My junior Joawen asked me a Q on Friday on what can a chemist do in order to obtain most of the product in the enol form. From chemistry, H-bonding with a substituent at the ortho position should be able to stabilize it. -NH2 or -NO2 will be good but not sure which is better since both of them have very different nature. I told Joawen that I'll do some calculations to confirm and my calculations showed that NO2 will stabilize the enol by 4 kcal/mol and NH2 will destabilize it by 4.8 kcal/mol. I thought this is a rather interesting problem and I went on to do calculation for substituents such as Me, CF3 and Cl. All of them showed that keto is more stable and therefore, the NO2 should stabilize it by H-bonding (and maybe something else).Then today, I told my boss and he asked me to check literature to see if anyone has done it as he is sure that someone has already done something similar. I have already checked and the result is negative. Later on, he came to the lab and dicussed with my other seniors on their project. When I told him about it, he told me that since a prof set this Q, surely he must have some supporting data (most likely literature). But no lor, I told him there is something call hypothetical Q or open-ended Q. Then he rebuked me and say if the prof himself also don't know the answer, how to set Q? Then I told him that as long as the students' answer are reasonable, why not? Then he don't believe lor. He "challenged" me and said if you didn't do calculation, will you know the answer? I told him that I did calculation to verify my chemistry. He went on further by drawing nitrobenzene and aniline and asked me, from my chemistry, which will have a lower hydrogenation energy? I told him use nitrobenzene as EWG made it more stable and etc etc. Then he said very hard to say lor and then said may involve aromaticity as well etc. Ahhh. Crab lor.
Pissed.
1 comment:
You know he is old style. Sometimes you just have to do your own chemistry in your group independently...
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