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>> Reminds me of a weird scene in Star Trek IV where the crew went back in time to 1986 San Francisco. Uhura and Chekov were asking people on the street and a cop where Alameda was. I say “weird” because both of them went to Starfleet Academy in San Francisco, so their not knowing where Alameda is is as bizarre as someone in Manhattan not knowing where Brooklyn or Queens is. <<

I don't find the scene bizarre, it makes sense given how far back in time they've traveled. Yes, Starfleet Academy is located in San Francisco, but they're from the San Francisco of 2286 -- 300 years into the future! The San Francisco of 1986 likely bears little resemblance to the San Francisco they know, aside from a few iconic landmarks scattered here and there like the Golden Gate Bridge.

Just imagine if someone who attended present-day Rockefeller University had to navigate around New York City of three centuries ago: c. 1716, long before Rockefeller University ever existed. The neighborhoods, community areas, and streets of that time period bore little resemblance to modern New York. They'd be entirely lost. And yes, they WOULDN'T know where Queens is, since the present-day boundaries of Queens was established in 1899 and it was entirely different back in 1716. Even going back to the civil war area, what is the present-day lower Manhattan commercial district and the former site of the World Trade Center was a seedy lower-class immigrant neighborhood called the "Five Points" filled with gang warfare (as seen in films like Gangs of New York).

>> Unless Alemeda gets wiped off the map at some point, annexed or renamed. <<

Given the events of Star Trek's future timeline (earth was devasted by a third world war in the mid-21st century that killed over 600 million people and wiped out most of the present-day major cities in the world -- with a handful of exceptions like London and San Francisco), I think that is likely what happened. It's probably not even called "Alemeda" anymore in the time period Chekov and Uhura are from, and may not even exist anymore. It certainly isn't used as a naval station in 23rd century, judging by their reactions. (incidentally, if you went BACK in time 300 years from the present-day, that would also be the case -- what is now Alemeda Island was originally a peninsula connected to present-day downtown Oakland, and it wasn't renamed Alemeda until 1853).