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I have some confusion about placement of direct objects (DO) and indirect objects (IO) in spanish sentences, especially with complex verbs.

I understand the IO and DO come after the subject pronoun, and after negation (like in "no"), and before conjugated verbs. They can also be placed after infinitive verbs.

Which of the following is correct, and which is also preferred, or more commonly used, for the phrase "You prefer to give it to him" ?

prefieres darselo

se lo prefieres dar

se prefieres darlo

Also, are there cases when an object pronoun would be placed between the conjugated and infinitive verbs?

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Of the three permutations you tried, the first two work great:

  • Prefieres dárselo.

  • Se lo prefieres dar.

The other one doesn't work. The two object pronouns can't be separated that way.

In terms of choosing between the first two sentences, there aren't any hard and fast rules. You can choose whichever feels more comfortable to you with the particular sentence.

For your last question: an object pronoun should not be inserted between a conjugated verb and an infinitive. To be clear, an object pronoun should not come after a conjugated verb (unless it's an imperative), regardless of whether there's an infinitive after it. It's not wrong, but it's not done nowadays. (It used to be common centuries ago and can still be found in some very formal contexts. So a sentence like "Prefiéresselo dar" is grammatically correct, but save for very few regional variants, no one speaks or writes like that nowadays. For all practical purposes, you can forget about that alternative.)

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  • Although it's not usual nowadays, one can insert an object pronoun between a finite verb and an infinitive: "Puédeslo comer" is grammatical, as well as "Dejáronmelo hacer" and other like that. It's just that people don't talk like that anymore.
    – pablodf76
    Jan 30, 2020 at 19:30
  • @pablodf76 - Ah, interesting. // For a learner (beginner to intermediate), is it okay to tell them that it doesn't work? If not, could you edit my answer? Jan 30, 2020 at 22:26
  • I've edited your answer as requested. Please check if it's alright with you.
    – pablodf76
    Jan 31, 2020 at 13:06
  • "no-one speaks like that" — entran los gallegos y asturianos… Jan 31, 2020 at 14:39
  • @user0721090601 - Is that better? Jan 31, 2020 at 16:53

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