Well giving Sasuke the Eternal Mangekyo Sharingan already kill half the people on the list. It is just like giving someone a handgun vs 10 barehanded guys.
Amaterasu will shut Hidans mouth but before that no Amatersu remember that, although Hidan is quite weak Sasuke will only be able to shut Hidan's loud mouth.
Itachi n Sasuke match it was clearly Itachi the victor.
Orochimaru n Sasuke match Orochi was shedding n Sasuke knew Orochimaru too well.
Deidara n Sasuke match if Sasuke didn't hide in Orochi snake he's a goner
That means Madara didnt kill Tobi, Madara dies from sickness causing Tobi to obtain MS and hate toward konoha. Even better Madara was trying to protect Tobi whilst dying in the process causing Tobi to hate konoha being the little brother. At the moment of Madaras death he gave Tobi his powers...
Itachi has clearly shown that can give mangekyo sharingan n more crap just by slapping people in the forehead(sasuke) n shoveling crap inside people. Mouth (Naruto) without killing