Chapter 14.6, Problem 12P

For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d. Which isomer, cis or trans, is more stable and why? [1] [2] [3]

Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?

Given the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C. A CH3 How is Compound A related to the chair conformation? H. O It is a stereoisomer. H3C- O It is a constitutional isomer. O It is a conformation isomer (conformer). H O It is not an isomer. B How is Compound B related to the chair conformation? H3C H3C- O It is a conformation isomer (conformer). O It is a stereoisomer. O It is a constitutional isomer. O It is not an isomer. CH3 How is Compound C related to the chair conformation? H3C. O It is a conformation isomer (conformer). H O It is not an isomer. ČH3 O It is a constitutional isomer. O It is a stereoisomer D How is Compound D related to the chair conformation? H3C. -CH3 O It is a stereoisomer. O It is not an isomer. H. O It is a conformation isomer (conformer). O It is a constitutional isomer.

rotation here a. Draw the three staggered and three eclipsed conformations that result from rotation around the designated bond using Newman projections. b. Label the most stable and least stable conformation. CH3-C-CH,CH3

4. Draw the most and least stable conformations of the following substituted cyclohexanes in the chair format (excluding transient conformations like half chair, twist boat and boat). Br BL Br Br

2. Circle the compound that would have the lowest energy at its most stable conformation and box the compound that would have the highest energy at its most stable conformation. 호호호호

When two six-membered rings share a C—C bond, this bicyclic system is called a decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on thesame side.a.Draw trans- and cis-decalin using the chair form for the cyclohexane rings. b.The trans isomer is more stable. Explain why.

For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents. b.Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?

Classify each compound as identical to A or its enantiomer. CHO CHO H OH CHO a. CH,CH-C--OH CumCH,CH3 H OH b. d. HO C. ČH,CH3 н он CH;CH CHO CHO A