How do I manually transfer music from my MAC to my iPod Nano (4th Generation)?

Recently, I have encountered a problem when trying to drag and drop songs and playlists from my Mac to my iPod Nano (4th Generation). I click on the file in my iTunes Library window but it won't allow me to copy it to my iPod. I've restarted both my Mac and my iPod but it hasn't helped. Do I need to download an update?Any suggestions would be greatly appreciated. Thanks.

Do I need to download an update?
Use Software Update to update iTunes if needed. Read the iTunes/iPod Summary page to find out if your iPod Nano needs any updates which you can download from there.
You cannot drag & drop anything to an iPod Nano. You must sync - Syncing Music to iPod

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We can get very detailed in how to complete this action but simply:
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Here are some possible solutions:
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Empty your "trash/recycle bin."
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how can i transfer music from my computer to my ipod?

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See:
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or
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How do I manually transfer music from my MAC to my iPod Nano (4th Generation)?

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