Sync problem with iPod Touch

I downloaded episode #1 of a tv show to my iTouch. Then I purchased the season of the same show, and downloaded it to my imac. This download included Episode #1 again. My iTunes folder correctly shows Episode #1 only once. However, when I sync my iTouch, I am not able to remove the original download of Episode #1 as it doesn't show as present on my imac.
What did I do wrong? How can I fix this?

Swipe your finger across the episode listing on your iPod and press the red delete button.

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