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It seems like I have the most trouble with ambiguous pronouns. I wrongly assume that a pronoun is ambiguous very often. Consider these three examples:

The city of Conway, Wales, now surrounds the medieval walls and castle that originally enclosed and protected (it).

True chalcedony is different from blue agate in the purity of its pale-blue color and, of the two, (is) the gemstone preferred by jewelry makers.

The essayist writing on art in America was less concerned with why funding was decreasing than with whether (it) was becoming less popular with the public.

Apparently, there is no ambiguity in the first two examples, but the "it" in the third example is, in fact, ambiguous. Why is this so? Is there a simple way I can identify whether or not a pronoun is ambiguous?

I have put the words that I think are ambiguous within parentheses.

In the second example, I thought that the "is" should have been replaced with "chalcedony is."

  • The answer to your question is No. – Colin Fine Feb 21 '16 at 0:36
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    The short answer is that you have to use encyclopedic knowledge to find the interpretation that makes the most sense, which is why this form of ambiguity is used in the Winograd Schema to test AI. – Roaring Fish Feb 21 '16 at 3:00
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There are two grammatical clues that help identify the antecedent -- gender and number. When those don't narrow the field to one candidate, you have to rely on semantics. Alas, grammar can take you only so far. Let's look at your examples:

  1. The city of Conway, Wales, now surrounds the medieval walls and castle that originally enclosed and protected it.

Gender doesn't help here as no persons are mentioned, but the pronoun is singular, so number eliminates walls. That leaves you with the city and the castle, but castle doesn't make sense: the castle wan't there to protect itself. It was there to protect the city. Now we can see that the author meant

The city of Conway, Wales now surrounds the medieval walls that originally enclosed the city and also surrounds the castle that originally protected the city.

  1. True chalcedony is different from blue agate in the purity of its pale-blue color and, of the two, (it is) the gemstone preferred by jewelry makers.

Neither number nor gender helps here. We have four singular common nouns to match the third person singular it. We can eliminate purity and color, since they're not gemstones. So which is it, true chalcedony or blue agate? The sentence doesn't actually say which stone has the higher purity of color; all it says is that the two stones differ. We have to infer from the adjective true that chalcedony differs in a better way from agate. And, indeed, chalcedony is the more valuable gemstone.

  1. The essayist writing on art in America was less concerned with why funding was decreasing than with whether it was becoming less popular with the public.

On gender grounds alone we can eliminate essayist as the antecedent. On semantic grounds, we can eliminate America. So what is the writer's greater concern -- the popularity of art or the popularity of public funding of art? Here you have an ambiguity not resolvable from the words. We might make a reasonable inference from the structure of the sentence that the essayist meant to stay parallel: "why funding was decreasing" balanced with "whether funding was less popular", but it's not dispositive.

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First, "is" is not a pronoun.

Your first and third sentences will sound awkward if the words in parenthesis are omitted. I wouldn't say they would sound ambiguous. Rather, they would sound incomplete or grammatically wrong. In your second sentence, you can omit "is" without any change in meaning.

If you repeat "the antecedents", as you put it, the sentences will sound redundant, not ambiguous.

  • I did not mean to suggest that the words in the parentheses should be removed. Rather, I was wondering whether the words in the parentheses should be replaced with their respective antecedents. – Grammar983 Feb 21 '16 at 0:16
  • "ambiguity", to me, means that a word or phrase can be understood in two or more senses – Centaurus Feb 21 '16 at 0:16
  • The third example, if I am not mistaken, is a question from the SAT . According to the test, the "it" can refer to either the "funding" or the "art." – Grammar983 Feb 21 '16 at 0:18
  • This is an (unofficial) explanation I found online: prntscr.com/a5xopg – Grammar983 Feb 21 '16 at 0:20
  • "funding becoming less popular with the public" ? I don't think it makes sense. Funding is or isn't popular with artists, not the public. – Centaurus Feb 21 '16 at 0:25

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