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I have very little exposure to machine learning so my question may not make sense.

Machine Learning is based on statics that does not have strict rules where as Grammar is a set of strict rules. Does it make sense to evaluate the strict rules using statics ?

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Yeah, it doesn't use strict rules, or rules at all, that's the cool thing. It looks for sections of text that don't "sound right." This is where the deep learning comes in. It learns over sequences of vectors, where the vectors represent the words in the sentence.

Grammar isn't a set of strict rules.

It is in the formal sense, and in a practical sense too (if you have an impractical amount of rules, anyway ;).

Strict rules doesn't necessarily mean the rules (productions) are context-free.

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