I have song in itunes that will not load onto ipod ?

I have a song in itunes that will not download onto ipod, nothing by song in library indicating there is a problem. Can anyone help me ?

Does the song have a tick-in-the-box next to the song title? (You may have selected to Sync only ticked songs and videos to your iPod. This option is on the Device/Sumary pane that appears when you connect the iPod to iTunes.)
Is the song in a format the iPod can play? (Is it the same format as other songs that do Sync to your iPod?)
Have you looked (on the iPod) under songs as well as artists? (It may show up under songs but not under artists.)
Try the Search facility on the iPod and see if it shows up that way.

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When songs cannot be found, it's either because they have been moved from the original location that you told iTunes, renamed or deleted.
So have you:
renamed songs?
moved them to a different loaction on your computer since you imported them into itunes?
deleted them since you imported them?
stored you iTunes library on an external drive? If so, that drive needs to be on and ready every time before you start iTunes.
... or is another programme renaming or even moving them, such as Windows Media Player? (It has been known to if you let it.) Did you previously use Windows Media Player?

I have songs that have been purchased and they show up in my I tunes but the are not showing up bold like all other songs in my library, they will not let me download from the cloud and will not load onto my ipod.

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Welcome to the Apple Community.
So far as I am aware, books haven't been available for 6 years, so I'm wondering if you mean audiobooks.
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Reinstalling Lion/Mountain Lion Without Erasing the Drive
Boot to the Recovery HD: Restart the computer and after the chime press and hold down the COMMAND and R keys until the menu screen appears. Alternatively, restart the computer and after the chime press and hold down the OPTION key until the boot manager screen appears. Select the Recovery HD and click on the downward pointing arrow button.
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OR
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2. Reinstall Snow Leopard
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Download and install the Combo Updater for the version you prefer from support.apple.com/downloads/.

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Sean
6023639400

Sounds pretty definitely broken.

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I have song in itunes that will not load onto ipod ?

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