Question for any chemistry wizzes still around

[linotas]

Scenario as follows:

Senior Chem prac, properties of organic compounds. Tertiary and secondary alcohols brand new and unopened bottles. Tertiary alcohol looks the real deal (solidified at room temp - yes its cold here ) Tertiary alcohol oxidises with potassium permanganate, secondary alcohol doesn't.

Same things happened last year and we thought the chemicals had been contaminated so brought new ones in. Besides the manufacturers providing the wrong chemical, we are at a loss to explain it.

Any thoughts?

[JelJane]

Can you tell me what the formulas of the specific alchols you are trying to use are...?

Sounds odd...

[Graham Kemp]

No. That does not sound right at all.

Tertiary alcohols are supposed to be highly resistant to direct oxidation. Certainly secondary alcohols should be more easily oxidised.

What exactly are the names of the alcohols that you have?

[Graham Kemp]

To be clear: Tertiary alcohols can be oxidised by potassium permanganate (esp. in acidic conditions). It's a strong oxidizing agent, so that's not too unexpected.

The puzzler is that the secondary alcohol didn't oxidise at all when it should be more prone.