How do i set the alarm on my ipod classic 6th gen to play a song at random from the library?

All you need to do is create a Smart Playlist, with a Media Kind of Music and Sync that Playlist to your iPod.

You choose from drop-down menus, it will take just a few seconds to create and rename.

This simple Playlist will contain every song in the Music Library, except songs that have had the tick removed. I use Sync only ticked songs and videos, so songs that are no longer ticked are removed from my iPod but kept in my Library. They are also excluded from this Playlist, thereby helping to keep the list tidy.

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On the iPod Classic - well on my iPod Classic, which I believe is 6th generation -

Look on your Main Menu. If Extras, or Alarms is not shown, go into the Settings/Main Menu and tick either Extras or Alarms - your choice. I'm using the Main Menu/Extras Menu.

From the Main Menu;

1. go to Extra/Alarms>Create Alarm
2. Alarm / On should be set as default. If not, I'm sure you know what to do!
3. Use the sub-menu list here to set the date and time for your alarm. After you have set each option use the Menu button to go back to the previous menu. (I noticed that the date menu uses the American date format even though I'm in the UK!)
4. From this same sub-menu, scroll down and go into the Sounds menu
5. In this option, you have to choose a Playlist. If you want a song totally at random, create a playlist that includes all your music. Otherwise, choose the Playlist you want to use.
6. Choose a messge that will be displayed, if you wish.

At the set time, there will be a short beep, followed by a song from your chosen Playlist. Oh! - and don't forget, the message will be displayed too.

One point I didn't test. I had my iPod set to shuffle songs. I guess that if I had this option set to no shuffle, the alarm may have chosen the first song in the Playlist.