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This study questions the developmental nature of the ability to understand syntactic structures. An exploration is made of the possibility of learning more about reading comprehension and readability by examining responses made to sentences described by transformational grammarians as structurally ambiguous. A group of fifth grade students were asked to identify paraphrases of three kinds of sentences, ones with ambiguous surface structure, ones with ambiguous underlying structure, and ones considered to be unambiguous. (An example of a sentence with ambiguous surface structure is, "Small boys and girls are easily frightened." An example of a sentence with ambiguous underlying structure is, "Flying planes may be dangerous.") Although the fifth graders did not do well on the test, the order of difficulty of items was found to be similar to that found by other researchers. The order of difficulty ranged from unambiguous sentences as easiest, to surface structure ambiguities as next in difficulty, and underlying structural ambiguities as most difficult. Oral interviews with eight of the students after they took the test resulted in improved scores. A comparable study by Montague is reviewed and similarities in research findings are noted. (MKM)