The Web started as a tool for rendering text and occasional images pretty much as soon as it comes out of the wire. TeX on the other hand, was meant to be a typesetting package which compiles textual description of the document into a beautiful printable form. That compilation takes noticeable time even today, I imagine it was unacceptably slow for the web back before. Also in TeX you deal with paper sizes, in browsers you deal with adjustable viewports of unpredictable size.
I guess that the Web just started simple and evolved from that, and then nobody bothered to remake it for prettier text.
I remember an old publishing package, Ventura Publisher; the first time I saw it was 1990 or 91 maybe and then it was at v3. It was a very versatile publishing tool (all the perks of a professional typesetting package, tables, equations, floating illustrations; lots).
What's interesting is that it could separate the content and the styling information, so you could load the same content into two or more publications with different styles and get two different typesetting from the same source (e.g. one column small page for a book and two or three column large page for an article in a journal). And it was very easy to change the format or paper size: just change it and it would reflow the content accordingly. It didn't even took much time, as far as I can remember, and I'm talking about IBM PC 286 here.
So, truly, it's not a technical obstacle; web could have a much better typesetting engine working at high speed (and I'd say that it would be much better to imitate paged media instead of scrolling; scrolling is really inconvenient for reading). It's just that it grows wildly and in all directions at once; it tries to be a "semantic" storage, a rendering medium, and an application engine at the same time, and is not particularly good at any of this.
I guess that the Web just started simple and evolved from that, and then nobody bothered to remake it for prettier text.