Day Eight: I Had to Wear Legit Goggles

Because the alkyl halide used in forming my Grignard reagent is benzyl chloride:

To the observer who has not taken organic chemistry, this structure means very little and certainly couldn't be dangerous, if it's been entrusted to college students.  In actuality, benzyl chloride is an incredibly volatile liquid that doesn't mind becoming airborne as a vapor.  When that happens, it's very easy for this vapor to localize on one's eyes and cause an irritation - hence, it is called a lachrymate.

Unfortunately, benzyl chloride also reacts very willingly with water to form an alcohol.  One of water's protons is released during this process and can react with the chloride anion that resulted from the substitution.  Hydrogen + chloride = hydrochloric acid...a dangerous chemical to have in one's eye.

For this reason, any time that I worked with benzyl chloride, I kept the fume hood mostly closed and wore legitimate laboratory goggles for protection, rather than glasses.

Aside from that, the Grignard reflux was fairly straightforward.  Granted, every piece of glassware had to be dried in an oven at 100 degrees Celsius for an hour to remove any excess water, but once set up, we were able to mix the alkyl halide with magnesium and ether to form the Grignard agent and then add cyclohexene oxide for the Grignard reaction.

We'll find out how it went when we characterize our products tomorrow!