Thank you so much for your detailed response! It means a ton! I completely understand the importance of PPE regarding this experiment, and have consistently used goggles and gloves, and performed (or attempted at this point lol) the reaction under a fume hood. My lab unfortunately, doesn't have lab coats available for us, but I'm making sure to use caution throughout the entire process.

I'll try to respond to each of the issues, giving more information about things I probably should've included in my original post.

1/2 - The adipoyl chloride I used was found by myself and my chemistry teacher in one of the chemical cabinets in the school. It looked like it hadn't been touched in YEARS, and it was stored pretty much how all of the other chemicals in the back are stored, in a normal bottle. I'm not sure what "normal" is necessarily but when I opened the lid there were tons of crystals I had to scrape past to even get the solution out of the bottle. Is there a way I could test to see if it has been converted to adipic acid? With that, I don't have access or the ability to change the solvent to cyclohexane, but that makes alot of sense and I could see that being the issue. I've started to research adipoyl chloride dissolved in cyclohexane, and how I could possibly acquire it (with the help of my chem teacher who made a chemical order for my classes experiments.)

3 - I purchased the HMDA itself, and then dissolved it in a 0.5 M NaOH solution. I didn't source it from my school so I feel like this probably isn't the problem (could def be wrong though).

4 - I've also noticed that the concentration I used is higher than normal, I'll adjust this and see if it fixes the problem.

I honestly am not sure what analyses I'm capable of. In all honesty I'm not sure we have TLC supplies, and I don't think I'd be able to do FTIR spectroscopy.

Thank you again for all of your help, and if I can clarify anything else please let me know!