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Old February 17, 2017, 07:03 AM
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aleCcowaN aleCcowaN is offline
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Join Date: Aug 2010
Location: Buenos Aires, Argentina
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Native Language: Castellano
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Allow me to comment further on your original sentence, which wasn't 100% wrong; furthermore, it looks like an anacoluthon most native speakers would do every third day.

¿Cómo le enseño a mi gato que no rasguñe mis muebles?

Enseñar a, aprender a,
require a verb in noun form. It's the abstract action and nobody is doing it at any time: enseñar a no arañar.

You have also the personal a there: enseñar a mi gato.

You can link a clause starting with "que...", but you have to introduce a new verb or a new "subject" in order "clean the slate"

¿Cómo le enseño a mi gato que los muebles no se rasguñan?
¿Cómo le enseño a mi gato que no hay que rasguñar los muebles?
¿Cómo le enseño a mi gato que los muebles no están para que los raguñe?
¿Cómo le enseño a mi gato que un mueble no es un árbol con corteza?

The most common "untidy" phrase would be

¿Cómo le enseño a mi gato a que no rasguñe mis muebles?

with two a's to make it work. If you used that kind of phrases you wouldn't get a literary prize, but there's nothing more "native sounding" like that. Use it when and where you have to be sure the message went through and some lack of formality is tolerated.
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