Question

When oxidizing a secondary alcohol, only one product is formed. What is this product? Why is it that in our reaction a different product was formed?

Why is it not possible to oxidize a tertiary alcohol?

Answer 1

Whenever you try to oxidize a secondary alcohol, you will get the same type of product. In this case a ketone. as you can see in the following mechanism (As example, cause I don't know what's your product)

Now, as you may see in the last steps of the mechanism, in order to produce a ketone, it's neccesary that the carbon loses it's hydrogen to finally form the ketone.

In a tertiary alcohol there are no hydrogens atoms to lose in this step to form the ketone, cause all the bonds of the carbons are bonded to another molecule (a chain, another radical) and these are bad leaving groups, so, it does not happen anything with this kind of alcohols.

Now, for your second question, it's possible that your alcohol is tertiary and therefore, you didn't get the ketone, of maybe it's a primary alcohol and you form a aldehyde instead of ketone.

Hope this helps