[acidpants]

Hi. I'm an organic chemistry grad student, a bad one. Classes and TAing has been fine and fun,  but I’ve had tremendous difficulty with research. With only two semesters left in my grad career, I have only about 20% of what I need to get accomplished actually completed. As is the nature of research, experiments often do not work. However, I feel I am not learning from my mistakes as should be the case. After discussion with my prof about how to proceed the answer is simply, “just try something else.” I am becoming more frustrated and uninterested in my topic my education progresses. Basically I am looking for perhaps a little inspiration and some reading material on how to get things done in a laboratory setting. I get along great with my prof, but I have never seen her work on her own research in the lab. We are a somewhat smaller school, and I dont believe I can approach other PhDs for advice on my research without her finding out.

Recommended websites or books with advice for organic synthesis or other general wet chemistry practices would be appreciated as well.

Thanks

[Mitch]

There are books on organic laboratory techniques, if that is what you're asking. Have you had a vacation in a while? It might just be a case of burning out which happens to all of us near the end.

[stewie griffin]

If you just need books on how do to reactions, check out "Advanced practical organic chemistry" by Lygo.
Are you just not doing experiments at all?
If you need motivation, well... I think there's alot of others in your boat. My first year in lab was spent on finding a cool route towards a complicated natural product. The nascent methodology never worked on my actual substrate but only test substrates. I was miserable. I gained about 10-15 lbs b/c I had stopped working out and my life became consumed with thinking about my project. I eventually showed that it wasn't going to work out like we wanted and was able to move on to another project. Still hit troubles now and then (like now  ) and I (as others I know) have our good happy weeks and our pissed off depressed weeks. It helps that I can have a good laugh with my labmates and I set aside more time for me now than I used to (go to the gym, run, simply relax and do nothing, etc). Some people frown upon having a work-life balance but it's a must to survive grad school. Like Borek says, maybe a vacation is overdue.
BTW, when it comes to experiments, it's not about the number of reactions run but about setting up the right experiments (the ones where you will learn something from the reaction). Try to only set up reactions where you will definitely learn something for the time being and hopefully you'll either see progress or find that the project just isn't meant to work. It's not easy setting up "good" experiments, but hopefully your prof would be willing to help you judge which reactions are of higher importance. Set up controls alongside reactions that you think "should" work but just aren't. That way if the control works but your desired reaction doesn't, well then maybe you need to modify your starting material or try a different route.
Lastly, if you enjoyed teaching, why not go towards teaching. Ask if you could shape your degree as more of a teaching degree than a research degree. Perhaps you could teach a few weeks of the undergrad organic class, or even some gen chem.

[movies]

This is a very important topic and I am glad someone posted about it.  When I was going through tough times in grad school, I remember one thing that my dad told me about his experience pursuing a masters degree in history: grad school is supposed to be hard!  I think that this applies even more in chemistry where the time commitment (as in time at the lab) is so much greater than in other disciplines.  I even found it difficult to relate with other grad students in other fields where they have much more flexible work schedules.

Personally, I had a very similar experience to what stewie described in the first ~2 years of grad school – I stopped playing sports, gained weight, and was generally unhappy even though I had enjoyed learning so many new things.  The 2nd/3rd year was a real turning point for me as I adjusted to doing only research and essentially no classroom learning.  It is a lot tougher than I ever expected and it wasn't until I felt comfortable teaching myself through reading journal articles and talking with coworkers that I was able to advance my research projects and regain some enjoyment.  I also decided that I was going to pick up some sports again so that I would have something to look forward to each week.  Soccer on Friday nights and racquetball on Wednesdays made all the difference for me.

As far as research goes, it can be very frustrating when you hit that wall and can't seem to progress any further.  As difficult as it sounds, that is really the time that you need to work the hardest.  I completely agree with stewie's suggestions to run some control experiments alongside your "regular" reactions.  Make this part of your standard operating procedure.  Controls are indispensable and then when you are discussing the problems you are having with a particular reaction, you have something to say about it based on the controls.  Nothing is more frustrating to me than hearing someone say "this reaction didn't work" when all they did was lift one particular set of conditions out of a literature paper.  If you do the control experiments at the same time then you force yourself to deconstruct the reaction and get some insight.  When you see reagents over an arrow, ask yourself what the function of each ingredient is in that reaction.  Once you have a "library" of reagents in your head, then you can start mixing it up and varying conditions to solve the problem in your research.  Remember that the conditions you see in other publications are probably optimized for that particular system and not yours!

Use your advisor to help you to gauge what you need to get done in order to finish your project & graduate.  It is her job to guide you and, most importantly, to help you interpret your results.  Other members of your thesis committee are probably willing to help you as well.  There were people in my lab who essentially got a "to-do" list from our advisor every week.  That is okay, but once you start thinking about what is going on in your reactions, you should be able to generate your own list!

Those are some pretty general ideas, I guess, but I hope that it is helpful to you.

[da692]

what exactly have you been doing? to fly under the radar for this long (with only 2 months left to finish) at the graduate level is irresponsible of you and your advisor. Is your advisor pushing you? are you pushing yourself? nothing will ever get done if you stay within your (and i hate to say it) comfort zone. nobody goes through their career (chemistry) as a graduate student, or professional, without these ups and downs. synthetic chemistry is a hard life and you have to want it. shoot, its hard to stay encouraged when 2% of research steps work-unless you're one of those methods guys. keep plugging away, it doesn't seem like you have the time for a vacation at this point. best regards

[stewie griffin]

Re: da692 
While it is true that acidpants doesn't have much time to waste (and thus probably not enough time for a true vacation), I don't appreciate your automatic assumption that because this student doesn't have many research goals completed that they must not have worked hard enough. It is precisely this attitude that pisses me off more than anything in the world of organic chemistry (sorry for the language). Organic synthesis guys get such bloated egos with their "oh I work 4,000 hours in one day" and "well Bob over there is a terrible chemist b/c he hasn't even finished a molecule yet" or "oh you only have one paper (or worse, none), well then you sir suck." I busted my butt off for a year and a half for that failed route towards a natural product I mentioned. At the end I didn't have anything to show in the sense of material that would get published, but I learned a hell of a lot, figured out how to set up the proper experiments with controls, and found out how to become an independent scientist (come up with my own ideas, read the literature, teaching myself just like movies said). I think that is far more valuable than having cranked out a paper on easy chemistry. In fact I remember one of the 5th years in my lab (who during her time here had taken up an already started synthesis, and ended up completing it) tell me when I was down and out that I was going to be better off for having struggled through this rather than just be handed chemistry that was meant to work and not learn anything.
Pre-grad school I thought that the harder you work in life the more results you get. In science this is simply not always true. If a reaction simply isn't going to work, then it doesn't matter how many hours you put in, how many variables you change, etc... it's just not going to work. Sure if the chemistry works, then work hard and fly through it. But to assume that not much results = not enough hard work just doesn't follow in the world of science. Perhaps acidpants is totally lazy, but you can't just assume that from their results. If it seems I am being defensive, it's b/c I am. Sure I have results now and have completed a synthesis, but it was tough at the start and it didn't help to have people like you implying that I was a piece of poop just b/c my reactions weren't working.
Ahhh, I feel better now. 

[cth]

Yes, I find the position of Da692 a bit unfair too.
Da692, do you know how much time Acidpants has put in his project? No, just like me, you don't know. Yet, you seem to assume immediately that he is guilty of laziness. That's one step I wouldn't take so quickly. 


Personally, I agree with Stewie: Science doesn't always reward hard work.
When you start a new project, you can't be sure if it is going to work or not. But you have to try to find out...

For young researchers, the number of publications doesn't necessarily reflect the scientific value of a person. If you start a PhD on a difficult project, chances are you will have fewer publications at the end than someone working on an easy one. Unfortunately, afterwards for finding a good postdoc and for your later academic career, the number of publications is critical. Nobody said life has to be fair. 
Remark, it is for senior researchers (who have been working on many different projects, both easy and difficult, over a decade or more) that the publications number starts to be relevant to determine their scientific value: the ups and downs of their career tends to average out, more or less. Before that, the publication fluctuations are too high to be statistically meaningful.


If as a new PhD student, you want to start to publish as soon as possible:
- stay in the same lab where you did your master work and keep working on the same project.
- look for a lab where the research project is near completion and with a postdoc to closely monitor it.

[da692]

I didn't exactly mean it to come across the way it did and some of the implications were unintended. I won't bother with an explanation and will only apologize for the insensitivity, acidpants. Best regards.

[orgopete]

Interesting topic. While working in industry, I saw projects continue for a lack of insight. This is my belief. Every experiment should answer a question. That should grow into a body of knowledge, positive or negative. I am advocating a list of principles to examine, not chemicals. That is how I knew when to move on. I think (or hope) that is the essence of what Stewie Griffin was advocating.

[FlowSyn]

I have 60 days left in my Ph.D. as I'm due to my postdoctoral assignment in April.  I have 2 more publications to write, a plethora of experimentals to finish, and the boss is still throwing work at me - all while I'm mentoring a FES and a FP (foreign postdoc).  Some days I still feel like throwing in the towel and becoming a car mechanic or something.  After going through 1 nervous breakdown in my second year - I learned that this is just how it is and you've got to keep pushing forward.  There is light at the end of the tunnel - a dim one, but it is there.   

[cpncoop]

I think the most important thing to keep in mind while going through graduate school is that the years you are there are a very small slice of your life as a whole.  Keep things in perspective... While publications are important, and it's always good to solve the problem you're investigating, you are preparing for a career that is going to be filled with ups and downs.  You can work for years on a project, make great progress, and have it be killed in clinical trials.  You can investigate a problem for months on end and make no progress - these things happen.  It is important to enjoy the successes when they occur, and focus on the task at hand when things aren't working.  All you can do is try the experiments you think make sense, talk to your colleagues to get additional input, and do your best.  If chemistry was easy, it wouldn't take so long to accomplish things, and if one person had all of the answers, most of us would be out of a job.  Having worked in industry for a while now, the most useful thing I learned in graduate school was how to logically approach a problem, design an experiment, and narrow down the number of possible answers.  If you can do that, you'll be a success.  Good luck, and cheer up..