THE most successful cities achieve a kind of organized chaos — a rich, dense and varied mix of different kinds of people, ideas and businesses, constantly colliding in new and interesting ways.

Jane Jacobs, an urban activist, made that observation in 1961 in her landmark book, “The Death and Life of Great American Cities.” Although she was describing cities built of bricks and mortar, her ideas about cultivating vibrancy feel relevant today, as some of the most important metropolises of the 21st century are being constructed online, where chaos is in no short supply.

The latest controversy surrounds Reddit, a community and social news site that lets members create and run their own forums on any topic, from movie news to local politics to the sharing of beautiful nature photographs. Reddit has come under fire for harboring a forum that encourages people to covertly photograph women on the street and upload the images to the site for others to ogle and comment on. The pictures, nicknamed “creepshots,” incited outrage and provoked other members of the site and some journalists to publicly out those distributing the suggestive images. These actions, in turn, prompted an outcry from those who felt that they should be able to retain their own anonymity while posting photographs of women without their consent.

The skirmish has set off a debate about privacy and free speech, ownership and community, digital rights and accountability, touching upon issues of privilege and the undercurrents of power that course through the Web. At its core, the fallout is about how we transport social order, morals and responsibility to the digital realm and whether the online infrastructure can find a weird wisdom in the way it is being erected that will allow all its inhabitants to flourish.