My recently downloaded CDs to ITunes appear in my IPod Touch as light grey and a dotted circle on the left column of list of songs. and i have been unable to sync to my IPod. any idea why and what to try?

Downloaded songs into Itunes are not syncing to IPOd Touch though they appear in light grey and dotted circle in column on the left of list. Why?How sync?

what does the dotted circle mean?
What does the gray dotted circle in iTunes mean?
Dotted circles next to songs, won't sync, red circle with square?

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