carboxylic Acid, Acid Chloride, Ester, & Ketones

Подписаться 8 млн

Просмотров 504 тыс.

50% 1

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
Organic Chemistry PDF Worksheets: www.video-tuto...
Organic Chemistry Exam 1 Playlist: bit.ly/3kJnNXU
Organic Chemistry 1 Exam 2 Playlist: bit.ly/3PKEApB
List of Extended Organic Chemistry Videos: • List of Organic Chemis...
________________________________________________________________________________________________
Organic Chemistry - Basic Introduction: • Organic Chemistry - Ba...
How To Draw Lewis Structures: • Organic Chemistry - Ho...
Functional Groups Review: • Functional Groups
How To Calculate Formal Charge: • How To Calculate The F...
Valence Bond Theory: • Valence Bond Theory & ...
Hybridization of Atomic Orbitals: • Hybridization of Atomi...
Bond Length & Bond Strength: • Bond Strength and Bond...
Resonance Structures: • Resonance Structures
Acids and Bases - Introduction: • Acids and Bases - Basi...
pKa Values of Acids: • pKa Values of Acids - ...
Constitutional Isomers: • Constitutional Isomers
IUPAC Nomenclature of Alkanes: • IUPAC Nomenclature of ...
Naming Bicyclic Compounds: • Naming Bicyclic Compounds
Boiling Point of Organic Compounds: • Boiling Point of Organ...
Newman Projections: • Newman Projections
Chair Conformations: • Chair Conformation and...
Organic Chemistry Exam 1 Review: • Organic Chemistry Exam...
Organic Chemistry Exam 1 Questions: • Organic Chemistry Exam...
Stereochemistry R/S Configuration: • Stereochemistry - R S ...
Optical Activity & Specific Rotation: • Optical Activity - Spe...
SN1, SN2, E1, E2 Reaction Mechanisms: • SN2 SN1 E1 E2 Reaction...
SN2 Reaction Mechanisms: • SN2 Reaction Mechanisms
SN1 Reaction Mechanisms: • SN1 Reaction Mechanism
SN1, SN2, E1, E2 - Practice Test: • SN1 SN2 E1 E2 Reaction...
Naming Alkenes - E/Z System: • Naming Alkenes Using E...
Index of Hydrogen Deficiency: • Degree of Unsaturation...
Alkene Reactions Review: • Alkene Reactions
Alkyne Reactions Review: • Alkyne Reactions
Organic Chemistry Exam 2 Review: • Organic Chemistry 1 Ex...
Organic Chemistry Exam 2 Questions: • Organic Chemistry 1 Ex...
Alcohol Reactions: • Alcohol Reactions - HB...
Free Radical Reactions: • Free Radical Reactions
Organic Chemistry Reactions Summary: • Organic Chemistry Reac...
Organic Chemistry 1 Final Exam Review: • Organic Chemistry 1 Fi...
Organic Chemistry 2 Final Exam Review: • Organic Chemistry 2 Fi...

Опубликовано:

13 окт 2024

Ссылка:

Скачать:

Готовим ссылку...

Добавить в:

Мой плейлист

Посмотреть позже

Комментарии : 159

@TheOrganicChemistryTutor 9 месяцев назад

Final Exams and Video Playlists: www.video-tutor.net/

@sfisotheartistgumbi1240 3 года назад

May the Lord grants you with many more years to live so that our next generation can pass chemistry easily

@kylitrixgames4980 9 месяцев назад

I am your lord.

@Michelle-rv9ns 5 лет назад

I learned an entire semester's worth in 2 weeks because of you. You are the only one I can learn from

@jaskaransinghsodhi3152 3 года назад

In india we learn this aged 16years. Sad situation, we study such things and get into universities which have no value on international lists

@浅野凛-s2x 3 года назад

@@jaskaransinghsodhi3152 I am 16 years too and have to study this for oylmpiad

@allipse8224 3 года назад

@@jaskaransinghsodhi3152 yo I'm preparing for jee too

@Indscofmaths 2 года назад

@@allipse8224 🤝🤝🤝

@HungUpOnADream1122 Год назад

@@jaskaransinghsodhi3152 America is VERY behind in public education 😂 I’m currently studying this in college!

@10gnanapandianp95 2 года назад

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

@thecasualchemist1161 3 года назад

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!

@anjalisanthosh8307 5 лет назад

I was really worried of question related to LiAlH4 and NaBH4 ...but now its super easy😊😘

@JaiHanuman6636 4 года назад

ru-vid.com/video/%D0%B2%D0%B8%D0%B4%D0%B5%D0%BE-FSdcvzqSD1I.html Reduction of organic compounds

@gino3006 6 месяцев назад

I have my exam on ketone/aldehyde reactions, organometallics, and nitriles tomorrow. Bless you sir

@gino3006 6 месяцев назад

AND imine and enamine formation/hydrolysis😭gotta make sure you have a video for that real quick

@blessingomoyemen1759 3 года назад

I can't believe that 17mins into this video and I already understood reduction mechanism.....you are the man

@kailynwalsh1148 4 года назад

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 :)

@anastasiac680 6 лет назад

Organic chemistry is easy.... when it is explained the way you do 💆🏼💁🏼🤓

@n08ody48 4 года назад

2:50 reduction of ketone(cyclohexanol) using nabh4 5:30 reduction of acyl chloride using nabh4

@adaptercrash Год назад

What is reduced when a mountain is made in emergent reality?

@TreyLee51 11 месяцев назад

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!

@JeffarryLounder Год назад

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?

@Wunderbred66 4 года назад

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.

@ashank728 2 года назад

The clarity in explanation of mechanisms is the best one can get .

@peachy19968 3 месяца назад

Amazing. You explain things so concisely and without the bloat that my class has. Thank you.

@itzcassiieex 7 лет назад

You are the freakin' MAN.

@mrpabloskyoskosky 4 года назад

Man your videos are really really good, even better than the explanation that some teachers give. Thank you!

@lutfanharoon662 7 лет назад

very nice and comprehensive lectures of organic chemistry

@Halo-lg7rq Год назад

You make this so simple, I wish I had your videos for all my classes😭

@julianbeyblade3858 Год назад

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？

@taiahking1226 7 месяцев назад

Watching this during my first mental breakdown of the semester because teachers don't like to test over things they actually teach us 👍

@vlr003 4 года назад

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..

@v.g.vasavidutt1421 6 лет назад

thank you... great explanation!!! you make the concepts of organic chemistry easy to me

@Junior-hq3hy 4 года назад

Absolute legend (God bless you🙏🏾)

@shashikantkumar5095 6 лет назад

This is your first video that I am watching and you are just great!!!👌

@mangaluver1231 3 года назад

You are doing the lord's work. I think I can actually pass o chem 2 thanks to your videos.

@danielmunozmunoz8404 Год назад

you are literally my hero right now, THANK YOU SO MUCH!!!

@zahrah0722 8 дней назад

We love you brother.

@princeagyenim2753 6 лет назад

excellent ....brilliant.....you make organic chemistry so simple

@emteemte3985 4 года назад

you are absolute compltet teacher of the world pure chemist long life thank you very much dear!!!

@massielcastillo363 4 года назад

Oh my gosh why didn't I find you sooner. Bless you and your work! Thank you

@golamsabbirsarker5965 5 лет назад

you are the boss and savior.

@PC-ky3qo 7 лет назад

The explanation was perfect. Thank you very much.👌

@sandeepsinghbisht3489 2 года назад

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?

@ScilexGuitar 5 лет назад

The video I needed before exam!

@tiasa_s_rhythm 3 года назад

This was so helpful, I can't even explain! Thanks for helping me in my second sem of msc. 😇

@christopheromoya535 Год назад

Putting millions of future scienctists in you hand only.....you work is a gem and voters to politicians.🥰

@NuguNgas 6 месяцев назад

You always save my ass before every exams.....may God bless you abundantly

@brianng4933 3 года назад

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.

@iitjee4465 7 лет назад

Excellent videos. Keep it coming.

@rizzmechanics Год назад

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

@minusstage3 2 года назад

Amazing work my friend! Much appreciated!!

@princeklutse4950 4 года назад

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

@shanemichael9404 5 лет назад

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 !

@nope.itsjustmoi3169 2 года назад

You're. The. BEST!

@iltafhussain8352 2 года назад

Think you so much sir the methods is easy and the knowledge is more

@festusruhogoza3689 7 лет назад

Thanks for you're well and indeed explanation

@AP-qd1le 9 месяцев назад

so useful and well explained !! i have a question : is NaBH4 strong enough to an ester to an aldehyde ? thank you !

@chandrashekharkrishnan6141 4 года назад

Thanks paAl! Great explanations

@Jeeprep-dm3pq Год назад

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.

@100zuhaibriyaz5 4 года назад

35:00 Can't we use Diborane to reduce only the ketone group and not the water group?

@sciencescience9102 5 лет назад

Amazing as always!!!! Thank you so much!!!

@darianik6854 Год назад

i love you so much

@guertharomage8075 5 лет назад

Thanks so much for this But lol Him: lithium tert-butoxy Subtitles: lithium to boot oxy

@alish5417 Месяц назад

Why the boron ion is needed for lihb4 to exist ? Why not chlorine ? Lithium chlorohydride for example ؟

@omarqasem3807 5 лет назад

God bless your soul

@1.0gangwarshivam 4 года назад

Lol f***

@sandeep7973 4 года назад

So is dibal h actually tert butyl aluminium hydride?

@PhillipGrayIII 8 месяцев назад

Great explanation. I wish in America we were exposed to this in highschool...

@jesusmrosario-claudio4104 3 года назад

Thank you once again.

@ilanbens1 3 года назад

hey does someone know what is the mechanism for carboxylic acid with LiAlH4?

@anounymous7988 2 года назад

You are amaizing ❤️ Can you pls put and explain all organic reactions for university students chemists 🥺

@nachiketapradhan171 7 лет назад

awesome explanation👌👌👌👍👍👍👍✌️

@quantised1703 6 лет назад

Initially you said we can't reduce aldehydes with LiAlH4 but at 23:00 you are doing the exact same thing!

@chinusaxena963 6 лет назад

quantised he didn’t say That

@nikhilsrivastav1537 6 лет назад

i want some more detail about protection group as... how to protect alcohol and several other functional groups...

@rajeevdangwal4365 4 года назад

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

@iltafhussain8352 2 года назад

Reducing hydrogen means , to reduce the other by giving the electron so it become oxidized itself and reduce the other

@ashleshaupadhyay5864 Год назад

Thank you thank you so much❤

@yasmineeyam9012 6 лет назад

think you so much your videos are excelents

@dianehinvi5674 3 года назад

Really thank you very much .you save us

@Gaish 5 лет назад

you're a god

@afaq289 7 лет назад

Thank you so much for these videos!

@princeklutse4950 4 года назад

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 😟

@MrDSimba 4 года назад

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).

@omarmikha1677 4 года назад

@@MrDSimba so do we use his mechanism or this one? lol

@florianm9693 4 года назад

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

@meriemhouche1840 7 лет назад

great explanation thank you

@jamesh5198 4 года назад

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????

@eniamrahc73 6 лет назад

I'm binging your videos rn

@alish5417 Месяц назад

Lithium aluminum is more reactive why ? Because al has +3 charge ?

@saysHotdogs 11 месяцев назад

How does this man know so much about everything

@IRSArsonist Год назад

anybody get what water does in the DIBALH mechanism?

@loadedupempire7389 5 лет назад

This is amazing,thanks for sharing

@sarahransomm 7 лет назад

thank you so much!!!!

@71_fathurrahman77 4 года назад

Thank you so much

@hazirhy4275 3 года назад

May live long

@Emilie-jg8nw 24 дня назад

hello from france, first thank you so much for that video! you just gained a new subscriber ;) it helped me a lot. And i have just written down everything in a revision sheet. Just a question because i have that case for an exercice: what about LiBH4 for an amide? i know that the alcalin metal can change the reactivity in some cases and i wonder if it would behave as LiAlH4 in that case and just remove the carbonyle? or will it cleave the amide bond and leave an aldehyde first then an alcohol (to me thats the right option)? thank you so much in advance for the answer and sorry if thats a stupid question haha. -Emilie

@teresatran3240 4 года назад

My finals savior

@akashrana4617 6 лет назад

Use of alcoholic solvent not shown????? Is it ryt machanism

@riveratrackrunner 6 лет назад

alchohlic? damn ur to drunk

@lauren042986 3 года назад

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.

@kavyanegi4118 6 лет назад

Electronegativity of hydrogen is 2.2 and that of bromine is 2.96. Last time I checked the math, 2.2 was smaller than 2.96!!

@markokolundzic3748 6 лет назад

Kavya Negi Boron is in the reduction agent not bromine and boron has an electronegativity of 2.0

@truthspeaker9190 5 лет назад

Boron (B) does not equal to Bromine (Br). If you do not use the correct substances, you will not get the correct product. Boron electronegativity is and always was 2.04 It does not change from time to time.

@truthspeaker9190 5 лет назад

And in case your wondering, yes hydrogen is more electronegative that Boron. Some people think that since hydrogen is atomic number 1, it is least electronegative, but its not. Francium actually is in fact the least electronegative.

@mokshithmalugula6122 2 года назад

Why hydrogens in alh3- are nucleophilic and hydrogens in alh3 are not nucleophilic can anyone explain the reason

@gedooka 10 месяцев назад

the goat strikes again

@songohan393 2 года назад

My man carries millions of people for free

@sougatalegend6601 3 года назад

You are best

@parameshbandhubanerjee8697 2 года назад

9:16

@balakrisahnanbk3297 6 лет назад

in 5:09 you didn't show the coordinate bond in hydronium ion

@smarts5057 5 лет назад

is it possible that there is a reduction of alkane?

@bhaswardutta4890 5 лет назад

NO!! There is no room to accommodate any more Hydrogen!!

@raynier250599 4 года назад

I guess u can have ions but that's it

@anilhugoabdulhaqwilliams4613 6 лет назад

How can both the amide and AlH4- lose H+? @25:10?

@RishuKumar-fx1ci 5 лет назад

AlH4 loses H-

@freedomeminexnkubrah3291 4 года назад

thank u

@tomasblovsky5871 7 лет назад

Ethylene glycol will turn the ketone into a what, please?

@jatinyadav1930 7 лет назад

Hakeshi Wakuro it will convert alcohol into cyclic kital

@nogagamal935 6 лет назад

Cohol

@farazahmadriaz3352 5 лет назад

sir ur audio quality is very low ,it is very diffcult to hear ,plzzz sir upgrade it

@kristinwade344 5 лет назад

so I rewatched the first min a few times... you said.. you would draw ketone aldehyde carboxylic acid to react with nabh4.. right.. but then say it cant react with carboxylic acids and esters.. but you do the reaction.. this is very confusing..the 3 structure is an acyl chloride..just looked it up.. so these are reactive and not carbo acids

@ateata7854 5 лет назад

To make carboxylic acid more reactive you use something like SOCl2 to substitute the OH with a Cl, then you can make it react with hydride since Cl- is a good leaving group, better than OH-