Don't think Naruto can ever beat a jounin alone (at least now) - not because he does not posses the chakra levels or powers as other jounins, but because he simply lacks the experiance in battle...
Other Jounins can anticipate what Naruto is going to do a mile away, while he will not see it coming until its too late.

From time to time he does manage to think of a cool trick (being the surprise ninja that he is) - and that may change the tide of the battle; but will never win him a 1 on 1 fight with a jounin imo.