Itunes says it synced but nothing plays on shuffle

I just got a new shuffle for my husband and tried to load the music he wanted.  iTunes says it's synced, but when I plug in the headphones, the voice says to use iTunes to load music.  So apparently, iTunes didn't sync.  I've plugged it back in to the iMac and tried again (twice), but it just says it's synced and can be disconnected.  In iTunes, if I click on "on this ipod", it shows everything I want on it.  Still no music playing, however. 

Hi pic-chic,
Welcome to the Apple Support Communities!
I understand that you want to sync music to your iPod shuffle. After you click on your iPod in iTunes and then click on the Music pane and select the music you want on your device, make sure to select Apply in the bottom right hand corner. Please use the following article as a reference.
iTunes: Syncing media content to iPod
http://support.apple.com/kb/HT1351
Syncing music
Connect your iPod to your computer and open iTunes.
Click the button with your device's name, below the Spotlight window.                                              
In the main iTunes browser window, select Music.
Select Sync Music. You can select "Include music videos" if you want to sync Music videos to your device.
Your device needs to have enough free space to sync the content that you selected from your library.
Tip: You can use the capacity bar at the bottom of the device settings window to see how much free space is available. The window will update with an estimate as you select content.                  
Click Apply. iTunes will sync the content you selected to your device. The iTunes LCD will show the sync progress and notify you when the sync is complete.
To disconnect your device, find your device in iTunes and click the eject icon.
Have a great day,
Joe

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