Why Can't Tertiary Alcohols Be Oxidized?

In summary, oxidation of primary and secondary alcohols involves breaking a C-H bond, while oxidation of a tertiary alcohol requires breaking a C-C bond which is energetically unfavorable. Therefore, the presence of a C-H bond allows for oxidation to occur in tertiary alcohols.
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I’m still a relative newbie to chemistry so if this question is very simple to answer I apologise….. but what prevents the oxidation of a tertiary alcohol cause you can form an aldehyde and carboxylic acid from a primary alcohol and a ketone from a secondary but what is it that prevents a tertiary alcohol oxidising????
 
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Oxidation of primary and secondary alcohols require what is in essence the breaking of a C-H bond. Oxidation of a tertiary alcohol would require the breaking of a C-C bond.

Energetics strongly disfavor the latter process.
 
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Hyperfine said:
Oxidation of primary and secondary alcohols require what is in essence the breaking of a C-H bond. Oxidation of a tertiary alcohol would require the breaking of a C-C bond.

Energetics strongly disfavor the latter process.
Ahhhhhhhhh so it’s just the presence of a C-H bond which allows oxidation to occur obviously in tertiary the OH group is attached to a carbon bonded to 3 other carbons, ok ok thank you
 
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FAQ: Why Can't Tertiary Alcohols Be Oxidized?

What is the general reaction mechanism for the oxidation of tertiary alcohols?

The oxidation of tertiary alcohols is generally more challenging compared to primary and secondary alcohols. This is because tertiary alcohols lack a hydrogen atom on the carbon bearing the hydroxyl group, which is typically required for oxidation. As a result, direct oxidation of tertiary alcohols often leads to cleavage of carbon-carbon bonds or requires harsh conditions and strong oxidizing agents.

Why are tertiary alcohols resistant to oxidation?

Tertiary alcohols are resistant to oxidation because the carbon atom bonded to the hydroxyl group does not have a hydrogen atom that can be removed during the oxidation process. The absence of this hydrogen makes it difficult to form a carbonyl group, which is a common intermediate in the oxidation of primary and secondary alcohols.

Can tertiary alcohols be oxidized to ketones or aldehydes?

No, tertiary alcohols cannot be oxidized to ketones or aldehydes directly. Instead, oxidation of tertiary alcohols usually leads to the breaking of carbon-carbon bonds, resulting in the formation of smaller molecules, or requires very strong oxidizing agents that can lead to complex mixtures of products.

What are some common oxidizing agents used for the oxidation of tertiary alcohols?

Common oxidizing agents for the oxidation of tertiary alcohols include strong reagents such as chromic acid (H2CrO4), potassium permanganate (KMnO4), and concentrated sulfuric acid (H2SO4). These agents are capable of breaking carbon-carbon bonds, leading to a variety of products including carboxylic acids, ketones, and carbon dioxide.

What are some practical applications of the oxidation of tertiary alcohols?

While direct oxidation of tertiary alcohols is not common in synthetic chemistry due to its complexity and harsh conditions, it can be used in specific industrial processes where breaking down complex molecules into simpler ones is desired. Additionally, understanding the oxidation behavior of tertiary alcohols is important in fields such as biochemistry and environmental science, where the degradation of organic compounds is studied.

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