English Translation
If I tell you a story, will you go to sleep?
I wonder if andare a dormire isn’t too literal a translation of “go to sleep” (fall asleep)?
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No, it is a very natural expression.
What is not very natural, is the use of the “Lei”, I expect this is something a parent says to their child.
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So is it a synonym for addormentarsi? Would this work: “Sono andato a letto ma non sono riuscito ad andare a dormire” (I went to bed but couldn’t go to sleep)?
I won’t be able to go to sleep tonight unless I get this straight 
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Not really. “Andare a dormire” means “to go to bed (for example) with the intention to sleep, preparing for sleep”.
“Addormentarsi” means “to start sleeping (for real)”. It is something that happens after you go to bed (in the optimal case; “addormentarsi alla guida” would be quite bad).
So your example does not really work in Italian.
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