Mark M. answered 05/15/15
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Retired math prof. Very extensive Precalculus tutoring experience.
Tan(5π/8) = Tan [(5π/4)/2]
Tan(θ/2) = ±√{(1 - cosθ)/(1 + cosθ)}
Since 5π/8 lies in quadrant 2, tan (5π/8) < 0
tan (5π/8)=tan[(5π/4)/2)=-√{(1 - cos(5π/4))/(1 + cos(5π/4))}
= -√{(1 + √2/2)/(1 - √2/2)}
= -√{(2 + √2)/(2 - √2)}