YOU SAID:
The old woman killed the old man wondering if I will go to jail.
INTO JAPANESE
老婦人は私が刑務所に行くかどうか疑問に思って老人を殺しました。
BACK INTO ENGLISH
The old lady wondered if I would go to jail and killed the old man.
INTO JAPANESE
老婦人は私が刑務所に行き、老人を殺すかどうか疑問に思いました。
BACK INTO ENGLISH
The old lady wondered if I would go to jail and kill the old man.
INTO JAPANESE
老婦人は私が刑務所に行って老人を殺すかどうか疑問に思いました。
BACK INTO ENGLISH
The old lady wondered if I would go to jail and kill the old man.
That didn't even make that much sense in English.