Given the planar trisubstituted cyclohexane, fill in the missing substituents (with H or Cl) to complete the two possible cyclohexane chair conformations. Then, determine the more stable conformer. You might find it helpful to make a model of the cyclohexane to help visualize the chair conformations. & Br H. H H H H H Chair 1 Br chair flip Answer Bank H F H H H. H H H Chair 2

draw most stable and least stable conformations for each

Starting from the structure below (sighting down the indicated bond). rotate the back carbon to provide an eclipsed conformer of the structure. Ph H H HI!!! ++||||4 CH₂CH3 I I I I I I H Draw Newman Projection I I I

Do not give handwriting solution.

None

a) Draw two chair conformations and label the most stable conformation. For consistency between assignments, use the diagrams given. You may redraw but keep the orientation the same; otherwise, it becomes difficult for students to mark! I have added the Br to carbon 1 for the first chair conformation as a start. b) What is the dihedral angle between the chlorine atom and the methyl group in the most stable chair conformation. total for for correct drawing correct drawing for Br correct angle Br dihedral 1 angle = CI" 4 CH3 H *** : for identifying most stable

In kcal/mol