I just finished my last day of lab last week, and it was just the way it should have been. But let's start with the long and dramatic backstory:
In Ch 5a (a lab class on advanced synthesis techniques), we have spent all term making estrone, one of the three types of estrogen. Here's the structure (courtesy of Wikipedia):
Estrone is a steroid, for which the three 6-carbon rings and single 5-carbon ring is characteristic. We started our experiments with 6-methoxy-1-tetralone, shown below:
The synthesis was originally composed of seven steps that spanned a month. Instead, our brilliant TAs discovered a shortcut step that took us from step 3 to step 7. I had been on track to finish on Monday. How naïve of me to think that chemistry could let go of me so easily. Even from before day one in Ch 3a (the introductory lab course of which now I'm a TA), I had been the clumsy sort of student whose gloves were ill-fit and couldn't seem to hold tightly enough onto glassware... I'd always remember to wear long pants and close-toed shoes but then arrive at lab to realize I had forgotten a hair tie (I think labs should have extras lying around).
So when I thought I'd finish on Monday, I was too optimistic for my own good. After I finished the last reaction (step 7 but actually step 4), I loaded my crude product onto a silica gel column for flash chromatography. I collected test tube after test tube of eluent (what chemists call the liquid that drips out) and analyzed them using thin-layer chromatography. Below is a video of what the column looks like:
And here's how to collect eluent from the column:
And my finished product! It was a colorless/white solid, just like it was supposed to be (:
So without further ado, a life in the day on February 10, my momentous last day as a lab student:
8:00 - Alarm goes off. For especially rough mornings, I use a sleep tracking app that allegedly monitors my sleep by detecting motion. It draws cool REM cycle graphs and wakes me up when I'm in a lighter sleep part of the cycle.
8:10 - That doesn't mean I get out of bed right away, though... Maybe I'll stretch for a few minutes. It's been raining a lot (yay) lately, and that makes getting up even tougher.
8:22 - Finally get changed (long pants and closed toe shoes!) and head to the campus cafe, Red Door (named such because, well, it has red doors). This morning in particular, I had made plans to meet up with some friends and an alumnus named Tim from '08 who had stopped by to visit the Caltech Christian Fellowship the previous night to share about his current mission work in Ethiopia where he teaches biomedical engineering. If you look up old Fluid Dynamics videos, he beat-boxed a lot. We were meeting him that morning because he had some coffee beans from Ethiopia to share (:
8:40 - After I've finished half my medium chai soy latte, we've gotten the beans and I've done my morning devotionals. I'm currently going through the book of Jeremiah. Red Door's also a good place to read the daily USA Today and watch the news.
9:07 - Finally pack my things and head to lab. Normally for this class we've been starting at 10 am, but I have something for my gothic fiction class later in the day, so I want to get a head start.
9:16 - Of course I'd forget my hair tie. When I was a frosh, maybe I thought I'd be a competent chemistry student by the time senior year came around... but some things never change. Fortunately, I've learned (recently) that if you snap off the glove part of a blue nitrile glove, the band that goes around the wrist makes a decent hair tie. The last reaction of this project is one with estrone methyl ether and pyridine hydrochloride under heat at around 165°C. It replaces the methyl ether with an alcohol. The final product will be washed with aqueous solvents to remove ionic impurities and then purified via flash chromatography (see videos above). For now I just set up the reaction and let it run.
11:08 - I stop the reaction after an hour, let it cool, and then rinse the organic phase in a separation funnel. Since the dichloromethane in that layer is denser than water, the organic phase (and product) were on the bottom. After washes with dilute HCl and deionized water, I used thin-layer chromatography (TLC) to double-check that my product actually was in the organic phase.
12:10 - My gothic fiction class is going on a field trip to the Huntington. I grabbed a pack of Lunchables (the turkey and cheddar is my favorite, but I should try the other two available in the C-store) and a berry parfait and headed to my car so I could get there a little earlier. Most of the class is taking the bus that our professor had arranged for us.
12:30 - I get to the Huntington and eat my lunch in the car because it has started to rain again. The rain really has been just on and off these days... The mountains look a lot greener (: After lunch, I grab my ticket and head to the Japanese garden.
13:00 - I meet up with the professor and the rest of the class to go see some gothic artwork that's in the Huntington archives. We see three William Blake paintings/prints. Sometimes he made a print and then painted more on top of it so that each one was a monoprint (can't be replicated like the typical print).
14:22 - We leave the Huntington as the rain falls heavier. On the way out, we stop by the Orbit Pavilion. No one's there in the rain, so we have it all to ourselves.
14:40 - As soon as we get back to campus, I head back to lab to run my column. I forget to clamp my solvent reservoir on top (the large round glass bulb on top of the column), and when I hook it up to air to push the eluent through faster, the bulb pops off and falls down into pieces. Luckily I was okay, and the solvent it contained was not terribly toxic... The TAs are super helpful and pretty soon we get things back on track.
19:00 - Lab is finally finally done. After I collected the tubes of eluent from the column, I tested them and combined the tubes with product into a giant flask and evaporated the extra solvent. The final estrone product is shown in the video above. Using the NMR (nuclear magnetic resonance) spectrometer, I verified that I did indeed have estrone via 1-proton and 13-carbon NMR spectroscopy.
19:07 - I make it back to Avery just before Norma (the super nice woman who has worked in Avery kitchen for dinner everyday since my freshman year) is getting ready to close the doors. (Dinner usually ends at 7.) She asks Cesar (he used to work in the South House kitchens but recently started working up in Avery) to get a to-go box for me. He scoops up three large servings of chicken and enough asparagus to feed an alley of people for me. Ah, Norma and Cesar are super generous and always make sure I eat my veggies. I'm usually better at asking for smaller portions, but I'm a little breathless from hustling back home in the rain...
19:20 - Daniel messages me to remind me that I had promised to cut his hair. We meet in the Alley 2 bathroom. I've done this once before, a few weeks ago, after watching just one video on Youtube. Thankfully it turned out well enough that he asked me for the favor again. I'm more confident this time but a little less pleased with the result (I was trying to imitate a different style). He likes it, though, and that's all that matters. (:
20:40 - I finish up and we clean all the hair bits as best as we can. Then I head down to the gym for my friend's hip hop class. Dance show is early April, so we've been learning choreography little by little since start of the term. The song of the day is Beyonce's Formation. The dance is quite fast-paced, but we practice it enough times that it starts to feel familiar. By the end of the hour, we look pretty decent. I leave as soon as it finishes because a cappella rehearsal has been moved to today from Tuesday because of midterms week.
22:17 - I'm late and out of breath... for acapella, we encourage punctuality by doing a pushup for each minute we're late. These last few rehearsals are critical, since the Disney show is in a week.
23:43 - Rehearsal is over, for better or for worst. We've learned six songs in as many weeks, and at some point we started to disagree on priorities. We all want to do our best... and you can always get better... But at this point I'm not sure what sorts of things to focus on. Do we want to perfect our sound? Do we want to improve our stage presence? What should we do so we don't look as nervous as we feel on stage? Ah, no matter. John is hungry and wants to go for a midnight snack at our usual go-to, 101 Noodle Express. It's been a long day, and I just want to get off campus and not be around people for a little bit... so I go, even though I don't plan to get anything.
01:19 - The drive was nice, and the restaurant pretty quiet, since no one else gets food at midnight. I'm surprised there are even places open at midnight. It'll be tough to live anywhere else--what other cities in the US have places with quality Chinese food open so late? (Please actually do share in the comments; my stomach and I would love to know.) Over a hearty bowl of noodle soup for him and some mango green tea for me, our conversation goes from all the dumb things like nostalgia for Captain Underpants books to how John felt really lazy all day to how exciting and scary it was for the Pipettes to sing at Disney soon...
I still have to write my report, but I'm glad to be done with lab classes for now. I started out pretty clumsy, but I think, as a retrospective senior, that I have made some progress at the balancing act that is time and hood-space management in chemistry lab, and the greater balancing act that is life at Tech. As I finish up senior year, there'll be so many more last moments to come. Oh, how bittersweet.
keep lookin' up,