Oxidation of -OH (1 Viewer)

Paroissien

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For example when permanganate oxides ethanol:
CH3CH2OH + H2O ---> CH3COOH + 4H + 4e
I don't understand how the -OH is oxidised to form -COOH. I think of oxidation in terms of galvanic cells, and I can't get my head around how this work. Could someone please explain it to me?
Cheers
 

mervvyn

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Oxidation in chemisty means the loss of electrons.

here, look at the CH2OH compared to the COOH. in going from ethanol to ethanoic acid, the two hydrogens are replaced by a double bonded O from the water, leaving behind 4H+ ions, 2 from the water and 2 from the ethanol, plus 4 spare electrons.

NB nothing actually happens to the -OH, it just sits there.

I don't quite know how that's oxidation actually, i spose it is the hydrogens losing their electrons. just out of curiousity, what unit is this from?
 
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nit

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Oxidation in organic chem is slightly different to oxidation in inorganic....in organic chem, oxidation may be considered as the gain of oxygen by a compound / loss of hydrogen, while reduction is gain of hydrogen/loss of oxygen.

Hence in this example the ethanol is oxidised to form acetic acid (gain of oxygen by ethanol), while the water can be said to reduced as it loses oxygen.

If you want something more formal, then you can look at electronegativities (x) in organic chem to assign oxidation numbers, since covalent bonds are considered to be bonds where electrons are shared - ie while there is electron density on the carbons (x=2.1) connected to oxygen (x = 3.5), it can nonetheless be treated as if the carbon atom gave up the electron pair to oxygen.

So, in assigning oxidation states:

for a C-O bond, we assign C the oxidation state of +1, O of -1
for a C-H bond, we assign C the oxidation state of -1, H of +1, as H has x=2.1, C has x=2.5

I'm not entirely sure how to assign the oxidation number for the CH3-C bond, but we'll assume the carbon joined to the OH functional group is more electronegative (either way works)...so for this carbon, it changes from oxidation state of -1-1+1-1=-2, to +2(for the double bond) +1 -1 =2, which accounts for your 4e- out the other end.

Obviously, this is simply a half reaction, and so you'd need an oxidising reagent to cause this reaction to occur - dichromates, chromic oxide, potassium permanganate are all useful here.

BTW, we don't need any of this :)
 

Paroissien

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Thanks very much, both of you, and the oxidising agent I'm thinking of it potassium permanganate

You do (kinda) if you do forensic chemistry. I've seen question asked on this kind of thing, although it is in a far more simplified form. I just like to have the background to the questions. Helps me
 
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