Walking myself cool
Mar. 16th, 2006 13:15Well, as exams go, that one was actually not terribly painful. Rushed, yes; I missed 8 points outright because I didn't have time to look at two problems. But I knew most of the rest, and I actually enjoy doing synthesis puzzles.
There's one where I'm pretty sure Tish is going to look at it and say "WTF?", but to the best of my knowledge, it would work. I just have this little feeling that I kind of did it backwards (she likely expected Tab A into slot B, while I figured out how to do Tab B into Slot A). Doing it again here at home reinforced that feeling... but hey, there's more than one way to eat a Reeses.
There is only one person on my friends list who I know would understand the gory details...
firestrike, have a look and see how you'd tackle this one. :)
The problem:

My solution:

As I wrote it on the exam, I used the one-step mechanism to make benzylic acid (the ripping sound you hear is me saying airily, "oh, that's one more carbon than I need, let's get rid of that"). I'm not entirely certain that KMnO4 is that assiduous about oxidizing, but she did tell us it oxidizes everything... if that doesn't work, I could make it into the alcohol first, then rip off the alcohol with KMnO4.
Which is the idea that really made me think that I did this backward -- as I converted one of the reactants into the other. It would have truly appealed to me to show that I didn't need both reactants, but she probably would have marked me down if I didn't use the second one... oh, well, this is all hindsight anyway.
Rip off one carbon, tack another on by CN, I'm virtually sure she had something else in mind but I can't think of what it would be. Probably needs fewer steps, though. :)
Anyway. I think that I was pretty spot-on with the problems I did have time for, and my equilibrium is restored. I don't have any chem homework for this weekend (the payoff for the pain of the exam), and all I have to do for English is do a little Internet research and annotate an essay. Finally, a low-stress weekend!
I'm almost done with the second sock, too. I need to find another knitting/crochet project...
There's one where I'm pretty sure Tish is going to look at it and say "WTF?", but to the best of my knowledge, it would work. I just have this little feeling that I kind of did it backwards (she likely expected Tab A into slot B, while I figured out how to do Tab B into Slot A). Doing it again here at home reinforced that feeling... but hey, there's more than one way to eat a Reeses.
There is only one person on my friends list who I know would understand the gory details...
The problem:

My solution:

As I wrote it on the exam, I used the one-step mechanism to make benzylic acid (the ripping sound you hear is me saying airily, "oh, that's one more carbon than I need, let's get rid of that"). I'm not entirely certain that KMnO4 is that assiduous about oxidizing, but she did tell us it oxidizes everything... if that doesn't work, I could make it into the alcohol first, then rip off the alcohol with KMnO4.
Which is the idea that really made me think that I did this backward -- as I converted one of the reactants into the other. It would have truly appealed to me to show that I didn't need both reactants, but she probably would have marked me down if I didn't use the second one... oh, well, this is all hindsight anyway.
Rip off one carbon, tack another on by CN, I'm virtually sure she had something else in mind but I can't think of what it would be. Probably needs fewer steps, though. :)
Anyway. I think that I was pretty spot-on with the problems I did have time for, and my equilibrium is restored. I don't have any chem homework for this weekend (the payoff for the pain of the exam), and all I have to do for English is do a little Internet research and annotate an essay. Finally, a low-stress weekend!
I'm almost done with the second sock, too. I need to find another knitting/crochet project...