ITunes library files won't move to iPhone

I downloaded language lessons to my iTunes library. I cannot get the files onto my iPhone (with or without iTunes Match turned on). The files are only 80 kbps so will not go to the iCloud. I can drag the files just fine to my iPod Nano. Any suggesitons?

Run Repair Disk.
First check the S.M.A.R.T. status on your HD: Applications>Utilities>DiskUtility>in the panel at left, select the first item in the list/your HDmechanism>look at the bottom of the main window next to S.M.A.R.T. statusand see if it says “Verified” or something more ominous like “Failing.”
If S.M.A.R.T. status is "Verified," run Repair Disk:Boot from install disc (insert disc>restart>immediately hold down c keyand keep holding it until you see “Preparing Installation”)>at first screenselect the language and click Continue> click on the Utilities Menu in themenu bar>open Disk Utility>select your HD in the panel on the leftside>click Repair Disk at bottom of main window. Run this at least twice,and keep running it until it says “appears ok” twice in a row. If that doesn’thappen, you may need a stronger utility such as DiskWarrior orif the directory is damaged beyond repair, you may need to reinstall the OS, oryou may have a damaged HD (repair utilities can only repair the directorystructure, not the HD itself). When this is finished, quit Disk Utility, quitthe installer, and restart. Once booted normally, go toApplications>Utilities>Disk Utility and run Repair Permissions.

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