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Chapter 4: 4-21 (page 90)
Look at the following structure of the female hormone estrone, and tell whether each of the two indicated ring-fusions is cis or trans.
Both structures have trans-ring fusions.
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Cis-decalin is less stable than trans-decalin. Assume that the 1,3-diaxial interactions in cis-decalin are similar to those in axial methylcyclohexane [that is, one CH H interaction costs 3.8 kJ/mol (0.9 kcal/mol)], and calculate the magnitude of the energy difference between cis- and trans-decalin.
Draw three isomers of trans-1, 2-dichlorocyclobutane, and label them as either constitutional isomers or stereoisomers.
Question:There are two different substances named trans-1,2-dimethylcyclopentane. What is the relationship between them?
Why do you suppose an axial cyano (–CN) substituent causes practically no 1,3-diaxial steric strain (0.4 kJ/mol)? Use molecular models to help with your answer.
Assume that you have a variety of cyclohexane substituted in the positions indicated. Identify the substituents as either axial or equatorial. For example, a 1, 2-cis relationship means that one substituent must be axial and one equatorial, whereas a 1, 2-trans relationship means that either substituent is axial or both are equatorial.
(a) 1, 3-Trans disubstituted (b) 1, 4-Cis disubstituted
(c) 1, 3-Cis disubstituted (d) 1, 5-Trans disubstituted
(e) 1, 5-Cis disubstituted (f) 1, 6-Trans disubstituted
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