Slight correction at 9:56 aniline doesn’t show friedel crafts rxn as nh2 ends up donating it lone-pair to febr3 hence br+ isn’t formed in grt amount becoz of the impurity...hence this method is also not suitable.
Ritu Agrawal..............Are you sure? Because i thought when doing an electrophillic aromatic halogenation (adding a halogen to a benzene ring) if the ring contains a strongly activating substituent such as -OH, -OR or AMINES, a catalyst is not necessary for SIMPLE(single) halogenation. BUT BUT if you used a catalyst AND EXCESS halogen then you get the tri halogen benzene. Are you saying this is NOT true??????
@@johnblacksuperchemist2556 All im saying is aniline(only) doesn't show Friedel crafts reaction... because it has a tendency to donate its lp of e to febr3.This may happen everytime when a group that is a better nucleophile in comparison to bromine is attached to benzene ring.
@@rituagrawal7325 ............Sorry buddy i thought you were calling the halogenation reaction in the video a friedel crafts reaction because they are so SIMILAR. I understand what you are saying now and thank you. I will put that in my notes about the aniline and FeBr3. That is something i did not know. I wander if you can isolate the aniline FeBr3 coordination complex and do some experiments with it............................ Just my OPINION and i am totally guessing but i think triple halogenation of aniline works with an excess of halogen and that would be the MAIN product. But some of the FeBr3 would react with the lone pair on the NH2 and that would be a very MINOR product. Just talking out my ass though really
For 10:13 , why not add HNO3 H2So4 again two more times since NO2 is a meta director? Is it because it is a deactivator meaning that it would be slower and harder to add?
I have a question about 9:25. Can i put Br2/FeBr3 before reducing the NO2 group and than use sandmeyer reaction to change the NO2 group into the last Br?
Giovanni..................No you can not. NO2 is a STRONGLY DEACTIVATING group. So it is a meta director. So I am guessing it would add 2 bromine in the meta position and stop. At that point i would guess that no more bromine(halogen) would add. And I would guess you would be left with 3_5_ di bromo_1_nitrobenzene as your main product......................OR since BOTH bromine and NO2 are both DEACTIVATING groups you MIGHT only get one bromine add to the nitrobenzene making 3_bromo_1_nitrobenzene OR the second bromide might add para or ortho compared to the first bromine placed on the ring. Not really sure but i do know you will not get a triple addition of the bromine if you have NO2 instead of NH2 on the ring at the get go
That's a good question though. It is impossible because while nitro is meta directing, only monosubstituion will occur - and that's at best. Nitro is one of the most deactivating groups there is.
Hi! I have a question about 7:35 of this video. Why is the bromine ortho and para director (activating group) the first time, and then a meta director (deactivating group) the second time? And thank you so much for your great videos:)
Katie Brown ...........If by N2+ you mean the diazonium compound then it would be considered a meta director. That being said..........I do not think you would make a diazonium compound so you could add more stuff to the ring. You make the diazonium compound so you can react that diazonium functional group ........meaning to change the diazonium group(N2+) into another group. Or to do a coupling reaction. The benzene ring gets its reactivity from it's electron density. It is not negative but with all the double bonds/pi bond there is a lot of electron density above and below the ring. So if the ring gets its power or reactivity from have a high electron density then anything that GIVES/donates it electrons to benzene makes it MORE reactive. It ACTIVATES the ring. So if something is attached to the ring that is + .............like N2+.......that would suck electron density AWAY from the ring and there for make the ring less reactive. And that deactivates the ring. Things that deactivate the ring are meta directors. And N2+ is + so it will suck electrons away from the ring and deactivate it. There for it would be a meta director. Keep in mind the halogens like chlorine are SPECIAL. Functional groups that have lone pair electrons USUALLY can donate to the ring and active it making the functional group an ortho para director. Like OH groups or OR groups. But chlorine is SO ELECTRONEGATIVE that even thought it has a lot of lone pair electrons it still DEACTIVATES the ring cause it is SOOOOOOOO electronegative it sucks all the electron density AWAY from the ring. And the ring gets it power/reactivity from its electron density. BUT BUT BUT because it does have lone pair electrons it is an ortho para director instead of a meta director like MOST deactivating functional groups. Because like you said........lone pair electrons can add to the resonance of the ring. And the resonance structures with a halogen on a ring will always place the negative charge on the ortho and para positions................HOPE THIS HELPED
Fluorination is incorrect. If you just use HBF4 on a diazonium salt, it simply exchanges the Cl- ion from the HCl in the diazotization for BF4-. You will need to use heat to facilitate the fluorination.
would addition of NaOH after the formation of the N2 group not also replace it with an -OH group? Im thinking specifically in the case of phenethylamine being the substrate for the reaction.
I need a little help with a reaction I'm trying for the production of Sulfasalazine. I've got sulfapyridine with HCl and Sodium Nitrite which is hopefully giving the azo salt where the amino group is on the sulfapyridine. Then I've got salicylic acid and NaOH to protonated the phenol of the salicylic acid to delocalise the electron and have binding between the triple nitrogen and the meta position of the salicylic acid. I don't believe the reaction is going as planned but can't seem to see where things go wrong. Melting point of the product doesn't match my reference sample of Sulfasalazine and doesn't match IR spectroscopy either. Chemistry isn't my strong suit but I can't figure it out. Have you got an opinion on what ight be happening?
I came here to understand Sand Meyer reaction and I ended up playing with compounds......great video I actually enjoyed it
Great videos as always. Thanks to you I'm first in my class. Keep up the great work my man.
I sincerely appreciate the effort you put into delivering valuable content.
Love your way of teaching MASSIVE respect to you sir.
Thank you so much for helping in my exams.
Slight correction at 9:56 aniline doesn’t show friedel crafts rxn as nh2 ends up donating it lone-pair to febr3 hence br+ isn’t formed in grt amount becoz of the impurity...hence this method is also not suitable.
Ritu Agrawal..............Are you sure? Because i thought when doing an electrophillic aromatic halogenation (adding a halogen to a benzene ring) if the ring contains a strongly activating substituent such as -OH, -OR or AMINES, a catalyst is not necessary for SIMPLE(single) halogenation. BUT BUT if you used a catalyst AND EXCESS halogen then you get the tri halogen benzene. Are you saying this is NOT true??????
@@johnblacksuperchemist2556 All im saying is aniline(only) doesn't show Friedel crafts reaction... because it has a tendency to donate its lp of e to febr3.This may happen everytime when a group that is a better nucleophile in comparison to bromine is attached to benzene ring.
@@rituagrawal7325 ............Sorry buddy i thought you were calling the halogenation reaction in the video a friedel crafts reaction because they are so SIMILAR. I understand what you are saying now and thank you. I will put that in my notes about the aniline and FeBr3. That is something i did not know. I wander if you can isolate the aniline FeBr3 coordination complex and do some experiments with it............................
Just my OPINION and i am totally guessing but i think triple halogenation of aniline works with an excess of halogen and that would be the MAIN product. But some of the FeBr3 would react with the lone pair on the NH2 and that would be a very MINOR product. Just talking out my ass though really
GREAT VIDEO AS USUAL
Nice I can understand thank you
Personally I prefer the Oscarmayer reaction that adds a hotdog to the benzene ring. But in all seriousness, thanks for another amazing video!
Good presentation thanks
For 10:13 , why not add HNO3 H2So4 again two more times since NO2 is a meta director? Is it because it is a deactivator meaning that it would be slower and harder to add?
I thought this too! but i think it might be because trinitro benzene is explosive (sorry this is 2 years late lol)
I have a question about 9:25. Can i put Br2/FeBr3 before reducing the NO2 group and than use sandmeyer reaction to change the NO2 group into the last Br?
Giovanni..................No you can not. NO2 is a STRONGLY DEACTIVATING group. So it is a meta director. So I am guessing it would add 2 bromine in the meta position and stop. At that point i would guess that no more bromine(halogen) would add. And I would guess you would be left with 3_5_ di bromo_1_nitrobenzene as your main product......................OR since BOTH bromine and NO2 are both DEACTIVATING groups you MIGHT only get one bromine add to the nitrobenzene making 3_bromo_1_nitrobenzene OR the second bromide might add para or ortho compared to the first bromine placed on the ring. Not really sure but i do know you will not get a triple addition of the bromine if you have NO2 instead of NH2 on the ring at the get go
That's a good question though. It is impossible because while nitro is meta directing, only monosubstituion will occur - and that's at best. Nitro is one of the most deactivating groups there is.
Can this reaction be performed if the molecule has an Ester?
Hi! I have a question about 7:35 of this video. Why is the bromine ortho and para director (activating group) the first time, and then a meta director (deactivating group) the second time? And thank you so much for your great videos:)
심지나 good question!
Bromide directs in ortho para position to its own location (it just happens to be the meta position of the amine)
Thank you so much.
is N2+ a meta director? since it doesn't have lone pairs to add to resonance?
Katie Brown ...........If by N2+ you mean the diazonium compound then it would be considered a meta director. That being said..........I do not think you would make a diazonium compound so you could add more stuff to the ring. You make the diazonium compound so you can react that diazonium functional group ........meaning to change the diazonium group(N2+) into another group. Or to do a coupling reaction.
The benzene ring gets its reactivity from it's electron density. It is not negative but with all the double bonds/pi bond there is a lot of electron density above and below the ring. So if the ring gets its power or reactivity from have a high electron density then anything that GIVES/donates it electrons to benzene makes it MORE reactive. It ACTIVATES the ring. So if something is attached to the ring that is + .............like N2+.......that would suck electron density AWAY from the ring and there for make the ring less reactive. And that deactivates the ring. Things that deactivate the ring are meta directors. And N2+ is + so it will suck electrons away from the ring and deactivate it. There for it would be a meta director.
Keep in mind the halogens like chlorine are SPECIAL. Functional groups that have lone pair electrons USUALLY can donate to the ring and active it making the functional group an ortho para director. Like OH groups or OR groups. But chlorine is SO ELECTRONEGATIVE that even thought it has a lot of lone pair electrons it still DEACTIVATES the ring cause it is SOOOOOOOO electronegative it sucks all the electron density AWAY from the ring. And the ring gets it power/reactivity from its electron density. BUT BUT BUT because it does have lone pair electrons it is an ortho para director instead of a meta director like MOST deactivating functional groups. Because like you said........lone pair electrons can add to the resonance of the ring. And the resonance structures with a halogen on a ring will always place the negative charge on the ortho and para positions................HOPE THIS HELPED
is the mechanism for phenol same as that for 2-Naphthol
What is the difference between additional elimination and elimination additional as you had represented it in Nucleophilic reaction
Fluorination is incorrect. If you just use HBF4 on a diazonium salt, it simply exchanges the Cl- ion from the HCl in the diazotization for BF4-. You will need to use heat to facilitate the fluorination.
hello is it possible to convert NO2 into NH2 with Fe, HCl instead of Zn
Super!
would addition of NaOH after the formation of the N2 group not also replace it with an -OH group? Im thinking specifically in the case of phenethylamine being the substrate for the reaction.
I need a little help with a reaction I'm trying for the production of Sulfasalazine. I've got sulfapyridine with HCl and Sodium Nitrite which is hopefully giving the azo salt where the amino group is on the sulfapyridine.
Then I've got salicylic acid and NaOH to protonated the phenol of the salicylic acid to delocalise the electron and have binding between the triple nitrogen and the meta position of the salicylic acid.
I don't believe the reaction is going as planned but can't seem to see where things go wrong. Melting point of the product doesn't match my reference sample of Sulfasalazine and doesn't match IR spectroscopy either. Chemistry isn't my strong suit but I can't figure it out.
Have you got an opinion on what ight be happening?
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Seriously how are you able to publish all of these videos? Are your recording constantly to make more money?