5 kcal mol 1 c the heat of combustion of trans and

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; fully eclipsed butane = 4.5 kcal mol -1 ). c. The heat of combustion of trans- and cis- decalin are –1500.2 kcal mol –1 and -1502.9 kcal mol –1 , respectively. Is this consistent with your conformational analysis? 8. Steroids are important signaling molecules in our bodies and are typically constructed of 4 fused rings (J&F, pg. 559- 562). The synthesis of such molecules from simpler precursor molecules requires careful planning for the construction of the fused rings and their energetic costs. Consider the isomers created from the edge-fusion of two cyclohexane rings, cis- and trans - decalin (J&F, pg. 212). a. Build models of cis- and trans -decalin in which each six-membered ring is in a chair conformation (the lowest energy form). Which system can undergo a ring flip? Carefully examine the models and explain why. Draw a Newman projection for each isomer of decalin in its lowest energy conformer looking down the fused C–C bond. 9. Draw 4 structural isomers of molecular formula C H Cl that each have a configurational stereoisomer. Provide the Chem 33, Kanan & Stack, 2012, PS 4; pg 4
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10. The connectivity of menthol is shown below. a. Draw the most stable chair conformations of the 1R,2S,5R stereoisomer (natural menthol), the 1 S,2R,5R
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