Я не знаю, дочитал ли он книгу до конца.

Questions & Answers about Я не знаю, дочитал ли он книгу до конца.

What exactly does the prefix до- add to the verb читать here?
The prefix до- adds the meaning of finishing an action or bringing it to a specific limit. While a standard perfective verb like прочитать just means you read a book completely, дочитать specifically emphasizes the process of reading until a certain point or finishing the remainder of something you started earlier.
Since дочитал already implies reading to a limit, isn't adding до конца redundant?
It might seem redundant to an English speaker, but this is a very common structure in Russian! Verbs with the до- prefix are frequently paired with the preposition до (meaning 'up to' or 'until') followed by the genitive case. The verb tells you the action was brought to a limit, and до конца explicitly defines that limit as 'the end'.
Why do we use ли here instead of если for 'whether/if'?
English speakers often mix these up because both translate to 'if'. You use если only for conditional statements, where one event depends on another (like 'If he reads, I will listen'). You must use the particle ли for indirect yes/no questions, where you are expressing doubt or asking about two possibilities (like 'I don't know whether/if he read it').
Why is ли placed after дочитал instead of at the very beginning of the clause?
In Russian, the particle ли cannot be the first word in its clause. It must immediately follow the specific word that is being questioned or doubted. Since the main doubt here is about the action itself—did he actually finish reading it?—ли attaches directly to the verb дочитал.

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