Tertiary Alcohols: Can't be Oxidized & Breaking C-C Bonds

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In summary, tertiary alcohols cannot be oxidized because the carbon bearing the OH contains no hydrogen atoms.
  • #1
GeneralOJB
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I've learned 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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  • #2
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.
 
  • #3
GeneralOJB said:
I've learned 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).
 
  • #4
ldc3 said:
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!
 
  • #5


I can provide some clarification on the subject of tertiary alcohols and their inability to be oxidized. Tertiary alcohols contain a carbon atom bonded to three other carbon atoms, meaning that there are no hydrogen atoms attached to the carbon bearing the OH group. This makes it difficult for the oxygen to take a hydrogen from the OH and another hydrogen from a neighboring carbon atom, as there are no available hydrogen atoms to be taken.

Furthermore, the process of oxidation involves the loss of electrons from a molecule. In the case of tertiary alcohols, the carbon atom bearing the OH group is already surrounded by three other carbon atoms, making it difficult for the oxygen to gain access to the carbon and remove an electron. This is why tertiary alcohols cannot be oxidized.

In terms of breaking C-C bonds, this refers to the process of removing the OH group from the carbon atom. This bond must be broken in order for the alcohol to be oxidized, as the OH group is attached to the carbon atom through a C-C bond. However, due to the stability of C-C bonds, it requires a significant amount of energy to break them. This is why tertiary alcohols are resistant to oxidation and breaking C-C bonds.

In conclusion, the reason why tertiary alcohols cannot be oxidized is due to the lack of available hydrogen atoms and the difficulty in breaking C-C bonds. This is a result of the unique structure of tertiary alcohols and their strong bonds. I hope this helps to clarify any confusion on the subject.
 

Related to Tertiary Alcohols: Can't be Oxidized & Breaking C-C Bonds

1. What are tertiary alcohols?

Tertiary alcohols are a type of alcohol that have a central carbon atom bonded to three other carbon atoms and a hydroxyl group (-OH) bonded to the central carbon atom. This makes them structurally different from primary and secondary alcohols, which have only one or two carbon atoms bonded to the central carbon atom, respectively.

2. Why can't tertiary alcohols be oxidized?

Tertiary alcohols cannot be oxidized because the central carbon atom is already bonded to three other carbon atoms, making it unable to form a stable intermediate for the oxidation reaction to occur. In oxidation reactions, the central carbon atom typically forms a bond with an oxygen atom, but in tertiary alcohols, there are no available carbon-hydrogen bonds for this to happen.

3. How does the inability to oxidize tertiary alcohols affect their reactivity?

The inability to oxidize tertiary alcohols makes them less reactive compared to primary and secondary alcohols. This is because oxidation reactions are a common way for alcohols to undergo chemical reactions and form new compounds. Without this option, tertiary alcohols have fewer pathways for chemical reactions to occur, making them less reactive.

4. Can tertiary alcohols still participate in other types of reactions?

Yes, tertiary alcohols can still participate in other types of reactions, such as substitution, elimination, and addition reactions. However, their reactivity is generally lower compared to primary and secondary alcohols due to their structural limitations.

5. How do tertiary alcohols break C-C bonds?

Tertiary alcohols can break C-C bonds through elimination reactions, where the hydroxyl group and one of the carbon atoms bonded to the central carbon atom are removed, forming a double bond between the remaining two carbon atoms. This type of reaction is often used in organic synthesis to form new carbon-carbon bonds and create more complex molecules.

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