conversion of amine group to halide

[roya]

I'm wondering about the mechanisem of conversion of amine to halide with NaNO2, KBr, H2SO4.

I appreciate your assistance,

[hypervalent_iodine]

Do you mean conversion of an amine to an alkyl halide? Looks to me like you're forming a diazonium salt with the NaNO2 and H2SO4 (though, normally you see HNO2 used). Then it's just a nucleophilic substitution. You see this a lot in text books being used on aromatic systems.

 

If you want pictures, you should look up amines on wiki and scroll down to the reactions to form the diazonium salt and then click the diazonium link to see the nucleophilic substitution mechanism.

 

Hope that helps.

[roya]

Thanks, you're right but the structure I'm concerning about that is not aromatic, it is L-aspartic acid, and I'm wondering if this reaction will be happened in this case.

 

 

 

 

Do you mean conversion of an amine to an alkyl halide? Looks to me like you're forming a diazonium salt with the NaNO2 and H2SO4 (though, normally you see HNO2 used). Then it's just a nucleophilic substitution. You see this a lot in text books being used on aromatic systems.

 

If you want pictures, you should look up amines on wiki and scroll down to the reactions to form the diazonium salt and then click the diazonium link to see the nucleophilic substitution mechanism.

 

Hope that helps.

[hypervalent_iodine]

It should do, yes.