Step 1: Start from the fundamental canonical commutation relation:
\[ [x, p_x] = i\hbar. \]
Step 2: Use the operator identity \([AB, C] = A[B, C] + [A, C]B\) with \(A = B = x\) and \(C = p_x\):
\[ [x^2, p_x] = x[x, p_x] + [x, p_x]x. \]
Step 3: Substitute \([x, p_x] = i\hbar\):
\[ [x^2, p_x] = x(i\hbar) + (i\hbar)x = 2i\hbar x. \]
(The extra \(\pi\) written in the printed stem is a typographical artifact; the commutator itself evaluates to the following.)
\[ \boxed{[x^2, p_x] = 2i\hbar x} \]