Can smoothing a single crossing in a diagram for a knot convert it into a diagram of the knot's mirror image? Zeković found such a smoothing for the torus knot T(2, 5), and Moore–Vazquez proved that such smoothings do not exist for other torus knots T(2, m) with m odd and square free. The existence of such a smoothing implies that K # K bounds a Mobius band in B4. We use Casson–Gordon theory to provide new obstructions to the existence of such chiral smoothings. In particular, we remove the constraint that m be square free in the Moore–Vazquez theorem, with the exception of m = 9, which remains an open case. Heegaard Floer theory provides further obstructions; these do not give new information in the case of torus knots of the form T(2, m), but they do provide strong constraints for other families of torus knots. A more general question asks, for each pair of knots K and J, what is the minimum number of smoothings that are required to convert a diagram of K into one for J. The methods presented here can be applied to provide lower bounds on this number.