acyl chloride and benzene primary amine

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pondering-soul
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#1
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When the H atom seperates (and gives it's electrons to N+ to make it neutral) an RNH2 molecule joins it. This would be the benzene amine right? IDK how to call it but basically it would be like C6H11+ ion right? and then would react with the CL- to make C6H11 + CL- ionic compound?
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charco
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#2
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(Original post by pondering-soul)
When the H atom seperates (and gives it's electrons to N+ to make it neutral) an RNH2 molecule joins it. This would be the benzene amine right? IDK how to call it but basically it would be like C6H11+ ion right? and then would react with the CL- to make C6H11 + CL- ionic compound?
I guess you mean the reaction between phenylamine and an acyl chloride?

PhNH2 + RCOCl ==> RCONHPh + HCl

Not sure where your C6H11+ comes from ...
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pondering-soul
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(Original post by charco)
I guess you mean the reaction between phenylamine and an acyl chloride?

PhNH2 + RCOCl ==> RCONHPh + HCl

Not sure where your C6H11+ comes from ...
ok so im lost.

acyl chloride and primary amine gives a secondary amide and also an amine salt? (ion made from the amine)

so my thinking was that the acyl chloride in the question reacts with the primary amine (phenylamine correct?) to make the said product RCONHPh and then also a H+ ion, which reacts with the amine salt (because that's how chemrevise is saying it goes? or am i lost) and the amine salt has to be PhNH3+ as it joins with this H+ ion released.... this ion then reacts with CI-? Im probably waaay off but can you correct me where my thinking has gone wrong?
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charco
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(Original post by pondering-soul)
ok so im lost.

acyl chloride and primary amine gives a secondary amide and also an amine salt? (ion made from the amine)

so my thinking was that the acyl chloride in the question reacts with the primary amine (phenylamine correct?) to make the said product RCONHPh and then also a H+ ion, which reacts with the amine salt (because that's how chemrevise is saying it goes? or am i lost) and the amine salt has to be PhNH3+ as it joins with this H+ ion released.... this ion then reacts with CI-? Im probably waaay off but can you correct me where my thinking has gone wrong?
The second "reaction" is simply the interaction between excess amine and the acidic medium. All amines form salts with hydrogen ions. However if the reaction mixture is 1:1 then there is no amine to react with the hydrogen ions produced.

The chloride ions do not "react" with anything. They are the balancing ions that go on to form the ionic compound when the solvent is removed.

It's strange to give a reaction scheme that assumes excess amine - you may as well just neutralise the amine directly with HCl.
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pondering-soul
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(Original post by charco)
The second "reaction" is simply the interaction between excess amine and the acidic medium. All amines form salts with hydrogen ions. However if the reaction mixture is 1:1 then there is no amine to react with the hydrogen ions produced.

The chloride ions do not "react" with anything. They are the balancing ions that go on to form the ionic compound when the solvent is removed.

It's strange to give a reaction scheme that assumes excess amine - you may as well just neutralise the amine directly with HCl.
ohh ok that makes sense... but.. if the reaction is 1:1 and there is no amine to react with the H+ ion, why does a mysterious "RNH2" react with the H+? where has it come from and what is it supposed to be?
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Plantagenet Crown
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(Original post by pondering-soul)
ohh ok that makes sense... but.. if the reaction is 1:1 and there is no amine to react with the H+ ion, why does a mysterious "RNH2" react with the H+? where has it come from and what is it supposed to be?
In a 1:1 reaction there would be no mysterious RNH2 around, that's the point. It seems you've provided one reaction but then provided a different reaction (one where 2 eq. of amine are used) to demonstrate the mechanism.
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pondering-soul
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(Original post by Plantagenet Crown)
In a 1:1 reaction there would be no mysterious RNH2 around, that's the point. It seems you've provided one reaction but then provided a different reaction (one where 2 eq. of amine are used) to demonstrate the mechanism.
huh, I'm pretty sure that's the mark scheme for that question.. maybe its wrong idk
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Plantagenet Crown
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(Original post by pondering-soul)
huh, I'm pretty sure that's the mark scheme for that question.. maybe its wrong idk
The file you linked in post 3 is for another reaction. It's not that deep tbh, in your original question if there's a second equivalent of amine then that can pick up a proton, but it doesn't change the product of the reaction. It just depends whether you're also getting marks for mentioning the salt formed etc.
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