organic chemistry labs

Hi,
Does anyone know where I could find some organic chemistry labs, or ideas for labs designed for an organic chemistry course.
I'm thinking things along the lines of hop oil extraction and the chemistry behind it or different malt things like the production of dimethyl sulfide pre and post fermentation or even yeast things. Getting into biochemistry would also be fine.
I'm a student who, due to my senior project which was to start a beer "CSA," has missed all of the organic chemistry labs this term and now am scrambling to due lab write-ups on things relevant to my education and project.
Any ideas?
Thanks a lot.

You might want to check out the M.I.T. Open course ware, they have basic chemistry to physical chemistry. So I'm sure if you looked hard enough you would be able to find what you are looking for.

here is the link to the home page hope that helps. http://ocw.mit.edu/courses/material...ll-2010/27-introduction-to-organic-chemistry/

Great,
Thanks a lot. I'll check that out right now.

Wait. So you missed a month or two of O-Chem labs, and you school is letting you make them up by writing about beer? Huh.

Well, it's a little more intense than just, "writing about beer," but yes, I am allowed to do the same amount of work as everyone else at a different time to make up for work I missed. It's actually nice to study with people who are down to earth enough to realize that sometimes the curriculum isn't the only way to learn things and are willing to let motivated students pursue other paths that are more relevant to their education.

Yea I must say that would be nice, I'm a chem major and I'm 99% sure my prof's wouldn't let me go out on my own like that. I guess I could do some guided research in beer with one of the o-chem guys but I would rather spend my free time drinking the beer.

Saccharomycetaceae said:

Well, it's a little more intense than just, "writing about beer," but yes, I am allowed to do the same amount of work as everyone else at a different time to make up for work I missed. It's actually nice to study with people who are down to earth enough to realize that sometimes the curriculum isn't the only way to learn things and are willing to let motivated students pursue other paths that are more relevant to their education.

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Where are you currently attending?
~curious middle school educator

Since I never took organic chemistry I don't have any feel for what sorts of things go in the labs but one thing did come to mind: run through the oxidation states of ethanol i.e. add a bit of oxidizing agent to it noting production of acetaldehyde, easily detectable by smell. Add more oxidizing agent and note production of acetic acid - also easily detectable by smell. I suspect this may be too trivial but thought I'd throw it out anyway. Or if you want to stink up the place use butyl alcohol.

To do the same thing with more sophistication you could get one of those low level alcohol test kits that does the first oxidation with NAD in the presence of alcohol dehydrogenase and measures the NADH production by UV absorption and then catalyzes the second step with aldehyde dehydrogenase. Again the increase in NADH can be measured.

^^^ I'm sure he could use the mass spec in the lab

Or even a GC if the lab isn't equipped with MS.

A GC would work but you would need to find a column with right selectivity for the compounds you wish to resolve especially if you aren't using a MSD. With a flame detector, column selection is much more important because there can be coelution and peak interference. If you are lucky enough to find a lab that has a mass spec and you don't have to buy your own column, then you are good to go. But chances are at the very least you will have to buy your own column unless the lab is willing to buy one for you. They start at around $600 and can cost thousands for more specialty ones.

If you have any more questions feel free to ask. I am a professional working chemist and have been doing GC work for close to 10 years now.

Hey there. I am confused at what you needed exactly. Do you need to come up with a short lab project for credit? You mentioned hop oil extraction but there isn't much chemistry there since it is just hop oils dissolving in a solvent.

I had a few things pop up though if you want to do something with hops and chemistry. The chemistry behind the alpha acid to iso-alpha acid isomerization is a cool story to explain to non-beer people for one, but the IBU determination method is very easy to do if you have lab access so you could run a few beers and measure their IBUs. All you do is acidity the beer with HCl to protonate the oils (makes them less water soluble) then you extract with isooctane and read on a UV spec at 275nm. If you have time you could even center the project on beer that has been stored cold vs stored at room temp to compare the IBU degradation. Buy a fresh brewed pale ale six pack, set 3 in a fridge and set 3 out at room temp for a few weeks. Take them into lab, test, drink the rest not used in the assay, pass the course win win.

ColumbusAmongus said:

The chemistry behind the alpha acid to iso-alpha acid isomerization is a cool story to explain to non-beer people for one, but the IBU determination method is very easy to do if you have lab access so you could run a few beers and measure their IBUs.

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I did a similar lab in freshman chemistry. I would hope that organic chemistry is a little more... challenging.

Haha it is but labs have to fit into small blocks of time that students can complete within a week or two so they are a bit over simplified in comparison to real orgo that happens in a research lab. There isn't much you can do with beer in regards to synthesis and purification so the IBU method can teach the principle of extraction, which is a common lab subject in orgo, and then the follows up with a quick quantitation on a UV spec which should be fairly easy to do within a 2-3 hour lab period.

Most of the time in the isooctane method is taken up by 15 minutes of shaking (where the extraction actually takes place) and, if the phases don't separate (and they often don't), with centrifugation to get them to. Thus to do multiple replicates can take quite a bit of time.