[hihi]

Hi folks,
I'm in an organic chemistry lab and I've been trying to identify a possible ester compound by synthesizing and extracting the alcohol portion of the ester.

I think I have an ester because all of the basic characterization tests were negative until I did the ferric hydroxamate test which came out positive.

What I did was to use 1mL of ester, a couple drops of concentrated sulfuric acid, and 1g of 3,5-dinitrobenzoic acid. These would be mixed and refluxed at 125 degrees for 1 hour and then extracted out.

But, I still see most of the starting benzoic acid solid in my solution and feel like there was no reaction. There was no color change or a visible decrease in amount of solid in my container. Should I go ahead dissolve the entire thing in ether and sodium bicarbonate for extraction? Did I even get a reaction??       Any ideas would be helpful...thanks!

[TheOrganic]

If you see most of the starting solid benzoic acid unreacted in the solution, then I think it means no reaction has happened. If you are in an organic chemistry lab, then you should sit down and think out the possibilities you went wrong. Try to redo the experiment and evaluate where exactly you went wrong. Clearly giving out an answer will not help. I feel one needs to experience these situations and find out ways out to become a successful chemist.

[hihi]

Thanks!  It helps to just have an idea if I even got a reaction in the first place.

Believe me when I say I have spent the last few weeks researching the heck out of ester derivatives. I'm feeling the pressure now though cause I don't have many lab sessions left before I need to figure it out and we're not given a lot of reagents so I have to use my material sparingly.

[OrganicSyn1.0]

Take a ¹HNMR of starting material and compare it to the spectrum of your current solution. Just look for the appearance of new peaks/differences in chemical shifts. If you dont have access to a NMR spectrometer use a IR spectrophotometer to take spectra of starting material and current solution and look for a change around 1500-1775 cm^-1 to denote a ester compound. Hope it helps!!!

[hihi]

Thank you! It turns out that a reaction did occur so I got my derivative. Like you suggested, my IR verified the compound as well (hopefully).

Cheers!