"Since he was so familiar with the power of Web 2.0 tools and was surrounded by people who felt the same, he hadn't realized how many college students didn't actually have experience using these types of 21st century tools." (context)
Tough spot to be in. That's what you get for making broad assumptions about your students. Don't treat them like they're all plugged in 24x7, reading The Onion (or Wired), and waiting on the next tweet, twitter, ditter, or doodle. Good instruction starts with knowing who your students are and what they individually bring to the table. Don't think that they'll find it (or you) cool or hip just because it has to do with web-based technology.