How to say the boy took great pains to solve the quiz. in Japanese

1)少年少年(shounen) (n) boy/juvenile/young boy/youth/ladは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighクイズクイズ(kuizu) (n) quizを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,解く解く(toku) (v5k,vt) to untie/to unfasten/to unwrap/to undo/to unbind/to unpack/to unsew/to unstitch/to solve/to work out/to answer/to dispel/to clear up/to remove/to appease/to dissolve/to cancel/to remove/to lift/to raise/to release/to relieve/to dismissのにのに(noni) (prt) although/when/and yet/despite this/in spite of/even though/but even so/but even then/however/nevertheless/for all that/notwithstanding that/while/if only/i wish/i tell you/you should do/in order toかなりかなり(kanari) (adj-na,adv) considerably/fairly/quite苦労苦労(kurou) (adj-na,n,vs) troubles/hardshipsしたした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
shounen ha kuizu wo toku nonikanari kurou shita 。
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2)そのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location少年少年(shounen) (n) boy/juvenile/young boy/youth/lad(int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh(n,adj-na) sparse/not closeの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates questionクイズクイズ(kuizu) (n) quizを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,解く解く(toku) (v5k,vt) to untie/to unfasten/to unwrap/to undo/to unbind/to unpack/to unsew/to unstitch/to solve/to work out/to answer/to dispel/to clear up/to remove/to appease/to dissolve/to cancel/to remove/to lift/to raise/to release/to relieve/to dismissのにのに(noni) (prt) although/when/and yet/despite this/in spite of/even though/but even so/but even then/however/nevertheless/for all that/notwithstanding that/while/if only/i wish/i tell you/you should do/in order to骨(hone) (n) knack/skill/trick/secret/know-how/the ropes/hangを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,折ったno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
sono shounen hasono kuizu wo toku noni hone wo otta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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