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Topic: organic chemistry 2  (Read 5637 times)

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Offline Raghuveer

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organic chemistry 2
« on: May 15, 2012, 02:50:57 AM »
Is it possible to synthesize 4-acetyl phthalimide. or why is acetylation of phthalimide on 4th position  practically not possible??? suggest an alternative method for the synthesis of 4-acetyl phthalimide??
« Last Edit: May 15, 2012, 03:09:01 AM by Dan »

Offline Raghuveer

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organic chemistry 1
« Reply #1 on: May 15, 2012, 02:53:36 AM »
is it possible to practically synthesize 3-bromo,5-nitroacetophenone
« Last Edit: May 15, 2012, 03:08:49 AM by Dan »

Offline 408

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Re: organic chemistry 1
« Reply #2 on: May 15, 2012, 04:20:43 AM »
yes, yes it is.

Offline DrCMS

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Re: organic chemistry 1
« Reply #3 on: May 15, 2012, 05:09:26 AM »
yes, yes it is.

Good answer  ;), bad question :(

Offline Arkcon

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Re: organic chemistry 2
« Reply #4 on: May 15, 2012, 09:18:30 AM »
Raghuveer:, I hope you don't mind my merging your two topics.  They're both the same, in that they both contain very limited information from you.  Try to show us more about what you know, what you've tried, and what you've learned, so we can give useful help.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline orgopete

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Re: organic chemistry 2
« Reply #5 on: May 15, 2012, 06:05:49 PM »
Can't you synthesize it from 1,2,4-benzenetricarboxylic acid anhydride?
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Raghuveer

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Re: organic chemistry 2
« Reply #6 on: May 18, 2012, 04:40:41 AM »
Raghuveer:, I hope you don't mind my merging your two topics.  They're both the same, in that they both contain very limited information from you.  Try to show us more about what you know, what you've tried, and what you've learned, so we can give useful help.
i want to synthesize 4-acetyl phthalimide from phthalimide. I have tried all the available acetylation procedures but failed----- 
Rxn condition i)CH3COCl / AlCl3/ anhydrous conditions/controlled reflux 
Rxn condition  ii)Acetic anhydride/AlCl3/anhydrous conditions/controlled reflux
Rxn condition iii) CH3COCl / AlCl3/ anhydrous conditions/ice cold stiring
Rxn condition iv) Acetic anhydride/ AlCl3/ anhydrous conditions/ice cold stiring
Rxn condition v)CH3COCl / Zn/ anhydrous conditions/controlled reflux 
Rxn condition vi)CH3COCl / Zn/ anhydrous conditions/ice cold stiring
Rxn condition  vii)Acetic anhydride/Zn/anhydrous conditions/controlled reflux
Rxn condition  ii)Acetic anhydride/Zn/anhydrous conditions/ice cold stiring
 and i have also subjected the same for microwave heating


Offline Raghuveer

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Re: organic chemistry 2
« Reply #7 on: May 18, 2012, 04:42:07 AM »
can you suggest me the procedure

Offline Raghuveer

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Re: organic chemistry 1
« Reply #8 on: May 18, 2012, 04:44:59 AM »
yes, yes it is.

Good answer  ;), bad question :(
There is nothing good or bad buddy.. first go through my question thoroughly.. put it on paper and then answer it.. i have been trying both the schemes from 3 months, but i couldnt get the results...

Offline sjb

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Re: organic chemistry 2
« Reply #9 on: May 18, 2012, 06:08:03 AM »
Raghuveer:, I hope you don't mind my merging your two topics.  They're both the same, in that they both contain very limited information from you.  Try to show us more about what you know, what you've tried, and what you've learned, so we can give useful help.
i want to synthesize 4-acetyl phthalimide from phthalimide. I have tried all the available acetylation procedures but failed----- 
Rxn condition i)CH3COCl / AlCl3/ anhydrous conditions/controlled reflux 
Rxn condition  ii)Acetic anhydride/AlCl3/anhydrous conditions/controlled reflux
Rxn condition iii) CH3COCl / AlCl3/ anhydrous conditions/ice cold stiring
Rxn condition iv) Acetic anhydride/ AlCl3/ anhydrous conditions/ice cold stiring
Rxn condition v)CH3COCl / Zn/ anhydrous conditions/controlled reflux 
Rxn condition vi)CH3COCl / Zn/ anhydrous conditions/ice cold stiring
Rxn condition  vii)Acetic anhydride/Zn/anhydrous conditions/controlled reflux
Rxn condition  ii)Acetic anhydride/Zn/anhydrous conditions/ice cold stiring
 and i have also subjected the same for microwave heating

Do you get any product out of these? Seems you may get some N-acylation as the imide proton is very acidic. Could you form something like 4-acetyl-1,2-benzenedicarboxylic acid and ring close that?

Offline orgopete

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Re: organic chemistry 2
« Reply #10 on: May 18, 2012, 09:31:03 AM »
It should not be a surprise that acylation failed. Acylium ions are less reactive and a phthalimide is a deactivated benzene ring, see http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/benzrx1.htm#benz7.

I think you will have to introduce an activating group that you can remove after acylation, or introduce functionality that you can transform into an acetyl group.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline DrCMS

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Re: organic chemistry 1
« Reply #11 on: May 18, 2012, 10:40:48 AM »
yes, yes it is.

Good answer  ;), bad question :(
There is nothing good or bad buddy.. first go through my question thoroughly.. put it on paper and then answer it.. i have been trying both the schemes from 3 months, but i couldnt get the results...


I'm not your buddy and is was a stupidly bad question.  You just asked if it was possibly to make 3-bromo,5-nitroacetophenone.  How to do it in sufficient yield and how to isolate the desired material, is the questions you should have asked but did not because you were too damn lazy to be clear from the start what you wanted to do and what you had already tried.

So because you originally posted a very poorly worded very broad question you did not initially get any helpful replies, that is your fault not ours.

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