Unable to sync certain songs?, unable to sync certain songs?

Hi im new to this & not very computer savy. i loaded itunes cloud a few months ago. then stopped it half way through ,as it had taken 4.5 hrs already and ever since then i have lost (greyed out) many of my songs and i am unable to load them onto my phone even tho the play on my mac ??????? can anyone help please?

What format are the songs that won't move? Some formats that play in iTunes are not compatible with the 1st generation iPod shuffle, Aiff and Apple Lossless for instance. Apple Lossless is not supported on the 2nd generation shuffle:
iPod shuffle: Compatible audio formats
iPod shuffle 2nd generation - Technical specs
Some songs in iTunes won't copy to iPod

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