My iPad air won't sync with my music in iTunes on my MacBook Pro

I have tried to sync my new iPad air music through iTunes with the music on my MacBook Pro using a direct cable.
A message box opens and says that this computer is no longer authorized for purchased items on this iPad. Select Store and authorize.
I go to store and authorize this computer with my AppleID and then a box opens and says the this computer is already authorized?
It just keeps going around in this circle.
Any ideas.
Thanks!

Seriously?  There are various reasons why I don't use the Cloud, but I want to sync my calendars on my iPhone with my new MacBook Pro.  So I've been setting up the new machine, and most things work, but I can't get the phone to sync calendars with the MacBook.  The instructions (on the laptop) say to plug in the phone, and go to iTunes, select the device (the iPhone) and then click the Info tab.  But there is no Info tab to click.  I've searched and searched, and cannot find it.  So, now I'm thinking, is this the answer to this problem that Apple hasn't alerted me to?  ...or am I a complete moron for not being able to find it?  The look in iTunes is different from what I'm used to looking at in my old machine (an older MacBook). 
Music, iTunes U, and other things seem to sync properly.  I haven't investigated yet to see whether my calendar is syncing up right.   
I don't keep up on all the nomenclature:  "Mavericks" refers to the new OS that came with my Macbook (10.9.1)? 

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