YOU SAID:
Do you know he does it when he doesn't know what he is supposed to do with it.
INTO JAPANESE
彼が何をすべきかわからないときに彼がそれをするのを知っていますか。
BACK INTO ENGLISH
Do you know he does it when he does not know what to do?
INTO JAPANESE
彼が何をすべきかわからないときに彼がそれをするのを知っていますか?
BACK INTO ENGLISH
Do you know he does it when he doesn't know what to do?
INTO JAPANESE
彼が何をすべきかわからないときに彼がそれをするのを知っていますか?
BACK INTO ENGLISH
Do you know he does it when he doesn't know what to do?
That didn't even make that much sense in English.