Reaction Mechanism

[G1SG2]

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How does the addition of K to (CH3)3COH create t-butoxide? Am I missing something here? Can someone please explain the mechanism? Thanks.

 

[sv3]

How does the addition of K to (CH3)3COH create t-butoxide? Am I missing something here? Can someone please explain the mechanism? Thanks.

seriously? An alcohol and potassium? I have no idea. Perhaps it has to do with the solution the reaction is occuring in? At a loss really.......sorry

 

[G1SG2]

seriously? An alcohol and potassium? I have no idea. Perhaps it has to do with the solution the reaction is occuring in? At a loss really.......sorry

Yeah...that was a Kaplan question.

 

[sv3]

Yeah...that was a Kaplan question.

what is t-butoxide anyway? Three methyl groups and one single lone oxygen atom (thus having a negative charge)?. It's been 10 yrs since i was in first year sciences so the nomenclature still hasn't come back! All I thought was that the molecule is sterically hindered. That's the only thought i have.

anyway no clue! And i went through TPR for orgo and its pretty detailed. That is one nasty question.....i'm hoping it's an error.

gluck

 

[G1SG2]

what is t-butoxide anyway? Three methyl groups and one single lone oxygen atom (thus having a negative charge)?. It's been 10 yrs since i was in first year sciences so the nomenclature still hasn't come back! All I thought was that the molecule is sterically hindered. That's the only thought i have.

anyway no clue! And i went through TPR for orgo and its pretty detailed. That is one nasty question.....i'm hoping it's an error.

gluck

Yeah, t-butoxide is (CH3)3CO-. I've never seen such a reaction either. I don't think it was a mistake, there were two similar answer choices, both with K as a reactant.

 

[boaz]

K (not K+) is a very powerful reducing agent. It donates its electron to hydrogen, forming H2 gas and tert-butoxide. It's a similar mechanism as with other alcohols/water.

 

[sv3]

K (not K+) is a very powerful reducing agent. It donates its electron to hydrogen, forming H2 gas and tert-butoxide. It's a similar mechanism as with other alcohols/water.

What type of mechanism did you mean? Sorry I'm just lost.
Also, does potassium precipitate out then as well?

How would one know K is a reducing agent? Like is there a way to know this intuitively? (anything with an extra electron? as opposed to a halogen which could be oxidizing as it wants to take an electron? I could be way off on a tangent here but trying to figure it out). I remember reading something with lots of Hs is reducing and Os is oxidizing but never saw K.

thanks

Pookiez....sorry for hijacking the thread

 

[G1SG2]

K (not K+) is a very powerful reducing agent. It donates its electron to hydrogen, forming H2 gas and tert-butoxide. It's a similar mechanism as with other alcohols/water.

👍

 

[loveoforganic]

What type of mechanism did you mean? Sorry I'm just lost.
Also, does potassium precipitate out then as well?

How would one know K is a reducing agent? Like is there a way to know this intuitively? (anything with an extra electron? as opposed to a halogen which could be oxidizing as it wants to take an electron? I could be way off on a tangent here but trying to figure it out). I remember reading something with lots of Hs is reducing and Os is oxidizing but never saw K.

thanks

Pookiez....sorry for hijacking the thread

alkali metal, gives up one electron to achieve noble gas configuration. I couldn't find the exact mechanism, but reactions involving alkali metals in organic chemistry tend to proceed by radical mechanisms.

dissolving metal reduction mechanism

http://www.chem.ucalgary.ca/courses/351/Carey/Ch09/ch9-7.html

 

[sv3]

alkali metal, gives up one electron to achieve noble gas configuration. I couldn't find the exact mechanism, but reactions involving alkali metals in organic chemistry tend to proceed by radical mechanisms.

dissolving metal reduction mechanism

http://www.chem.ucalgary.ca/courses/351/Carey/Ch09/ch9-7.html

got it, thanks. Can you use similar reasoning to say halogens are oxidizing? Or am i better off just remembering alkali metals give up one electron.

thanks alot!

 

[loveoforganic]

Yes, the halides (the actual compounds, not the ions, e.g. Cl2, F2) are powerful oxidizing agents. Bromine and iodine not so much, but still to an extent. For example, bromine is used to oxidize a carbohydrate's aldehyde to a carboxylic acid.

 

[sv3]

Sweet. Thanks. Hence O2 being the final electron acceptor in the ETC.

This should have occured to me before but I just figured since O2 and other halogens have their stable octet when diatomic, they would not want to mess with that. But I guess they do.

 

[loveoforganic]

O2 in the ETC is another good example.

 

[sv3]

I guess i'll look at them as being selfish then. Rather be an octet on their own as opposed to sharing...........as long as it makes sense in me head i'll be happy

 

[loveoforganic]

Could you clarify what you're saying? I think you might not have it quite right. The diatomic halogens are powerful oxidizing agents because they'd rather bind a less electronegative atom. This allows them to hold a larger portion of the electrons, rather than an equal sharing.

 

[sv3]

Could you clarify what you're saying? I think you might not have it quite right. The diatomic halogens are powerful oxidizing agents because they'd rather bind a less electronegative atom. This allows them to hold a larger portion of the electrons, rather than an equal sharing.

Got it now, and in a more accurate way, thanks. I was wondering why diatomic halogens were powerful oxidizers if they already got their full octet when bonded together. I was wondering what makes them want to leave this situation. But you just told me.....to have a bigger share of the electrons. Now it makes scientific sense.....thanks!