Indeed it does, whats's the reason for putting them all on disc, if it's to deauthorise the PC to set up a new iTunes account on another computer you can put all your iTunes purchases on one compressed disc (won't play on a music system) to transfer to new PC, if it's just to get them on CD you'll have to use as many discs as it takes. iTunes will tell you if a disc is big enough for a playlist so it's easy enough to knock songs off.