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Tertiary Alcohols

by GeneralOJB
Tags: alcohols, tertiary
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GeneralOJB
#1
Mar29-13, 04:55 PM
P: 42
I've learnt that tertiary alcohols can't be oxidised because the carbon bearing the OH contains no hydrogen atoms. But why can't the oxygen just take the hydrogen from the OH and another hydrogen from another carbon atom on the molecule?

I also read that it would involve breaking a C-C bond - how so?
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AGNuke
#2
Mar30-13, 05:41 AM
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Alcohols are oxidized to carbonyls (as in organic chemistry). And what are you saying, involving H from Alcohol and H from neighboring C-atom, no carbonyl product can be formed, hence tertiary alcohols are not oxidizable due to the virtue of -OH group being there.

But if you are hell bent to oxidize it, just take fluorine gas, it will break the entire molecule and oxidize it.
ldc3
#3
Mar30-13, 09:31 AM
P: 13
Quote Quote by GeneralOJB View Post
I've learnt that tertiary alcohols can't be oxidised because the carbon bearing the OH contains no hydrogen atoms. But why can't the oxygen just take the hydrogen from the OH and another hydrogen from another carbon atom on the molecule?

I also read that it would involve breaking a C-C bond - how so?
If you took the hydrogen from the oxygen and another hydrogen from a non-adjacent carbon atom, you would then need to connect the oxygen to something and the carbon to something. Also, taking a hydrogen from non-adjacent carbon takes more energy since the oxygen (without a hydrogen) transfers some of it charge to the adjacent carbon, which makes the adjacent hydrogen easier to remove.

Since there are only C-C bonds on a tertiary alcohol (aside from the OH), if the OH is converted to a double bond to the carbon, then a C-C bond would need to be broken (since carbon cannot have 5 bonds).

GeneralOJB
#4
Mar30-13, 01:48 PM
P: 42
Tertiary Alcohols

Quote Quote by ldc3 View Post
If you took the hydrogen from the oxygen and another hydrogen from a non-adjacent carbon atom, you would then need to connect the oxygen to something and the carbon to something. Also, taking a hydrogen from non-adjacent carbon takes more energy since the oxygen (without a hydrogen) transfers some of it charge to the adjacent carbon, which makes the adjacent hydrogen easier to remove.

Since there are only C-C bonds on a tertiary alcohol (aside from the OH), if the OH is converted to a double bond to the carbon, then a C-C bond would need to be broken (since carbon cannot have 5 bonds).
Thanks, I understand now. I never considered that carbon would have to have 5 bonds!


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