Tan(π/2) is undefined; thus making the expression undefined.
However, if you are willing to play with the expression, you can do this:
tan(π/2) = sin(π/2) / cos(π/2)
1 - tan²(π/2) = sec²(π/2) = 1 / cos²(π/2)
So: 2·tan(π/2) / [1 - tan²(π/2) ] = [ 2·sin(π/2) / cos(π/2) ] / [ 1 / cos²(π/2) ]
= [ 2·sin(π/2) / cos(π/2) ] · [ 1 / cos²(π/2) ]
= 2·sin(π/2)·cos(π/2) Since sin(2x) = 2xin(x)cos(x):
= sin(2 · π/2) = sin(π) = 0