Is this reaction mechanism correct?
Original post by asaaal
Your very first step; look up in books about mechanism(s) on how amines usually act as nucleophile. The hydrogen on amine is not lost immediately when an amine protonates or attack a carbonyl.
Original post by asaaal
Original post by shengoc
Your very first step; look up in books about mechanism(s) on how amines usually act as nucleophile. The hydrogen on amine is not lost immediately when an amine protonates or attack a carbonyl.
Yes, lone pair attacks giving a positively charged nitrogen species after having lost the acetate anion. You can then use this to deprotonate the positively charged amino nitrogen
Original post by JMaydom
Yes, lone pair attacks giving a positively charged nitrogen species after having lost the acetate anion. You can then use this to deprotonate the positively charged amino nitrogen
ive read your feedbacks several times and i dont understand
would you be able to draw the part you think ive done wrong if its not too much of a pain?
Original post by asaaal
ive read your feedbacks several times and i dont understand would you be able to draw the part you think ive done wrong if its not too much of a pain?
would you be able to draw the part you think ive done wrong if its not too much of a pain?Attack the anhydride with the nitrogen atom to generate a 4 coordinate, positively charged nitrogen intermediate, which then loses a proton.
Original post by asaaal
ive read your feedbacks several times and i dont understand would you be able to draw the part you think ive done wrong if its not too much of a pain?
would you be able to draw the part you think ive done wrong if its not too much of a pain?Original post by illusionz
Attack the anhydride with the nitrogen atom to generate a 4 coordinate, positively charged nitrogen intermediate, which then loses a proton.
Yeah, better worded by Illusionz. See if you understand now... If not i'll draw it out.
Original post by JMaydom
Yeah, better worded by Illusionz. See if you understand now... If not i'll draw it out.
i really dont understand
im so sorry could you draw it out?Original post by asaaal
i really dont understand im so sorry could you draw it out?
im so sorry could you draw it out?Hopefully the picture has successfully attached. Here is the mechanism!
Sorry the picture is a bit blurred but I had to take the photo on my phone.
Original post by JMaydom
Hopefully the picture has successfully attached. Here is the mechanism!
Sorry the picture is a bit blurred but I had to take the photo on my phone.
Sorry the picture is a bit blurred but I had to take the photo on my phone.
I wouldn't use the double headed arrow in this case because the positively charged N is probably a better leaving group than the carboxylate. At least, that was what I was told by one of the academics in a 2nd year practical write up. I've always lost the proton before carbonyl reformation since then. That said, I don't know how important it actually is...
Original post by illusionz
I wouldn't use the double headed arrow in this case because the positively charged N is probably a better leaving group than the carboxylate. At least, that was what I was told by one of the academics in a 2nd year practical write up. I've always lost the proton before carbonyl reformation since then. That said, I don't know how important it actually is...
It's not an issue with our examiners. So long as it is feasible (seeing as the whole thing is one great equilibrium of many intermediates) they are happy. Obviously as the positive N is a better leaving group, mostly it will be kicked back out but that is not the productive pathway so you ca ignore it.
Really I should have put equilibrium arrows!!!
Original post by JMaydom
It's not an issue with our examiners. So long as it is feasible (seeing as the whole thing is one great equilibrium of many intermediates) they are happy. Obviously as the positive N is a better leaving group, mostly it will be kicked back out but that is not the productive pathway so you ca ignore it.
Really I should have put equilibrium arrows!!!
Really I should have put equilibrium arrows!!!
True. I remember thinking he was being a bit pedantic, but it's just something I've always done ever since
Original post by illusionz
I wouldn't use the double headed arrow in this case because the positively charged N is probably a better leaving group than the carboxylate. At least, that was what I was told by one of the academics in a 2nd year practical write up. I've always lost the proton before carbonyl reformation since then. That said, I don't know how important it actually is...
what arrow should be used instead of the double headed one?
Original post by JMaydom
Hopefully the picture has successfully attached. Here is the mechanism!
Sorry the picture is a bit blurred but I had to take the photo on my phone.
Sorry the picture is a bit blurred but I had to take the photo on my phone.
you life saver !! thank you so much !!
Quick Reply
Related discussions
- amines
- SN1 and SN2 reactions (chemistry)
- Mechanics issue
- Edexcel A-Level Chem Paper 2 Advanced Organic and Physical Chemistry [Exam Chat]
- mechanics 1 math
- AQA A Level Mathematics Paper 2 (7357/2) - 13th June 2023 [Exam Chat]
- A Level Chemistry Organic Help
- chemistry a level
- AS Mechanics
- Chemistry help
- Organic chemistry learning a-level
- Could someone please help with a mechansim question.
- outline a mechanism for the reaction of bromomethane with an excess of compound J
- Do you need to know Acylation mechanism for A level OCR chemistry ?
- PLEASE Help ME-CHEMISTRY 😭
- AQA A-Level Chemistry Paper 2 (7405/2) - 19th June 2023 [Exam Chat]
- Chemistry aqa a-level organic
- AQA A Level Chemistry
- ocr a level chemistry mechanisms and pathways
- Tips for drawing components of forces in A-level Maths mechanics
Latest
Last reply 3 minutes ago
JK Rowling in ‘arrest me’ challenge over hate crime lawLast reply 4 minutes ago
Official University of Edinburgh Applicant Thread for 2024Last reply 22 minutes ago
Woodhouse College applicants 2024
