Can't authorize some songs after last update

After the last software update (most recent) I am getting an error that Itunes can't authorize 53 songs and one game for my computer to be played on my ipod. (3rd gen)
These songs were purchased on my powerbook. Some were even loaded off of a CD. I also can't figure out why the game peggle I bought can't authorize.
any thoughts?

iPhoto 9.6 only runs on Yosemite.
Option 1
Back Up and try rebuild the library: hold down the command and option (or alt) keys while launching iPhoto. Use the resulting dialogue to rebuild. Choose to Repair Database. If that doesn't help, then try again, this time using Rebuild Database.
If that fails:
Option 2
Download iPhoto Library Manager and use its rebuild function. (In early versions of Library Manager it's the File -> Rebuild command. In later versions it's under the Library menu.)
This will create an entirely new library. It will then copy (or try to) your photos and all the associated metadata and versions to this new Library, and arrange it as close as it can to what you had in the damaged Library. It does this based on information it finds in the iPhoto sharing mechanism - but that means that things not shared won't be there, so no slideshows, books or calendars, for instance - but it should get all your events, albums and keywords, faces and places back.
Because this process creates an entirely new library and leaves your old one untouched, it is non-destructive, and if you're not happy with the results you can simply return to your old one.  
Regards
TD

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    iPhoto 9.6 only runs on Yosemite.
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