i just got this chromebook acer c7, and i thought "hey no installing? poo on that" so now i'm running crouton (thats the technical term i believe), and its only my first day with messing about with all of this and the linux interface itself (i'm kinda proud i made it this far tbh). but anyways these log files should be sufficient with the sticky requirement post:
Do you get warnings about OpenGL when PlayOnLinux starts? This is usually critical for games, but some other kinds of applications can be affected too.
Warning: memory above 0x80000000 doesn't seem to be accessible. Wine requires a 3G/1G user/kernel memory split to work properly.
Don't know what kind of Linux kernel you're using, but it's not compatible with Wine.
[08/08/13 00:59:44] - The following file is located on a noexec mounted filesystem. It might prevent wine from working
The device you tried to run the iTunes installer from is mounted to prevent programs from running (for security), but it can prevent Wine from working correctly too. Change mounting options, or copy the installer to the internal harddrive first.