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There is a Wikipedia article with the following line:

Drake sailed to the New World and sacked the ports of Santo Domingo and Cartagena in present-day Colombia.

Never mind the facts as we might know them; does the second part mean that Santo Domingo was sacked along with Cartagena, which is in present-day Columbia, or does it mean that both Santo Domingo and Cartagena are in present-day Columbia?

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A purist might expect that "ports of Santo Domingo and Cartagena in present-day Colombia" implies that both are in Colombia, and with an extra comma, "ports of Santo Domingo, and Cartagena in present-day Colombia" to mean only Cartagena was in Colombia.

I for myself would try to avoid this sentence structure altogether, if I could foresee such an ambiguity. I would either say "ports of Santo Domingo and Cartagena, which are in present-day Colombia" or "port of Santo Domingo and the port of Cartagena, which is in present-day Colombia." Well, that may be going a bit too far, though.

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It could mean either. The context might make it clearer, but it's a lesson to us all on the need for careful drafting.

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English grammar allows both interpretations, that is, the syntax does not restrict the semantics to one or the other. But, pragmatically, in this situation, it would be weird to talk only about Cartagena being in Columbia but not Santo Domingo., otherwise you would probably say something different to make it explicit that only Cartagena is in present day Columbia.

To answer literally, from phpSyntaxTree, here are two the parse trees:

[NP [ART the] [N ports] [PP [PREP of] [CONJP [N Santo Domingo] [CONJ and] [NP [N Cartagena] [PP [PREP in] [NP [ADJ present-day] [N Colombia]]]]]]]

enter image description here


[NP [ART the] [N ports] [PP [PREP of] [CONJP [N Santo Domingo] [CONJ and] [NP [N Cartagena]]]] [PP [PREP in] [NP [ADJ present-day] [N Colombia]]]]

enter image description here

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Another example of the dire need for proper punctuation, as identified by the Blessed Lynne Truss. The writer should have said "Santa Domingo, and Cartagena in present-day Colombia" (if he actually knew the facts), or "Santa Domingo and Cartagena, in ..." if he was staking the Colombian claim to Santo Domingo. Omitting the comma means that, by default, it is the second.

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