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S N 2 lab today. Preparation of (2-methylphenoxy)acetic acid from o-cresol and sodium chloroacetate. NaOH deprotonates cresol. Add sodium chloroacetate and reflux. S N 2 reaction occurs. Acidify, collect the precipitate, and recrystallize from water. Unfortunately, today’s lab took a really long time. I’m not sure why, but it did.

Anyway, I looked around for cool S N 2 demos… and there really aren’t any. Sure, I can do the Finkelstein at different concentrations and show that one precipitates NaCl faster than another because it is more concentrated. Woo hoo. That’s not very exciting. So I ultimately decided that today’s lab just isn’t going to have anything to do with the S N 2 reaction.

I decided to do the upsidedown thunderstorm. That’s my name. I’ve seen ‘thunderstorm in a test tube,’ but that’s not a very flashy name, now is it?

Here’s the deal: Add a layer of con’c sulfuric acid to a test tube (use all proper precautions for handling con’c acid!). Slowly and carefully add ethanol down the side to create an ethanol/acid biphase (if you leave it sit too long, the acid and ethanol will mix, so don’t let that happen). Add a few crystals of finely-ground potassium permanganate. The reaction occurs, and evolves a gas. The gas bubbles through the ethanol layer and looks like upsidedown rain. After a few seconds, “lightning” appears at the phase boundary, and the sulfuric layer becomes cloudy and purple (the storm clouds…). The ‘storm’ continues for several minutes. Manganese waste should probably not be thrown down the drain, so if you do this, dispose of it according to local regulations.

There appears to be a few different processes leading to ‘lightning’ formation. Permanganate is converted to the exposive Mn(VII) oxide. Additionally, ozone is created. The ozone oxidizes the ethanol resulting in combustion of the organic material. Wikipedia explains:

Concentrated sulfuric acid reacts with KMnO 4 to give Mn 2 O 7 , which can be explosive … Potassium permanganate and sulfuric acid react to produce some ozone, which has a high oxidizing power and rapidly oxidizes the alcohol, causing it to combust. As a similar reaction produces explosive Mn 2 O 7 , this should only be attempted with great care. An approximate equation for the ozone formation is shown below. 6 KMnO 4 (aq) + 9 H 2 SO 4 (aq) → 6 MnSO 4 (aq) + 3 K 2 SO 4 (aq) + 9 H 2 O(l) + 5 O 3 (g)

When I was practicing the demo, I wanted to see if I could scale it up some to make it more visible than just in a test tube. I tried it with about 20 mL each of the acid and alcohol in a beaker. The detonations were sufficiently energetic (and perhaps the ethanol layer was not tall enough) that the ethanol caught fire. I had a cute little ‘sterno’ burner going. For the actual demo, I switched to an Erlenmeyer flask which helped. No fire this time.



Storm In A Test Tube !