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How does one describe the possessives of multiple parties? For example the apples of Mark and the oranges of Fred.

Would it be:

Mark and Fred's apples and oranges

Or perhaps:

Mark's and Fred's apples and oranges

Would it be different if one were describing the apples of Mark and the apples of Fred?

Note: I am looking for a sentence of this structure in particular; not a rephrasing which avoids the problem.

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It depends whether the nouns are acting separately or together.

  1. Use "Mark's and Fred's apples and oranges .. " if each of them owns these fruits.

  2. Use "Mark and Fred's apples and oranges .." if they share ownership of the fruits.

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