Thank you so so much The Organic Chemistry Tutor! I watched all of the videos which helped me gain a clear and stronger foundation for Organic Chemistry 2, which helped me pass Organic Chemistry 2! I couldn’t be more grateful to have found and come across your TH-cam Channel, you helped not just me but so manyyy! Thank you for all that you do!🙏🙏
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.
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
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 :)
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
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??
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?
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.
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 🤦
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.
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.
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.
![[LIVE] : ONE ลุมพินี 88 | คู่เอก "ป้อมเพชร vs อัสลามจอน"](http://i.ytimg.com/vi/1ZqTVVbMgbo/mqdefault.jpg)
Final Exams and Video Playlists: www.video-tutor.net/
You have literally saved me from failing an organic chemistry test. Thank the lord I saw this video, I was completely lost before
this guy is really helpful i always watch his videos when i need a help
Thank you so so much The Organic Chemistry Tutor! I watched all of the videos which helped me gain a clear and stronger foundation for Organic Chemistry 2, which helped me pass Organic Chemistry 2! I couldn’t be more grateful to have found and come across your TH-cam Channel, you helped not just me but so manyyy! Thank you for all that you do!🙏🙏
It's really helpful to me and almost all doubts clearing lecture regarding organic chemistry 👍👍👍👍👍🎉🎉I found it very helpful . Thanku very much 🙏
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.
You're right. NaBH4 can't reduce an ester. I just made the corrections.
see my answer on Alexandra Long's question
I wanna like this video a 1000 times!
Put it simply u don't wanna like the video. 1 click -liked ,next click remove like ,so on ,performing this 1000 times
Amazing video. Thanks for spending time on each equation!
This is what i was looking for, thanks for this.
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
U r grt man.... appreciation to this guy... from India 👍
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 :)
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
got a test Monday, wish me luck!
how'd it go?
Nermina Kovacevic I passed with a 90 :)
Still helping so much in 2021 ty
Beautiful video
Ur videos are so good thank you
thank you sir for this video making because i am very need
Thank you once again.
Thanks a lot for this
انا بحبك يا اخي بحبك
27:17 double bond missing top right
Thank you so much
thank you so much sir but how can I care about your video?! I want all of them.please.
❤
thank you!!!
I love you
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??
23:57 isn't there an additional carbon here ?,in the chain attached to benzene
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?
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.
R- is the conjugate of alkane so it is a very very strong base hence a super strong nucleophile
where did the h3o came from
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 🤦
that would be very time-taking , also the zig zag is the modern version of drawing the chains.
I thought NaBH4 doesn't reduce esters? It's not strong enough.
Yes that's right. Where did I make the mistake?
@@TheOrganicChemistryTutor hi there, at around 16:54
see my answer on Alexandra Long's question
why does addition of nucleophile and addition of acid are not added at the same time? Please answerrr
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.
can enamine be reduced by NaBH4?
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.
1year gone am so sorry kid, we cant all win.🙁
@@WahPedal-h6x honestly I forgot about this 😆
2:33 why the methyl group attack and not the bromide atom?
Peta-Gay Smith yeah,i doubt that too
Bromide ion has noble gas configuration ,so it will not give electron
I think this maybe the reason
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
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.
Country
00:16:50
Thanks. I just made the corrections.
No problem. Thank-you for these amazing videos. I hope you'll keep them coming.
You're welcome. I just have to watch out for future mistakes.
see my answer on Alexandra Long's question