Symptom
AIFF files you copied from an audio CD in the Finder don't play on the iPod, but they play OK in iTunes.
Solution
When you copy an audio track from an audio CD using the Finder, the result is an AIFF file that iPod cannot play. However, iPod can play the audio tracks if you import them as AIFF file in iTunes instead. For instructions, see technical document 93118, "
iTunes 4: How to Choose Import Options."
Important: iTunes software may be used to reproduce materials. It is licensed to you only for reproduction of non-copyrighted materials, materials in which you own the copyright, or materials you are authorized or legally permitted to reproduce. If you are uncertain about your right to copy any material you should contact your legal advisor.