ITunes not syncing more than 1 song at a time with SLVR

I need some help with Itunes and syncing it to my son's Motorola SLVR L7. It seems that if I try to sync more than 1 song at a time, it fails out saying that it can not find file. I can sync one song at a time, but I have to disconnect and reconnect the phone each time. It would take forever to do 100 songs. Does anyone know how to fix this issue?
I also have 2 iphones, v1 and have not problems with them.
Thanks for the help.
Ron

Yes.  Click the first track, and hold CTRL while you click additional tracks.  Then hit Delete.
(If the tracks you want to highlight are in a row, click the first, hold Shift and click the last.)

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