Something’s Funky Here

June 8, 2023

12:03 p.m.

Adams County Police Department

Detective Hardy = DET

Sneha Jayaram = SJ

Cole Springer = CS

DET: Today is Thursday, June 8th, 2023, and the time is currently 12:03 p.m. This is Detective Hardy with the Adams County Police Department. We are currently sitting in Room 241 of the Science Center at Gettysburg College. Also here with me are…would you please state your names for the record?

CS: Cole Springer, I major in chemistry and German studies.

SJ: Sneha Jayaram. Yeah, we’re both chemistry majors. 

DET: You’re both students of this college, correct?

CS: Yes, and we are both doing research this summer under Dr. Funk, a professor in the chemistry department at Gettysburg College.

DET: Thank you. We recently received a report that an instrument-

CS: Machine. There’s a difference.

DET: Sorry?

CS: It’s a machine, not an instrument. An instrument is essentially a measuring device, while a machine simply performs a mechanical task.

Exhibit 22: An image of a Nuclear Magnetic Resonance spectrometer (an instrument)

DET: Alright, then. We’ve received a report that a machine in your laboratory has gone missing. Could you please explain to me what exactly this machine looks like and what its function is in your lab?

SJ: It’s a rotary evaporator. We use it to isolate products that are dissolved in certain solvents. I have a picture of it, if that would help?

DET: Certainly. For the record, this is Exhibit 23A and B.  

Exhibit 23A (above): An image of the rotary evaporator setup.

Exhibit 23B (below): A video of the rotary evaporator in use.

DET: We received note of the theft on Wednesday morning, the 6th of June 2023. Do either of you recall when you last used the instrument?

CS: I had to use the instrument to evaporate off some chloroform to get an accurate mass of the product I was isolating. That must have been around 3:30 p.m., as my days are pretty structured and I’m often doing the same things at around the same times every day.

SJ: I was probably the last one to use it, then. I remember having to finish the work-up for a column I was running. This would have been around…4:45 p.m.? We left together at five. Professor Funk prefers that neither of us stays in lab alone. Safety, you know.

DET: A column, you say? 

Exhibit 24: An image of a typical “column”

CS: It’s just a technique we use to purify crude reaction mixtures. It separates the compounds into fractions based on their polarities, and then we can easily collect the fractions that contain just our desired compound.

DET: So we have a window for the theft from anywhere between five in the evening to seven in the morning? Wonderful.

SJ: Well, the door is usually locked around five onwards when the last person leaves. Professor Funk left a bit earlier that day, I think. Maybe around four? The door is self-locking, so all we did was close it, really.  

DET: And who holds the keys to the lab?

SJ: Just Professor Funk. I think he may have spoken to you earlier to report the theft? 

DET: That’s right. Are you certain no one else has a copy? There were no signs of a break-in. 

SJ: As far as I know, his is the only one. Although you probably should check with him to be sure. 

DET: Alright, moving on. Did you notice anything out of the ordinary that day? Anything at all?

CS: It was a pretty standard day, I think. We each started out by setting up a reaction when we came in around 9:00 a.m. In short, we measure out how much alcohol we’ll need for the reaction, then create a setup where the reaction flask is under an atmosphere of nitrogen. Unfortunately, oxygen present in the air can lead to unwanted side reactions. If I had set up a reaction the previous morning, I would then work-up–

DET: Hold on a second, did you say you work with alcohol? I feel like this is a very different case if moonshine production is involved.

CS: No, no, an alcohol is simply the general name for a carbon atom connected to an oxygen-hydrogen bond.

SJ: It’s quite simple, really! Do you have a pen and paper? I can draw it out for you. 

DET: Um…sure. 

Exhibit 25A: A picture of the drawing that SJ created for Det. Hardy.

SJ: This right over here is ethanol. It’s what people commonly refer to as alcohol, but it’s definitely not the only one. As long as there’s an OH group in a carbon chain, basically, those interlinked Cs you see over here, you have an alcohol. 

CS: Exactly. Our work is converting these types of molecules, of which there are many, into another, an aldehyde or ketone. These molecules contain a carbonyl, that is, a carbon atom connected to an oxygen atom with a double bond. 

SJ: Oh, and here’s what a carbonyl-containing molecule looks like. The conversion of an alcohol into an aldehyde or ketone is called an oxidation. It’s quite a neat little reaction. 

Exhibit 25B

DET: I think we’re getting off track–

CS: And while there are several ways of doing this type of reaction, our project’s goal is coupled with the idea of green chemistry. This section of chemistry deals with making chemistry more environmentally sustainable by producing less toxic wastes and simply, less waste. So, a catalyst, which helps speed up a reaction–

DET: Please–

CS: –is used alongside a sustainably sourced compound, called furfural, to do these types of reactions. It’s also important to note that our catalyst is made from iron, which is both earth abundant and produces non-toxic byproducts, which helps promote the green chemistry aspect of our research.

SJ: And the mechanism behind these reactions is pretty neat. Here, I have this handy figure here that describes everything perfectly.

DET: This really isn’t necess–

Figure 1: The catalytic cycle of the (tetraphenylcyclopentadienone)iron tricarbonyl catalyst.

SJ: Looks like something out of a horror movie, right? Let me walk you through it. A represents our iron catalyst. It’s inactive, so it can’t do any chemistry yet. But look! If we add some trimethylamine N-oxide (that’s the Me₃NO up there), we remove one of the carbonyl ligands to generate our active catalyst C. You might be wondering about B, but it’s simply a resting state for the catalyst where it’s associated with trimethylamine before it enters the catalytic cycle. Let’s focus on C. So you can see that iron has an empty coordination site, right? A hole to be filled, if you will. It’s this empty coordination site that allows the iron catalyst to oxidize an alcohol–it takes a hydride from the carbon bonded to the hydroxyl (remember, that’s an OH!) group to fill that hole, while the oxygen up on the cyclopentadienone ring takes the proton of the hydroxyl group. It’s negatively charged, you see, so it wants something positive to balance that out. Now where does the furfural come in, you ask?

DET: I didn’t. 

SJ: Well, our iron catalyst now exists as an iron hydride, and we need to regenerate that empty coordination site for it to oxidize another molecule of alcohol. Here comes furfural to save the day. It undergoes the exact opposite of what was done to our alcohol molecule, a reduction. The hydrogen of the iron hydride, along with the hydrogen on the hydroxyl of the cyclopentadienyl group are lost in this process, regenerating C. And this is why it’s called a catalytic cycle. As long as you have enough furfural and the starting alcohol, the reaction can go on indefinitely, in a never-ending cycle. 

DET: Yes, thank you for that illuminating lesson, but can we please get back to the theft? Now where was I? Right, did you guys notice anything out of the ordinary? And keep your answers to ten words or less, for the love of god. 

SJ: Nothing that I can recall.

CS: No, it was just another day in paradise.

DET: So, I guess nothing useful was learned from this conversation.

CS: That’s a lie, you learned a lot about organic synthetic chemistry! 

DET: And had so much fun doing it. You do realize that without your little machine, you can’t continue your research. 

SJ:  We do have another rotavap here in the lab. Though we would really appreciate you finding the stolen one. Do you have any leads?

DET: As much as I would love to pin this on you two for wasting my time, the investigation is still ongoing. 

CS: Well, you know where to find us if you make any progress. 

SJ: Good luck on your investigation!

DET: I’ll be in touch. Right, the time is 1:23 p.m., and this concludes the interview.

The Funk Lab (from left to right): Cole Springer, Professor Timothy Funk and Sneha Jayaram