I was able to put this to the test yesterday. Wandering around some of the course 6 listings, I happened upon 6.805, a class on computer ethics and law. One of the top student papers submitted was on information Google collects on users, a topic that I have a bit of familiarity with (and some opinions too!). Having context for the topic helped me; in fact, I anticipated some of the problems they had with their initial design.
Now when I was an undergrad, there was no web, but there were "services" (like ftp and telnet) that one provided personally identifiable information to (such as your login and password). There were also proxies that relayed this information from the Chaosnet network on campus to the ARPAnet and Internet (such as it was back then). So such a paper could have been assigned, subject to the technology of the day. I had much less context about such things than I do now, so I may not have had the level of understanding of such subjects. I remember at some times feeling the assigned readings were really dense; usually, the more familiar I was with the topic, the less dense the readings seemed. (An indication of how well I understood what I was reading was if I anticipated a problem with a design, and it turned out to be so.)
I recall having to critique readings on other aspects than technical. Ethics came up fairly often. There was one reading discussing a future society in which electronic payment was necessary for participation in most kinds of commerce. We were asked to comment on the ethics of such a scenario, particularly with respect to people from parts of the world where electronic funds transfer (EFT) was either expensive or not widely available. As it turns out, this is a problem for some AdSense publishers, because EFT is not available in all countries. Google will mail checks in the target country's currency, but some publishers have experienced checks getting lost or damaged in the mail.
Were I to teach such a class (unlikely), I might ask the students to discuss the ethics of anonymizing software. It's a touchy issue for search engines because of the privacy implications vis-à-vis the need to deliver relevant ads, provide auditable data in case of fraud, etc.