This evening, I went ahead and did some problem sets that I jacked from University of Alberta's Chemistry website, haha. I'm doing these to avoid losing the "mental gear" for chemistry, as I have a lot of school work outside of Organic Chemistry this summer.
So, there were three problem sets I completed:
1. #99 Hydride Reductions - Answers
2. #104 Applications - Answers
3. Optional: #103 C=N Formation - Answers
I recommend doing "Hydride Reductions" and the 2nd half of "Applications". You can definitely try "C=N Formation", but I think their questions were the hardest and their proposed mechanisms were a little dodgy.. use your own discretion.
What I learned from these problem sets:- LiAlH4 hydrides can attack an ester or acid (COOH), while the hydrides from NaBH4 cannot.
- Aldehydes and ketones are more reactive than esters or acids (I assume it's because esters and acids have slight electron delocalization between the oxygen atoms, which creates a negative atmosphere that a nucleophile wouldn't want to come near - and this would explain why hydrides from NaBH4 prefer not to attack esters/acids).
- Refreshed my memory on the formation mechanisms of Enamines (NHR1R2 nucleophile), Amines (NH2R nucleophile), Enols (ketones/aldehydes in acidic environment), and Enolates (ketones/aldehydes in basic environment).
- I learned that I have an issue remembering to protonate the electrophile in acidic environments before the nucleophile attacks.. gotta work on that.
That's all for today, enjoy your weekend!
Today's Tune: Team - Iggy Azalea
(It's a cringe-worthy song, I know - but it's good for doing chemistry to... for some reason)
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