It would surprise me if there wasn't already an AI that could handle that class of question. Or, at least, I'd imagine it being relatively straightforward (non-trivial, but straightforward) to develop an AI that could handle it.
If someone has solved this particular type of problem (Winograd Schema), I'd be keen to know.
https://www.cs.nyu.edu/davise/papers/WS.html
https://en.wikipedia.org/wiki/Winograd_Schema_Challenge
http://commonsensereasoning.org/problem_page.html
http://spectrum.ieee.org/automaton/robotics/artificial-intel...
it refers to a breakable object made of either glass or iron. the ai then scans usages of the word shatter to see if it more commonly is used to describe glass or iron.
i searched google. "shatter iron" returns 500,000 results. "shatter glass" returns 2 million. 4/5 chance it refers to the item made of glass. in quotes the phrases return 4,640/186,000.
Wikipedia has another example (the original Winograd Schema) that doesn't allow you to "solve" the problem by asking Google:
The city councilmen refused the demonstrators a permit because they feared violence.
The city councilmen refused the demonstrators a permit because they advocated violence.
To what does "they" refer in each sentence?