Problems w new MacBook Air syncing itunes w iPhone??

I have a brand new MBAir and trying to sync some new music that was not bought on iTunes. (Bought on gumroad.com) Not sure if this is causing my issue.
The song downloaded fine to my computer straight into iTunes. It plays perfectly well on computer, but will not sync to my iPhone.
Why is this happening??!!!
Also, not sure if this is related, but I also keep getting the below message- even though I have authorized the new computer!
"This computer is no longer authorized to play purchaed items that are on the iPhone "my iPhone".
Would you like to authorize the computer for items purchased from the iTunes store?"
Help! I've authorized the MBAir repeatedly, but the same message keeps coming up.
Thanks to anyone who can help!

Hi loshi12,
If you are having issues with repeated prompts to authorize your MacBook Air, you may find the following article helpful:
Apple Support: iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
http://support.apple.com/kb/ts1389
Regards,
- Brenden

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Hello KM47,
It soundsl ike you are needing to copy your iTunes purchases to your computer rather than sync it at this point. You can use the following article to transfer your purchases with the following article:
iTunes Store: Transferring purchases from your iOS device or iPod to a computer
http://support.apple.com/kb/ht1848
If you have your library stored on another computer, you can also copy the library to the new MacBook Air with this article:
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http://support.apple.com/kb/ht4527
Thank you for using Apple Support Communities.
All the very best,
Sterling

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I have just bought a new MacBook Air.
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When you try to turn off the MacBook Air, do you see any message telling you that an app couldn't be closed? As a test, close all applications and turn off your Mac.
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If you had contacted Apple about each of the issues that you reported here, they would have kept a log of the problems that would help them determine whether to continue support after the warranty expires.
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Thats what often happens, seen it often. Youre in the 'dry' phase now.
next comes the corrosion phase Im afraid.
notebook is wet .....doesnt work...people get upset and depressed.
it gets dry (mostly).....works good or great.....people get happy and hopeful
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Hi gsantosoliver,
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Problems w new MacBook Air syncing itunes w iPhone??

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