Songs purchased from iTunes not syncing

In the last week I have purchased 3 songs from the iTunes store using my iPhone. Whilst these songs do show up on both the phone and on my iTunes itself, whenever I play them on the iPhone and then sync the phone it doesn't register that I've listened to them recently. Also, I havre added them to a custom made playlist on several occasions, and then when i sync my phone they disappear from the playlist and I have to put them back every time. I have tried adding them to this playlist using both the iPhone and iTunes, but it doesn't seem to make a difference. I have a playlist on iTunes of songs I have purchased, and these 3 songs do not appear in the list.
Can anyone tell me why this may be and if there is any way I can fix it?
Many thanks

thanks

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I need some everytime I try to download a song purchase from itunes I get the error message. 'Unable to Download Song' could not be downloaded at this time. I cannot even sync with itunes on the PC.
Kind regards
Ian

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