Why translating language to propositional logic is tough?

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Translating natural language into propositional logic is challenging due to the complexities of context and inference inherent in everyday language. Natural language often contains vague expressions and unsaid information that are easily understood by speakers but difficult to formalize. Formal logic requires precise definitions and mutual agreement on meanings, which can be burdensome when translating. Additionally, natural language conveys more than just logical statements, as words can carry various interpretations beyond strict truth values. This complexity makes the conversion process from natural language to propositional logic a nuanced and demanding task.
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Why is it so hard to convert natural language to propositional logic. We are so comfortable in understanding and interpreting english or any other language we know.
But when we need to convert it into something formal, we have to think. It does not come that naturally. Why?

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Well, interpreting natural language sentences involves a truly ridiculous amount of inference based on context. We also say a lot of really vague things which get an immediate point across, but don't have a very well defined meaning if you dig even a little bit into it. On the other hand formal logic in some sense assumes that whatever proposition you are using, everybody should agree on what it means, down to the last nuance. This is really quite a tough burden to meet.

We leave a lot unsaid in most sentences, but to be formal you have to put all that information back in.
 
Usually translating natural language to propositional logic lacks the context that surrounds natural language. So you must include enough in the logic to make explicit what a hearer of natural language infers from context. For example "There's a psych major in every dormitory" isn't interpreted to mean that there is a single psych major who has a room in each dormitory.

Also, natural language doesn't exclusively communicate logical statements. (For example, to the man-in-the-street, the word "logical" may mean "true" or"plausible" or "probable" or "appropriate".)
 
The standard _A " operator" maps a Null Hypothesis Ho into a decision set { Do not reject:=1 and reject :=0}. In this sense ( HA)_A , makes no sense. Since H0, HA aren't exhaustive, can we find an alternative operator, _A' , so that ( H_A)_A' makes sense? Isn't Pearson Neyman related to this? Hope I'm making sense. Edit: I was motivated by a superficial similarity of the idea with double transposition of matrices M, with ## (M^{T})^{T}=M##, and just wanted to see if it made sense to talk...

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