I'm not fully confident in my response but will give it a shot based on experience.
Also, please allow me to respond in English, because I can't explain this in easy Japanese.
As you know, "と" in the first example "ringo wo hitotsu to mikan wo futatsu" is simply nouns being conjoined with "to."
The second one is a question of a different nature, asking your preference. By adding two "と," the suggestion is "apple on one hand and mikan on the other."
So there is a difference of the first lumping apples and oranges together into one group and the second implying separation into groups.
Epigene nailed it of course. in the second sentence "to" is about equivalent to "of/between/and"
For example
Of Apples and mikan which do you like. There are many different ways to say this in english. I think "Which do you like between X and Y." maybe more commonly used.
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