iPhone won't sync all music?

I plugged my iPhone into my laptop with an old iTunes library to charge and when I later unplugged it and went to listen to music, a lot of it was missing. I went to re-sync my iPhone with my desktop with the updated iTunes library and all of my music, but when I hit sync it says " Step 1 of 2 Determining which songs to sync" and then immediately finishes. I checked the sync entire music library box but it still will only put 268 of my 361 songs on my phone. I tried restoring it and when it began syncing music it said syncing song 1 of 268. WHY WON'T MY OTHER 93 SONGS SYNC!!!??
 
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