Talk:Oxymercuration reaction

message: The diagram of the acetoxy group is obviously wrong (the carboxyl group erroneously has an oxygen double-bonded to oxygen, rather than to carbon).
I was going to say the same thing, somebody fix this!!
Other than that, in the Regioselectivity and Stereochemistry subsection, the autor is trying to explain resonance stabilization by telling us the following:
"By inspection of these structures, it is seen that the positive charge of the mercury atom will sometimes reside on the more substituted carbon (approximately 4% of the time)"
First of all, the resonance structures are not shown. Therefore, it might be nesessary to draw them. Second, there is no such thing like "4% of the time etc", the resonance sturctures show mere resonance contributors, which is a model for understanding and visualizing the reactive sites of a molecular species. The molecule or ion does not "switch" between those resonance structures. I shall try to correct those errors.
:D'oh, I can't believe I missed that. I've corrected the acetoxy image. I also agree that 4% of the time is vague. I merely mean that the structure has little weight and is a minor resonance contributor because it is comparatively less stable than the other resonance structures. The structure is meaningful only in the sense that it gives the carbon its electropositive character. I'll get to these corrections shortly, with a complete treatment of the resonance effects, if you don't beat me to it. -D. Wu 05:25, 4 April 2006 (UTC)

message: According to the book: Organic Chemistry, fifth edition by Paula Yurkanis Bruice the third step of the mechanism is that another molecule of water attacks a hydrogen of the water group forming an alcohol and the electrons from de bond O-H (the attacked H) are passed to Oxygen.
Either way is correct. The hydronium will get deprotonated by that acetate ion.--Nemsen 01:41, 5 December 2006 (UTC)
thread_title:  Third step in the mechanism for Oxymercuration 

message: I've posted the mechanism for the demercuration reaction. If you have any questions, please refer to the literature that I've cited.--Nemsen 01:44, 5 December 2006 (UTC)
thread_title: Demercuration Mechanism

message: I have only BF3-aether solution. 
I would like to do the experiment.
Shall we buy the reagent BH3-THF in the stores?
The reagent seems to be too dear to a student.  —Preceding unsigned comment added by Me3CBr (talk • contribs) 14:33, 23 July 2008 (UTC)
replies: text: I presume that you are referring to Hydroboration-oxidation reaction, a similar reaction?  If you have BF3.ether, you can prepare BH3 (as B2H6) from it by reaction with NaBH4, then trap it in THF.  See J. Am. Chem. Soc. 1958, 80, 1552, and Organic Reactions 13, 1 (1963) describes the apparatus needed.  However, diborane catches fire spontaneously in air, so this reaction should NOT be done anywhere except a proper lab hood/fume cupboard, and it should only be performed by an experienced chemist.  I'd recommend saving up for some borane.THF, which is safer to work with!  One even safer alternative would be 9-BBN, which you may be able to buy more cheaply than borane from a company like Strem. Walkerma (talk) 03:45, 31 July 2008 (UTC)
thread_title:  Shall we buy the reagent BH3-THF in the stores?