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I am studying error analysis. why is the following sentence erroneous? *Last night I was very tired that I couldn't study. Is there an error in this sentence? The only option I can think of is Wrong use of quantifiers, but 'very' is not a quantifier it is an intensifier. What is the correct form of sentence? Should I replace 'very' with 'so'? Thank you

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The reason is that the rules of (that dialect of English) do not generate that output. There can be many ways of fixing the sentence, some involving big changes and some involving small changes. In order to know that the sentence is ungrammatical, you have to know the rules of the grammar, and determine if there is any path in the grammar that generates this output.

The problem is that you probably don't explicitly know the rules of the grammar. That is in part because "rules of grammar" are hypotheses generated by linguists to explain speaker behavior, and linguists change their minds on a weekly basis (there is no scientific consensus as to what the exact rules are).

Another approach, the one that most people rely on, is to use "acceptability" as a substitute for "grammaticality", so if native speakers do not accept a particular sentence, it is often said that the sentence is therefore "ungrammatical". This is not an entirely worthless approach, but it is fallible: sometimes the reason for a judgment of unacceptability comes from a non-syntactic cause (such as, using the wrong intonation).

An explanation that is not too closely tied to this week's Minimalism version 3.2.06 focuses on when you can use bare "that" – the problem is the complementizer. As a simple first approximation, "That+S" can be used when a sentence is a subject in a sentence ("That Fritz is wise is well-known" or extraposed "It is well-known that Fritz is wise") or object ("I propose that we eat the cake"), so there just is no syntactic slot for a That-S clause. However, there are constructions that would allow you to insert "That-S" into other kinds of clauses, for example "so that S", "to the point that S", "with the result that S".

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    Probly meant to be I was so tired that I couldn't study. Since so is often used as an intensifier, it may seem normal to substitute very for it. But there's a construction involved: so ... that S.
    – jlawler
    Commented Jan 7, 2022 at 0:02

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