How do I transfer music between my devices?

I have music I have purchased on my iTunes on my Mac that is not on my iPod and I have some music on my iPod that is not on my Mac. But there are some of the same songs on each. Why did only some songs transfer and how can I get the songs missing from both my iPod and Mac on both of the devices? Thank you!

OPen itunes, connect device, select what you want to be on the iphone, sync.

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