Dr Petersen,
I wanted clarification on the example you did in class today:
For the example involving the conversion of butanol to butanal using chromic acid, I realized in my notes that we arrived at a diol by adding H+/H2O. I am trying to figure out the mechanism for the reaction, can you please explain to me?
I would also appreciate it if anybody can help me.
I think that the H+ was used to protonate the oxygen. The extra electrons from the former C=O double bond went to claim the H+ ion. H2O was added to the carbon (now a tertiary carbocation?) and then deprotonated by another water.
ReplyDeleteHowever, if I am wrong, I would love for somebody to explain it to me as well!
That part of the mechanism is material from the end of the semester (maybe chapter 18). But you would first protonate the oxygen atom of the aldehyde and then water adds to the carbon atom of the C=OH+ (turns out that carbon is very electrophilic) and the pi electrons move up to oxygen. You will NOT be tested on this (yet).
ReplyDeleteI guess the water that was added later will then be depronated so that the electrons will move to the second oxygen. I think I get it now. Thank you.
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