It hasn’t even been officially announced yet, but Google’s rumored purchase of Groupon for $5-6 billion is already coming under fire from observers. This may be Google’s biggest purchase ever (DoubleClick, the runner up, sold for $3.1 billion), but that in itself is raising questions. Google’s other major purchase was YouTube for $1.76 billion, and that has yet to turn a profit.

Then there is the Facebook question. Today, Facebook is the only website that can potentially challenge Google’s rule of the roost. And the two have less than friendly relations. Facebook is hesitant to share information with Google, but one of Groupon’s big appeals is having users share deals with friends using Facebook Connect.

Then there is the new Facebook Deals, which could rival Groupon as the platform for discount mass shopping. That coupled Facebook’s Places could let people share the best local deals with their closest (proximity-wise) friends using little more than a smartphone. Groupon may be the newest “big thing,” but if Facebook’s copycat Deals takes off, Google could be throwing its money away.

Then there is the anti-trust question. Google is already raising questions among federal investigators because of the enormous information it has about people’s buying habits. Google is already coming under fire for its proposed acquisition of ITA, the flight information software behemoth. Adding Groupon to the mix might just add enough fuel to the fire to get investigators very worried.
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