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From a certain (admittedly narrow) perspective, one of the annoying features of natural language is the ubiquitous syntactic ambiguity. For a computational model intended to assign syntactic descriptions to natural language text, this seem like a design defect. In general, when context and lexical content are taken into account, such syntactic ambiguity can be resolved: sentences used in context show, for the most part, little ambiguity. But the grammar provides many alternative analyses, and gives little guidance about resolving the ambiguity.
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Hindle et al. (1990) studied this question.
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