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I am very familiar with the expressions in column A below. How do these differ in meaning from the corresponding expressions in column B?
A B
Il aurait dû le faire il devrait l’avoir fait
Il aurait pu le faire il pourrait l’avoir fait
Il aurait voulu le faire il voudrait l’avoir fait
To me, the B expressions appear to be softened forms of: il doit l’avoir fait, il peut l’avoir fait, and il veut l’avoir fait, all of which bring to mind a courtroom situation in which one is awaiting the outcome of a trial: he must have done it, he may have done it, and he wants to have done it (assuming he can’t remember whether he did it or not).
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To help you understand common interpretations of the (B) versions, imagine saying in English:
"It ought to be the case that he did it"
"It could be the case that he did it"
"He wishes it was the case that he had done it"
In reality, both (A) and (B) may end up being translated similarly, since e.g. saying in English "He ought to have done it" can be interpreted as either "At that moment, it was necessary for him to do it" or "It ought to be the case now that he has done it".
(You'll also get some other possible interpretations of these forms, because the conditional occurs as a future-in-the-past in reported speech. But I'll leave that complication aside for now.)
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