YOU SAID:
What time does Jack get off from work?
INTO JAPANESE
ジャックは何時から仕事をやめますか?
BACK INTO ENGLISH
What time will Jack quit his job?
INTO JAPANESE
ジャックは何時に仕事をやめるのだろう?
BACK INTO ENGLISH
What time will Jack quit his job?
That didn't even make that much sense in English.