Why i cant play a song downloaded from Youtube on Ipod Touch 4

Hi
I have couple songs download from Youtube from my laptop. Then i converted them to MP3 and transferred them to Itunes 10. I believed they worked well on the Itunes. but when they were transferred to my Ipod 4, i could not play them at all. Can you give me some advice how can i fix it ??
Thanks

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Hello,
I have exactly the same problem. It`s so annoying.
I did a little bit research on this discussion board and this problem seems to be known for quite a long time. It`s confusing me Apple is not able to fix that prob or give customers quick introduction to resolve the prob.
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http://support.apple.com/kb/TS1389
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I can play every song on the album but 2.
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Why i cant play a song downloaded from Youtube on Ipod Touch 4

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