Organic chemistry

[shefv]

Can someone explain this (maybe with a drawing)?

I understand that during oxidation, all the OH groups will become C=O, I thought there would be 3 ketones.

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[lifetothefullest]

Tertiary carbons don't oxidize. Return to the fundamentals: what happens to alcohols when they oxidize? The oxidizing agent removes a hydrogen from both the oxygen and the carbon to form a double bond. So primary and secondary alcohols can be oxidized because they have hydrogens attached to the carbon. Tertiary carbons don't.

 

[shefv]

I see that the one primary carbon attached to OH - that is where the one ketone group will form.

What about the carboxylic acid?

 

[lifetothefullest]

I see that the one primary carbon attached to OH - that is where the one ketone group will form.

No, full oxidation is happening. What happens even after the ketone forms on the primary carbon? Can another hydrogen leave so that it can be oxidized further?

Where does the ketone form (hint: not the primary carbon).

 

[NextStepTutor_1]

Under conditions that allow complete oxidation, ketones are derived from secondary alcohols and carboxylic acids are derived from primary alcohols.
Via oxidation:
Primary alcohol ---> Aldehyde ---> Carboxylic acid
Secondary alcohol ---> Ketone
Tertiary alcohol ---> nada, a tert alcohol cannot be oxidized
Quaternary alcohol ---> quat. alcohols do not exist