Yes,when Frieza killed Krillin on Dragon Ball Z Kai.
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Gohan is stronger if goku is in his normal form but if they are both in super saiyan 2 form or if Goku is in super saiyan form then goku is stronger.
Goku does not turn super saiyan 6 or 5 in fact. and it only goes up to super saiyan 3 in the manga and super saiyan 4 in the cartoon.
160 is when he first went super saiyan 2 after training with goku (his dad) as a super saiyan 1 he was angry because cell killed so many people and killed one right in front of him so he got angry and went SUPER SAIYAN 2. P.S super saiyan 2 is the highest super saiyan gohan can do but in dragon ball AF gohan goes super saiyan 4 and goku goes super saiyan 50 that is all i can tell you.
you dont get him to be his form forever u need to get the orb in goku to go super saiyan
frieza killed krillin on planet namek when goku tried to hit him with the spirit bomb but failed also when krillin was killed goku turned super saiyan for the first time