Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each case, determine which conformation is more stable.
e. cis-1-ethyl-4-methylcyclohexane
f. trans-1-ethyl-4-methylcyclohexane
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Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each case, determine which conformation is more stable.
e. cis-1-ethyl-4-methylcyclohexane
f. trans-1-ethyl-4-methylcyclohexane
Conformational studies on ethane-1,2-diol (HOCH2–CH2OH) have shown the most stable conformation about the central C―C bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers, and explain this curious result.
Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name.
(a)
(b)
Draw Newman projections along the C3―C4 bond to show the most stable and least stable conformations of 3-ethyl-2,4,4-trimethylheptane.
Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name. g.
(g)
(h)
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.