85. Organic chemistry irony

Busy period. 5 reports due next week, and I've no idea what to do regarding one of the mechanisms of one of my chem report. The title is Synthesis of Barbituric Acid.

There was this other experiment, Synthesis of Knorr's Pyrrole, which synthesis I was going crazy about few days back. But after some tricks, I found the entire mechanism synthesis in the Named Reactions book. Worth my 4 hours plus of researching.

So, back to this dumb synthesis. I've no idea where to start, so I was started with wikipedia. As usual, it wasn't there, so I started branching out, using their references, Googling, and e-journals. And all came to naught.

Then, I was thinking, maybe whoever invented barbituric acid, put his name onto it! Then it'll be in the Named Reactions book! So, back to the Chemistry Library (which apparently boasts as the best chem lib in Aus).

Unfortunately... it wasn't there... But nevamind, I'm in the chem lib, I'm surrounded by thousands and thousands of chem books, surely the mechanism of the synthesis is there. So, I started with simple ones, Organic Chemistry (surprising how many books have this name), and as expected, there's none. On to Advanced Organic Chemistry (authors have no book title creativity).

None as well. So, do some library search database, and yields... nothing! I decided to analyse the molecule myself. Okay... got nitrogen, and oxygen and ring, and called pyrimidione, whatever, I forgot already. So it's off to Heterocyclic Nitrogen Compounds. And as expected none.

Okay... barbituric acid... it's a hypnotic drug, under medicinal chem maybe? And I was off to the medicinal chem section, looking under hypnotic drugs, anti-depressants, and a whole lot more of other crap. And then I came across... Wednesday Night In The Chemistry Laboratory. Wah, seems like some authors do have that streak of horror creativity. The contents are just chem stuff though.

Anyway, I've cleared most sections already and I still can't find the mechanism. Then I was searching through the most tedious part of the research - looking through journal articles after journal articles. From Organic Synthesis, Collection Volume, to German journals, to Heiseishu, and even onto Advanced Heterocyclic Journal. From 1900s to 1980s, all nothing.

Zero, nada, all that crap resulted nothing. I was gonna go find the original article when this compound was published in 1880s when the chem lib librarian decided to offer her help. And she directed me to a book back in the general science library - Hancock (and I'm not interested to hear any more jokes about Hancock). All this was Friday, after 3 or 4 hours.

I decided to give internet a try again, a chance to show it's usefulness in chem again. So, I started off with google, expanding my search terms. This time, going for Sigma Aldrich, Uni of Albama and a whole lot of other unis. And they only give the general step, not the whole mechanism. Damn it. Doesn't anyone in the world publish the whole thing?

And just now, I went to Hancock, and looked through the book. Another Organic Chemistry book. Nothing again. Looking around, I see alot of Organic Chemistry books, so I went through them, from 1950s to 2000s. Nothing as well.

What I got out of all the whole thing was nucleophilic acyl substitution and base-catalysed condensation reaction, which I already knew! So, I decided to go back to the start, the textbook. The Organic Chemistry. Since the book was in the reserve section, I made my way there. On the way, seeing another Organic Chemistry book which I've never touched before, I took it with me.

So I sat there, looking through ester synthesis, diethyl malonate synthesis, nucleophilic acyl substitution, base-condensation reaction, ester reactions, acidity, and a whole lot more crap. Finally giving up, I closed both books, and sat down, looking at the shelf in front of me. And I saw it. A book that says Student Solution Manual for one of the Organic Chemistry surrounded by Introduction to Organic Chemistry books. Who knows, it's may have what I want.

Not putting much hope on it, I reached for it, opening it... and nothing. Looking around, the only books I have not touched are those Introduction to Organic Chemistry. Oh well, why not? So I took them, and search under barbituric acid at the index pages.

Well, there's barbiturates, close enough, and I used that alot in all my previous searches. And it was a question. Design the synthesis for this barbiturate. And I'm like wootz! I found it! Now, where's the bloody Student Solution Manual for this Introduction to Organic Chemistry? Grabbing it, I turned to the solution page, and voila! The whole mechanism was there, in front of my eyes. It was as though I found gold!

After 7 hours of searching, I found the mechanism, at a Introduction to Organic Chemistry book. A first year uni book.