Nucleophilic Addition Reaction Mechanism, Grignard Reagent, NaBH4, LiAlH4, Imine, Enamine, Reduction

This organic chemistry video tutorial focuses the mechanism of nucleophilic addition reaction to aldehydes and ketones. This video contains plenty of examples and practice problems using grignard reagents, NaBH4, LiAlH4, DIBAl, and amines.
Here is a list of topic:
1. Nucleophilic Addition Reaction Mechanism
2. Grignard Reagent Synthesis Reaction Mechanism With Aldehydes and Ketones
3. Grignard Reagent With Esters, CO2, and Ethylene Oxide / Epoxide
4. Reduction of Aldehydes, Ketones, Esters, and Acid Chlorides with NaBH4 and LiAlH4
5. NaBH4 Reaction Mechanism
6. LiAlH4 Reduction Mechanism - Hydride Ion Transfer
7. Cyanohydrin Formation Reaction Mechanism
8. Dibal Reaction - Synthesis of Aldehydes
9. Synthesis of Primary, Secondary, and Tertiary Alcohols
10. Imine Formation Reaction
11. Enamine Formation Reaction Mechanism
12. Primary vs Secondary Amines
13. Reductive Amination - NaBH3CN
14. Reduction of Lactones
15. Conjugate Addition vs Direct Addition - Alpha Beta Unsaturated Ketones

[@TheOrganicChemistryTutor]

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[@twistidbow3594]

hi, sorry if I missed something at 17:00 but my professor said you can't reduce lactone with NaBH4. The lactone is in equilibrium with its branched form which has an alcohol and a carboxylic acid. NaBH4 doesn't reduce acids. You either use LiAlH4, or dibal-H and then NaBH4.

[@TheOrganicChemistryTutor]

You're right. NaBH4 can't reduce an ester. I just made the corrections.

[@lorisdupont2177]

see my answer on Alexandra Long's question

[@anastasiac680]

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[@jigyansudash5403]

Put it simply u don't wanna like the video. 1 click -liked ,next click remove like ,so on ,performing this 1000 times

[@rahulmathias8758]

Amazing video. Thanks for spending time on each equation!

[@lorisdupont2177]

Hi, (long text for better understanding/clarifications)
My source is my uni teacher and his book,"Organic Chemistry, J. CLAYDEN" and I'm going to tell people some inconsistancy/ deepening about the video.
First, as I replied to Alexandra Long, at 17:00, NaBH4 CAN reduce lactones (go check the answer below her comment).
Secondly, you told that the reaction of nucleophilic attack by a secondary amine on a carbonyl carbon was done in more acidic conditions than for the primar amine.
You should have talked about pH affecting the reaction/kinetics here.
This reaction is done at a 4

[@akathir7434]

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[@Sesj02]

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[@alexandralong5365]

At 18:47, there shouldn't be a reaction when an ester reacts with NaBH4. NaBH4 is more selective than LAH, therefore it can only react with Ketone and Aldehyde. With ester and carboxylic there are no reactions when it reacts with NaBH4. However as for LAH, it can react with anything that has C=O bond. I am just making sure haha :)

[@lorisdupont2177]

Hi, lactones aren't classic esters. As said in the Organic Chemistry J. Clayden book : " Some esters - lactones ,for example- cannot lie cis for steric reasons and this is one of the reasons why lactones are distinctly more reactives than esters and in many reactions behave more like ketones: lactones are quite easy to reduce with NaBH4, for example".
So, to understand the cis configuration, you should know that esters (lactones as well) have two mesomeric forms following to the delocalization of the oxygen's lone pair. The C-O bond (in the cycle) has so a double bond trait, and so, there are cis and trans configuration. When you look at the structure of a lactone, you can see that, because of the cycle, we only see the trans configuration (oxygen is the main substituant) that is not stabilized (it is linked to orbitals overlap, hard to describe here). As lactones are not stabilized by cis configuration, they are more reactives than classic esters and so can be reduced by softer reducing agent (NaBH4).
My professor (chemistry uni) uses the book I mentionned earlier to teach students as me, I'm so conviced that it is true. Sorry for being late :p

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[@anirudhtammireddy464]

27:17 double bond missing top right

[@flip.3563]

Beautiful video

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[@jesusmrosario-claudio4104]

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[@RenegadeFury]

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[@sarveshambavade]

23:57 isn't there an additional carbon here ?,in the chain attached to benzene

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[@christophemakilanko4704]

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[@Joe-ml4qu]

At 3:09, if the bromine ion also has a negative charge why does it not bond to the carbon instead of the CH3? Is there a preference law/condition here?

[@tylerschrand1834]

both are negativley charged. It woldnt be favored energetically bc there's 2 extra electrons. its like C:Mg2+:Br if that makes sense. since Mg is 2+, its stabilizing both ions.

[@septromnation7840]

R- is the conjugate of alkane so it is a very very strong base hence a super strong nucleophile

[@bobu5213]

My book has a question saying: Give the mechanism for the synthetic conversion of Ph-CHO to Ph-CO-Ph. But this seems like an aldehyde could never become a ketone by nucleophilic addition. What am I missing I am so lost??

[@yashikaraghuwanshi7634]

I thought NaBH4 doesn't reduce esters? It's not strong enough.

[@TheOrganicChemistryTutor]

Yes that's right. Where did I make the mistake?

[@sakeenahjaffer4027]

@@TheOrganicChemistryTutor hi there, at around 16:54

[@lorisdupont2177]

see my answer on Alexandra Long's question

[@iangabrielvictorio7196]

where did the h3o came from

[@nasramohamed2017]

Thanks a lot The Organic Tutor..Can you also use the normal symbols of carbon and hydrogen in those chains than the zigzag pattern please? It's kinda confusing 🤦

[@ummchilesoanyways1313]

that would be very time-taking , also the zig zag is the modern version of drawing the chains.

[@Daniela-rt6el]

why does addition of nucleophile and addition of acid are not added at the same time? Please answerrr

[@jhansi61]

If the acid is water, then in cases like organometallics reagents or LiAlH4,adding both water and the reagent at the same time will be problematic as water destroys the organometallic compound or with LiAlH4 giving a fast exothermic reaction. Any protic acid will behave similarly. So it is made sure that water or protic acid must not be present during the addition of any organometallic reagent or LiAlH4.So it is added at the end of the reaction. It is called work up.

[@rawanwalid15]

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[@XxMyPandoraBoxXx]

can enamine be reduced by NaBH4?

[@arishbamemon8929]

For the first example why would CH3 have a negative charge when it's neutral and why would it be broken off to join cyclopentanol and not Br. Can someone explain please, it's confusing.

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[@panchetawest30]

2:33 why the methyl group attack and not the bromide atom?

[@emptyblank9943]

Peta-Gay Smith yeah,i doubt that too

[@ShubhamSharma-be5bw]

Bromide ion has noble gas configuration ,so it will not give electron
I think this maybe the reason

[@nicholascooper2438]

Right… A bromide ion can hold a negative charge much better than a carbide ion due to it's size, making the carbide ion a much better nucleophile

[@amosepelman3472]

Because that is not how a grignard reaction works. If you continue watching he explains how the methyl group has nucelophillic properties. The bromine does not attack because since bromine is a good leaving group. If it attacked it would just be replaced by the CH3 which does not hold negative charge well whereas the Bromine can hold negative charge well.

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[@uathrhsalim]

7:14

[@yashikaraghuwanshi7634]

00:16:50

[@TheOrganicChemistryTutor]

Thanks. I just made the corrections.

[@yashikaraghuwanshi7634]

No problem. Thank-you for these amazing videos. I hope you'll keep them coming.

[@TheOrganicChemistryTutor]

You're welcome. I just have to watch out for future mistakes.

[@lorisdupont2177]

see my answer on Alexandra Long's question