Sync music from ipod shuffle on itunes to new iphone

I have over 300 songs that show up on my itunes account that I have purchased over the past many years. When I sync my iphone to my itunes account, only music that I have purchased since purchasing my ipad a couple years ago will download on my iphone.  How do I get my older music about 200 songs to download to my phone?

Hello khollyoak,
Thanks for using Apple Support Communities.
For more information on this, take a look at:
iTunes: Transferring media from your iPhone, iPad, iPod touch, or iPod
http://support.apple.com/kb/HT1209
Music purchased from the iTunes Store
Transfer your content via iTunes.
Download your content through iTunes in the Cloud1.
Download your content through iTunes Match2.
Music imported from a CD or another source
iTunes cannot transfer this media back to a computer. Make sure to back up your iTunes Library, or you can use iTunes Match2.
Best of luck,
Mario

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