Actually there are roads connecting Alaska and Canada; the main Alaska Highway route runs from NE British Columbia up through the Yukon into the Alaskan interior and then turns SW towards Anchorage. You wouldn't be able to drive from Alaska to Russia, though. They're separated by the Bering Strait, which is about 50 miles across. You'd have to charter a private boat or plane to take you across the water to Vladivostok (there are no direct commercial boats or flights between Vladivostok and Alaska, in either direction; a lot of people choose to fly to Japan and then take a ferry across). And then once you're in Russia, you're looking at a very long trip across Siberia. There is only one road that connects Vladivostok to European Russia, which is about a 6,000 mile drive (or the equivalent of driving from New York to LA and then turning around and driving back to NY again), and apparently even that road isn't paved in some places, so that you need to budget at least a month to make the drive (there's a reason why most people who need to go across opt for the Trans-Siberian railway!).

So the most basic answer to your question is, a road trip from Canada to Morocco can certainly be done, but it's not nearly as simple as packing your suitcase and hopping in the car. You'd need to do a lot of research and preparation, planning your route and making arrangements in advance where necessary, and you'd definitely need a car that's rugged enough to survive the trip! And then if you're working you'd also need permission to take two or three months off. But hey, if you want to go and you think you can put it all together, then I say go for it! I think it would be a really cool trip!