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You are on the right track for creating a properly tagged table of contents, but may not be using the optimal tool. You can use the Touch Up Reading Order (TORU) tool to tag pieces of the contents, then put them together in the right way in the Tags pane. Sometimes TORU does not offer the choice of the tag you need, for example a Reference tag. In that case you can tag the content temporarily as anything else then rename the tag in the Tags pane. If you want the chapter name, dot leader, and page number tagged individually just do so using the TORU. But that really is not necessary since all three go into the Link tag as one or more data elements, you can leave them together. You will often see examples where <Span> tags are used in cases like this to separate pieces of content within a tag, but doing so provides no advantage. Copious unnecessary use of <Span> tags merely clutters up the tag tree in my opinion. If your links are not yet created, I find it helpful to create bookmarks first then use the bookmarks to provide the page view for creating the link.
You will end up with something like this...
Link - OBJR
Chapter 1 ...... Page 1
Link - OBJR
Chapter 2 ...... Page 3
and so on.
One other thing, just a pet peeve of mine really. If the document will be available to the public I usually go to the trouble of artifacting-out the dot leaders since they provide no advantage for AT users, and will cause great annoyance for anyone using older versions of Adobe Read Out Loud - ROL will enunciate each and every "dot"! But tagging the leaders as background can be a bit time-consuming and few folks go to the trouble.
Hope this helps. Feel free to post follow-up questions. Accessibility really is the right thing to do. You are making the world a better place one document at a time.
a 'C' student
The easiest way to do this is to create them as linked items using styles in the source document (MsWord, Indesign, etc.). If you do this the tags should automatically appear in the desired structure. If you don't have the native files you are stuck doing it yourself.
An excellent resource on the preferred structure for Making Tables of Contents Accessible -- http://www.ehealth.va.gov/508/tutorials/pdf/8toc_1.asp
Using the Touch Up Reading Order Tool (TURO) works really well and C Student has some great tips. Another benefit of using the TURO is that you can probably draw a box around all the elements at once at tag them in one swoop.
But if you want to work in the Tags Panel to do it you can Create Tag from Selection using the Arrow/Blue Box tool that you mentioned in Acrobat XI (aka Edit Object Tool in the Print Production panel). Nor can you use Edit / Touch Up text tool in the Content panel. you have to use the Selection Tool which I find in the Navigation Toolbar at the top (not sure if it's there by default -- I think so -- but I've customized my toolbar.)
Thanks for your correct guidance. I was successful at creating a linked TOC in a PDF.