I always thought it odd that Tsunade chose to send a group of genin lead by a fresh chunin after Sasuke. Could they really have been that hard up for shinobi? What if they didnt send naturo but instead, I dunno Kakashi. Yeah he was away while everything went down and didnt arrive back in village well after everything had started, but what if he was around? If Kakashi had been sent after Sasuke, do you think it would have made a difference? Would he have been able to get the job done?
Think first. Sasuke was placed in that cylinder fairly early into the story. Once he was in I doubt he could have been taken out without killing him in the process. Even if Kakashi would have been able to defeat all of Orochimaru's shinobi do you think it would have made a difference to bring back an already altered Sasuke? It's obvious his time in the cylinder effected him mentally as well as physically. At the level Naruto and Sasuke were fighting at toward the climax of the fight, do you think Kakashi would have been able to beat Sasuke? Well, what do you think?