1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crudemixture

Chapter 2, Problem 2.52

(choose chapter or problem)

1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crudemixture of these isomers was sold as an insecticide. The insecticidal properties ofthe mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans-3,6-hexachlorocyclohexane.(a) Draw a structural formula for 1,2,3,4,5,6-hexachlorocyclohexane disregarding, for themoment, the existence of cis,trans isomerism. What is the molecular formula of thiscompound?(b) Using a planar hexagon representation for the cyclohexane ring, draw a structuralformula for lindane.(c) Draw a chair conformation for lindane and label which chlorine atoms are axial andwhich are equatorial.(d) Draw the alternative chair conformation of lindane and again label which chlorineatoms are axial and which are equatorial.(e) Which of the alternative chair conformations of lindane is more stable? Explain.