Answer
Yes Bob will be in jail
Work Step by Step
Distance travelled during reaction time
$S_1 = 50*0.6 = 30m$
distance travelled after applying brakes
$2aS_2 = v^2 -u^2$
$2*(-10) *S_2 = 0 - (50)^2$
$20S_2 = 2500$
$S_2 = 125m$
total distance travelled by Bob is
$S_1+S_2 = 30m +125m =155$
since distance travelled is greater than distance to nail strip, he will will caught and will be in jail.