Sir John Tenniel's illustration of the Caterpillar for Lewis Carroll's Alice's Adventures in Wonderland is noted for its ambiguous central figure, whose head can be viewed as being a human male's face with a pointed nose and pointy chin or being the head end of an actual caterpillar, with the first two right "true" legs visible.[1]
The lexical ambiguity of a word or phrase pertains to its having more than one meaning in the language to which the word belongs. "Meaning" here refers to whatever should be captured by a good dictionary. For instance, the word "bank" has several distinct lexical definitions, including "financial institution" and "edge of a river". Another example is as in "apothecary". One could say "I bought herbs from the apothecary". This could mean one actually spoke to the apothecary (pharmacist) or went to the apothecary (pharmacy).
Syntactic ambiguity arises when a sentence can have two (or more) different meanings because of the structure of the sentence—its syntax. This is often due to a modifying expression, such as a prepositional phrase, the application of which is unclear. "He ate the cookies on the couch", for example, could mean that he ate those cookies that were on the couch (as opposed to those that were on the table), or it could mean that he was sitting on the couch when he ate the cookies.
There have been several posts on the theme of ambiguity:
Jay Doubleyou: how english sounds to non-english speakers
Jay Doubleyou: how english sounds to non-english speakers: part two
Jay Doubleyou: ambiguity
Jay Doubleyou: why is english so different from other languages? part one: vocab
Jay Doubleyou: why is english so different from other languages? part two: grammar
Jay Doubleyou: steven pinker - and language
Jay Doubleyou: ambiguous newspaper headlines
Jay Doubleyou: more ambiguity for the classroom
A couple of other things:
Ambiguities > Garden Path Sentences
The Greatest Enemy of Privacy Is Ambiguity
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