Deriving Amine Salt: Making Butylamine Hydrochloride Derivative

[Donnikko]

Homework Statement

I have to make a solid derivative of an unknown compound. All the data I have collected points to the unknown being butylamine hydrochloride. My textbook has suggestions for making derivatives of amines, but nothing for amine salts.

Homework Equations

The Attempt at a Solution

I attempted to form an acetamide functional group as directed for a primary amine and I don't think it worked (technically it is supposed to work within 12 hours, but I kind of don't think it's going to). I think what I need to do is extract the amine by mixing my compound with a dilute NaOH solution, extracting the amine layer and attempting to convert the functional group again. Mostly I am just curious if anyone with a bit more orgo experience has any input as to whether I am tackling this in the right way. Thanks.

 

[nate808]

Hello,

Based on the data you have collected, it does seem likely that your unknown compound is butylamine hydrochloride. The first step in making a solid derivative would be to extract the amine from the hydrochloride salt. As you mentioned, this can be done by mixing the compound with a dilute NaOH solution and extracting the amine layer.

Once the amine is extracted, you can attempt to form a derivative using the methods suggested in your textbook for primary amines. It is possible that the acetamide functional group did not form because the amine was still in the form of a salt. By extracting the amine, you will have a free amine to react with the acetamide reagent.

I would also suggest checking the purity of your amine before attempting to form a derivative. If there are impurities present, they may interfere with the reaction and prevent the formation of the desired derivative.

Overall, it sounds like you are approaching the problem in the right way. It may also be helpful to consult with a colleague or your instructor for additional guidance and advice. Good luck with your experiments!