What would you do?

What would you do if you (or a student in your Organic lab) spilled about 150 mL of solution containing DMSO, DME, water, ~6 M HCl, iron (II) chloride and ferrocene all over your lab notebook?

I dunked it in a tub of water with sodium bicarbonate followed by a dunk in clean water. I'll let you know how it turns out. Wrinkly, I'm sure.

UPDATE: Yup, it's wrinkly. Crunchy too, but legible and perhaps usable. The pages are a little brown from the residual iron which I'm sure has settled into a +3 oxidation state.

Midterm exams

It is midterm time. Time for exams.

I'm writing an Organic exam for tomorrow. It covers cycloalkanes and an overview of organic reactions.

Feel free to suggest a question you think I should include on the exam. I'm not opposed to letting other people do my work for me.

Fluorene, what's it good for?

I've been culling items from our organic stockroom. This task has been long overdue. I have bottles of things that were filled before the EPA and OSHA even existed. They were filled before benzene started causing cancer.

I found a 1 pound bottle of fluorene. Fluorene puts the F in FMOC and the F in a lot of other things.

My question is, does anybody know what uses plain, old, ordinary 9H-fluorene has?

I know the proton can be removed relatively easily and then it probably acts as a nucleophile.

It can also be oxidized to fluorenone using a phase transfer catalyst.



What else can I do with my newly discovered stash of fluorene?

What do you want?

So, I've been really bad at posting on this blog. I'm not sure what my problem is. Oh! I know. I've been really busy at work with an impending accreditation review coming up in October.

So much for my summer.

Back in the day when I was pretending to be a premed, I had a med school interview. I was ready to answer all possible questions. So, I was taken aback when the doctor interviewing me asked me, "so, what do you want to know?" That was his first and only question. I didn't expect to be asked to ask questions. Perhaps I was naive. When all was said and done, I went to grad school. However, even before then, I was convinced I wanted to be a chemist. At the time I was just going through the premed motions.

So, I thought I'd ask you, my readers (both of you), what do you want to know?

What do you want to know about brewing beer? About teaching Chemistry? About holding your high school high jump record for 18 years (and running).

I know some things about these areas and will dispense whatever information I have about them free of charge.[1]

So, what do you want to know?

[1] I realize I'm overcharging you, but deal with it!

Methylene chloride

I've always wondered and now I am asking the world: Why does methylene chloride hurt when I get it on my skin? It's especially bad under a ring.

Here's another question, what is your preferred name for CH2Cl2?

Explain this one to me...

In my organic lab this week my students did the classic elimination reaction of cyclohexanol to form cyclohexene. The reaction is easy.


The cyclohexanol is mixed with some phosphoric acid and refluxed for a bit and the cyclohexene product is distilled. A second distillation with a toluene chaser is used to purify the product. I analyzed the products with GC-MS. The GC-MS showed what one would expect a 2nd year Organic lab student to produce: cyclohexene, toluene, and unreacted cyclohexanol.

However, in some product mixtures I also saw a significant amount of 1-methylcyclopentene. The reaction of that is as follows:
My question is, "How does that form?"

Here's a possible mechanism that I think is highly unlikely due to the primary carbocation.
This mechanism moves the atoms to the correct final position, but I find the ring contraction to form a primary carbocation unlikely. Maybe I'm wrong.

Other things: I check the starting material. It was 99.8% cyclohexanol. In the reaction dicyclohexyl ether forms. I'm not sure if this could assist in the rearrangement.

Any ideas?

What's your base bath recipe?

For all of those chemists who read this, what is your preferred recipe for a base bath?

Mine is: dump some KOH into some EtOH. Stir to dissolve. Use.

Not very precise.

What do you use?

[for the brewers who read this, don't worry. I'll have a question for you in a few days.]