Some iTunes music content is listed as having been synced to my iPhone, however, when I try to access it on my iPhone, it's not there. How can I fix this?

I had a problem that some of the content I had purchased from iTunes was skipped over when I tried to play it on my iPhone. Music copied from CDs and some other content from iTunes worked fine. To try and fix this, I removed all the music from my iPhone and then added it all back on again. This worked for some of the content that was being skipped over, but now some of the content that was being skipped over doesn't appear on my iPhone at all.
When I open iTunes on my MacBook Pro and choose "On This Phone", there are 100 songs - all purchased directly from iTunes - that are listed as being on my iPhone but aren't there when I open iTunes on my iPhone. I also notice that you can't redownload purchased tracks from the iTunes store.
Please help. Thanks.

Answers to the similar "No Content" question seem to say I should turn off ZoneAlarm. However, I can't find this option in iTunes and some Googling suggests that ZoneAlarm isn't actually an integral part of iTunes anyway so that doesn't seem to have helped.

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