Getting iTunes songs onto the iPhone

I have 40 songs on my Mac.  However, only 13 of them will download to my iPhone.  Why won't some songs download?

Wow, thank you for the fast reply.  I've had my Mac for about five years and just got my first iPhone.  That's an interesting question and sounds plausible.  When the Mac asks me to log in it prefills my email address, however, my Mac ID actually is something else but it's possible I bought some earlier iTunes under the name that's being prefilled.  What is odd is that the 13 songs that did download were purchased at many different times (some several years ago, some very recent...).
I first went into iTunes on the iPhone and downloaded one song.  When that worked, I asked it to download all and it downloaded 11.  I then clicked on "Not on This Phone" it says "All of your available music has been downloaded to the device."  I then tried Home Sharing but that didn't seem to do anything.  I then bought iMatch and it also didn't do anything.  I tried buying a new tune last night through the Mac and I think it downloaded automatically to the iPhone...I actually am not sure if it automatically downloaded because I so often pressed various things trying to get the iMatch to download all.

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