HT1351 playlist on mac is not the same on nano after sync any tips?

I have an updated play list on my mac that I want to show on my nano. When I sync the songs do not display in the same order on my nano and some songs are missing. They are all checked on my playlist in itunes on my mac.
This has never happened before - usually worked like a charm - any tips?

Hi
I have checked Sync Music and also entire music library. It is weird because this has always worked before.
What I create are playlists for running. Every 10 minutes I insert a one minute short song for a walk break. On my mac, I set it up in the playing order I want, sync and off I go.
Yesterday I took an existing playlist and just added a couple of songs to lengthen it as I am doing a long run Sunday. Thats when things went wrong!
The play list on my mac is perfect. The one on my IPOD put all the one minute songs together in a row so it didnt hold the format.
Help appreciated - this is my first 1/2 marathon and I need my tunes!
Thanks

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