Note that the work done by friction is always negative, because for any part of the journey the force is opposite to the displacement.
Next, we need to find the force.
F = µ N = µ m g = 0.23 * 3.1 * 9.8 N = 7.0 N
Then for each of the scenarios you need to multiply the force by the path length (and do not forget the negative sign!)
WFric-3 = - 7.0 N * 7 m = - 49 J
WFric-23 = - 7.0 N * 10 m = - 70 J
WFric-12 = - 7.0 N * 14 m = - 98 J
WFric-11 = - 7.0 N * 22 m = - 154 J
The take-home message of this exercise is to demonstrate that the force of friction is unlike the force of gravity, where the work only depends of the starting and ending points and is independent of the path. In other words friction is NOT a conservative force, hence path matters.