How to say the problem perplexed him. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighそのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location問題問題(mondai) (n) problem/questionで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.困ってno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbいるいる(iru) (v1,vi) to be/to exist/to stay/ verb indicating continuing action or state。(。) Japanese period "."    
kareha sono mondai de komatte iru 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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2)そのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location問題問題(mondai) (n) problem/questionは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/that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,悩まno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbせたno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
sono mondai ha kare wo nayama seta 。
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