Restored iPod Classic won't download some songs purchased on iTunes

OK, so I just restored my iPod Classic so it could receive software updates through my new Mac Book. But now a few songs that I purchased from iTunes (all more than a year ago) will not upload to my iPod Classic. Songs that I purchased from iTunes during the past few months appear to have uploaded without a problem.

That didn't help directly, but you got me to sign on to iTunes and, to make a long story short, discover that I actually have two iTunes accounts. I think I signed up for the second one mistakenly when I activated my iPhone. All the songs that wouldn't play, were purchased under the account that wasn't yet authorized on this computer.
So now I have a new question for you. Is there any way for me to merge the two iTunes accounts?

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