Songs not showing up on phone after syncing

I am trying to sync some songs onto my phone, and I have put them into a playlist, all of the songs are checked off and whenever I have tried to sync the songs onto my iPhone they don't show up, and whenever I go back to the playlist on my computer the playlist is blank I have no idea how to fix this

Try using Restore on the iPod shuffle's iTunes pane. If that does fix the problem, use the iPod Reset Utility, which is not the same as Restore in iTunes.
http://support.apple.com/kb/HT1238
some songs (usually one or two) either play a half-sec, or the song just isn't there...
Do a Get Info on those songs in iTunes to see if there is anything in common about the music files.

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