Breakdown of Können Sie das Dokument kopieren, wenn der Chef es unterschreibt?
es
it
Sie
you (formal)
der Chef
the boss (male)
können
can / to be able to
das Dokument
the document
wenn
if / when (conditional, not a question word)
unterschreiben
to sign
kopieren
to copy
Questions & Answers about Können Sie das Dokument kopieren, wenn der Chef es unterschreibt?
Why is unterschreibt at the very end of the sentence?
The word wenn is a subordinating conjunction. This means it creates a dependent clause and kicks its conjugated verb, unterschreibt, to the very end of that clause.
The translation says "when", but doesn't wenn usually mean "if"?
wenn can mean both "if" (a condition) and "when" (a present or future event). In this sentence, both meanings make perfect sense! Just remember that you cannot use wann here, because wann is only used to ask "at what time?".
What does the es refer to in the second part of the sentence?
It refers back to das Dokument. Since Dokument is a neuter noun (it uses das), you must use the neuter pronoun es to say "it". If the boss were signing a masculine noun like der Brief (the letter), you would have to use ihn instead.
Why does the first part of the sentence start with Können?
Because the main clause is a yes/no question. In German yes/no questions, the conjugated verb (Können) takes the first position, while the infinitive verb (kopieren) waits at the end of that clause. The wenn clause then simply attaches after the comma.
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