Shinjimonkey
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How do you speed up the halogenation of benzene (benzene + ICl) at room temperature? I need two points, could someone help me with this?

Thank you very much.
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username1539513
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(Original post by Shinjimonkey)
How do you speed up the halogenation of benzene (benzene + ICl) at room temperature? I need two points, could someone help me with this?

Thank you very much.
alow


Your time to shine?

I would have thought adding a catalyst would speed it up, same with increasing the volumes of the reagants or conversely increasing the pressure?
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alow
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ICl is a solid or liquid near room temp, so increase the concentration of that if you're working in a solvent. Also you could use a Lewis acid catalyst, one that binds well with Cl, to speed up the iodination of benzene.
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username1539513
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(Original post by alow)
ICl is a solid or liquid near room temp, so increase the concentration of that if you're working in a solvent. Also you could use a Lewis acid catalyst, one that binds well with Cl, to speed up the iodination of benzene.
Basically everything you say haha

OP, would you like to join the A-level chemistry whatsapp group we have?

Shinjimonkey
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Shinjimonkey
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(Original post by alow)
ICl is a solid or liquid near room temp, so increase the concentration of that if you're working in a solvent. Also you could use a Lewis acid catalyst, one that binds well with Cl, to speed up the iodination of benzene.
What kind of catalyst/acid can we use to speed the process? I know if you when you want to react benzene and Br2 you can use FeBr2 as a halogen-carrier catalyst, but what can mix when you are trying to do the halogenation of benzene with ICl?
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alow
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(Original post by Shinjimonkey)
What kind of catalyst/acid can we use to speed the process? I know if you when you want to react benzene and Br2 you can use FeBr2 as a halogen-carrier catalyst, but what can mix when you are trying to do the halogenation of benzene with ICl?
AlCl3 should work well.
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Shinjimonkey
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(Original post by alow)
AlCl3 should work well.
If I was to use AlCl3, how would I get the electrophile? To get the electrophile I+ am I right in saying:
AlCl3 + ICl -> I+ + AlCL4-
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alow
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(Original post by Shinjimonkey)
If I was to use AlCl3, how would I get the electrophile? To get the electrophile I+ am I right in saying:
AlCl3 + ICl -> I+ + AlCL4-
Yes that's right.
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Shinjimonkey
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(Original post by alow)
Yes that's right.
Fantastic, thank you very much! If it is ok with you, I would like to ask another thing. I need to turn benzene into iodobenzene by adding I2. It is a similar process but how do you form a good I+ electrophile? is it:
I2 + HNO3 -> I+ + HNO3I-?
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(Original post by Shinjimonkey)
Fantastic, thank you very much! If it is ok with you, I would like to ask another thing. I need to turn benzene into iodobenzene by adding I2. It is a similar process but how do you form a good I+ electrophile? is it:
I2 + HNO3 -> I+ + HNO3I-?
It's this:

2H+ + 2HNO3 + I2 ---> 2I+ + 2NO2 + 2H2O
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Shinjimonkey
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(Original post by alow)
It's this:

2H+ + 2HNO3 + I2 ---> 2I+ + 2NO2 + 2H2O
Where do you get the H+ from?
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alow
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(Original post by Shinjimonkey)
Where do you get the H+ from?
Some of the nitric acid molecules will be dissociated, some will not. It's effectively a proton from nitric acid.
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(Original post by alow)
Some of the nitric acid molecules will be dissociated, some will not. It's effectively a proton from nitric acid.
I see. You are very helpful. Can I ask another question? Promise this will be last. How would you turn iodobenzene into iodo cyclohexane?
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(Original post by Shinjimonkey)
I see. You are very helpful. Can I ask another question? Promise this will be last. How would you turn iodobenzene into iodo cyclohexane?
I would think you could just use really really high pressure and temperatures hydrogen and a Ni catalyst. I'm not massively sure about that though.
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