Googles intelligence when it comes to understanding URLs.

Selected answers from the Dumb SEO Questions Facebook & G+ community.

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  Philip Ellis: Hi guys, long time reader first time posting. I have a question regarding Googles intelligence when it comes to understanding URLs. I am about to engage in a lengthy content building campaign for a particular school test. I want to provide information for students about the NY Regents exam.
   ;I will have the domain: (website)dot com/regents
  In terms of keywords, I will be targeting /regents-prep and other 'regents' variatons. Rather than have regents occurring twice in the URL like this: website/regents/regents-prep, is Google smart enough to know that if I were to leave it as: website/regents/prep that I am targeting 'regents prep'. A mouthful there I know but I hope it all made sense.
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  Jim Munro: Hi +Philip Ellis ;, thank you for your participation here. :)
  
  I'm not sure if you meant to put regents(dot)com above but it goes to a real estate site.
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  Philip Ellis: My bad +Jim Munro ;edits made. ;
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  Jim Munro: Thanks, Philip. It's a good question, I'm looking forward to hearing our Panelist's answers.
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  Philip Ellis: thanks Jim, I know it was an mouthful but I hope it makes sense. ;
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  Philip Ellis: Brilliant thanks for the response guys.
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  Jim Munro: You are welcome, Philip, I hope we were able to be useful.