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The first sentance is equivalent to : Et si il avait déjà quitté l'île, et que son bateau ait coulé quelque part au milieu de l'océan ? But it implies the speaker made an hypothesis and ended his sentence. Then, he thought of something else (something even worse!) and added it. The sentence is imperfect, but it shows the train of thought of the ...


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Your first sentence is implying a single possibility : he already left the island and his boat sunk in the ocean. Your second formulation would imply 2 exclusive possibilities using an enumeration of "Et si ... ?", which is kinda illogical and would sound weird. You would also use "avait" instead of "a" in the second formulation. Concerning the punctuation ...



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