For 1-bromobutane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.

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Use a Newman projection to show the most stable conformation of 3,4-dimethylhexane as you look down thebond between carbons 2 and 3.

Draw tert-butylcyclohexane in the chair conformation, then perform a ring flip on your 1st drawing to give your second chair conformation. Label the tert-butyl group as axial or equatorial. Label the conformation that is more stable.

6. Draw the chair conformation and its ring-interconversion isomer of both cis and trans-1-cyclobutyl-2- methylcyclohexane and rank the four structures for stability (1 = most stable to 4 = least stable; no justifications needed). Don't forget to draw in your cyclohexane ring hydrogens!

4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: # higher energy conformation: most stable conformation: higher energy conformation: 00 Do po

Draw 2,4-dimethylhexane as a bond-line structure. Then, looking down the C3 – C4 bond, draw a Newman projection representation of the 1) lowest energy (most stable) and 2) highest energy (least stable) conformations.

Draw the Newman projections for one staggered and one eclipsed conformation of 2,2-dimethylheptane, viewed down the bond from C3 to C4.

C. Using your molecular modeling kit, construct cis-1,4-dimethylcyclohexane. In the space below, draw one of the chair conformations. Label the methyl groups as either axial (a) or equatorial (e). Number the carbons of the cyclohexane ring, perform a chair flip and draw the new chair conformation.

Consider the cyclohexane framework in a chair conformation, where carbon 1 has two substituents, X and Y. a. Label each position as axial or equatorial. b. On the same figure, label all positions that are gauche to the Y group on carbon 1. A bin may hold more than one label. axial equatorial X 1 equatorial equatorial 2 axial axial axial gauche 3 axial gauche 5 equatorial equatorial 4 axial equatorial Answer Bank equatorial gauche axial