I downloaded a song from i tunes onto my computer but it will not sync it into my phone

I just downloaded a song onto my computer from itunes and hooked my iphone up to sync it and that song will not appear anywhere on my phone.  I have tried rebooting my computer and my phone as well as redownloading the song but nothing seems to work.  What am i doing wrong?

Maybe the file type is not supported by itunes, what is the extension on the end of the song?

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