Can't copy all songs from an imported CD

I have an OLD 15gb iPod. I bought a new CD and successfully imported all the songs into iTunes (V.7). I then selected all songs and dragged them to my iPod. However, only some of the songs copied. I cannot even drag some of them one-by-one to my iPod from iTunes.
I cannot figure out why I can't copy all the songs.
Any help would be appreciated.

I never laughed in all my life. Here I was, inserting the cd Dance with Me, thinking it's not going to copy the whole thing. yeah, right.
Sure, it prompted me, Do I want to replace the songs, so of course I said "no, don't replace the songs". and guess what it did. It copied the whole cd (at least I got my two songs).
I went into the itunes library, and sure enough, all the songs were there twice. So what did my intelligent brain think of? I just unchecked the doubled songs and stuck my ipod into my computer and it synched up and I got what I wanted.
Now what did I do wrong when it prompted me. I clicked on "don't replace" and it replaced them anyway.
Am I dumb? or is itunes stupid?
thanks, Melody

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I fixed this issue (with help from tech support) and it involved several things.
After adding a song to iTunes, right-click on the song in iTunes and select "Update iTunes Match."
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If you right mouse and select Get info it will show you the Apple ID used to purchase these songs.
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I can't copy certain songs from my iTunes library to my iPhone despite repeated attempts. These are songs I copied way back when from CDs onto my computer. I can play them on my computer just fine in iTunes too. Status bar says "Updating files" and "Preparing to Copy" but nothing actually copies to my phone. My phone shows the songs greyed out and circles to the left of the song in the Store column and the songs never get copied onto my phone.
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Message was edited by: dinosaur_bones_12345

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Can't copy all songs from an imported CD

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