Chapter 3: 47P (page 190)
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two isomers is more stable. Explain your reasoning.
Short Answer
Trans isomer of is more stable than cis isomer of .
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Chapter 3: 47P (page 190)
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two isomers is more stable. Explain your reasoning.
Trans isomer of is more stable than cis isomer of .
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Question: Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers
(a)
(b)
(c)
(d)
(a) Draw the two chair conformations of , and label all the positions as axial or equatorial.
(b) Label the higher-energy conformation and the lower-energy conformation.
(c) The energy difference in these two conformations has been measured to be aboutper mole. How much of this energy difference is due to the torsional energy of gauche relationships?
(d) How much energy is due to the additional steric strain of thediaxial interaction?
Question: Draw a graph, similar to Figure 3-9, of the torsional strain of as it rotates about the bond between and . Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.
Each of the following descriptions applies to more than one alkane. In each case draw and name two structures that match the description.
(a)
(b)
(c)
(d)
(e)
(f)
Question: Convert each Newman projection to the equivalent line-angle formula, and assign the IUPAC name.
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