[gravity]

Hi,

I got a question concerning the Hofmann-Elimination.

There should be a reaction between:
1. 1,2-Dichloroethane +  Ammonia (aq)  X

2. 1,2-Dichloropropane + Ammonia (aq)  Y

Now X + Y  Piperidine + 2-Methylpiperidine + 2,5-Dimethylpiperidine.
Annotations:
ratio X : Y is 1:1, reaction under influence of OH^-

Now I'm not sure if X is Ethylenediamine or 1-Amino-2-chloroethane.
And I don't know if Y is 1-Amino-2-chloropropane, 2-Amino-1-chloropropane or 1,2-Diaminopropane.

 

Hope you can help me ...

gravity

[gravity]

I guess I got an error in reasoning.

It seems to me, that the reaction between X and Y is not a Hofmann-Elimination.

It may be a normal substitution!?
The OH^- may be used to neutralize the HCl which is formed if 1-Amino-2-chloroetheane and 2-Amino-1-chloropropane or 1,2-Diaminopropane are used.

So the OH^- is an evidence for the previous mentioned X and Y.

If X and Y would be normal amines, the reaction between X and Y would form Ammonia instead of HCl. And the OH^- would be useless.

So, am I right?

gravity