EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 8, Problem 8.11P
Interpretation Introduction
Interpretation:
Among the given boiling points, the correct boiling points corresponding to the stereoisomers of
Concept introduction:
The dipole moment is defined as the charge separation between two the atoms in a covalent or in an ionic bond. Polarities of atoms or ions are known by dipole moment. If the value of dipole moment is zero, then the molecule is said to be non-polar, and if the value of dipole moment is not zero, then the molecule is said to be polar and possess permanent dipole moment.
If any structure is symmetrical, then overall dipole moment will be zero, and the bond becomes non-polar. Also, a bond can be considered polar if there is some electronegativity difference between the atoms.
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From studies of the dipole moment of 1,2-dichloroethane in the gas phase at room temperature (25°C), it is estimated that the ratio of molecules in the anti conformation to gauche conformation is 7.6 to 1. Calculate the difference in Gibbs free energy between these two conformations.
The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).
Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.
Chapter 8 Solutions
EBK ORGANIC CHEMISTRY
Ch. 8 - Prob. 8.1PCh. 8 - Prob. 8.2PCh. 8 - Prob. 8.3PCh. 8 - Prob. 8.4PCh. 8 - Prob. 8.5PCh. 8 - Prob. 8.6PCh. 8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10P
Ch. 8 - Prob. 8.11PCh. 8 - Prob. 8.12PCh. 8 - Prob. 8.13PCh. 8 - Prob. 8.14PCh. 8 - Prob. 8.15PCh. 8 - Prob. 8.16PCh. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Prob. 8.20PCh. 8 - Prob. 8.21PCh. 8 - Prob. 8.22PCh. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - Prob. 8.25PCh. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28APCh. 8 - Prob. 8.29APCh. 8 - Prob. 8.30APCh. 8 - Prob. 8.31APCh. 8 - Prob. 8.32APCh. 8 - Prob. 8.33APCh. 8 - Prob. 8.34APCh. 8 - Prob. 8.35APCh. 8 - Prob. 8.36APCh. 8 - Prob. 8.37APCh. 8 - Prob. 8.38APCh. 8 - Prob. 8.39APCh. 8 - Prob. 8.40APCh. 8 - Prob. 8.41APCh. 8 - Prob. 8.42APCh. 8 - Prob. 8.43APCh. 8 - Prob. 8.44APCh. 8 - Prob. 8.45APCh. 8 - Prob. 8.46APCh. 8 - Prob. 8.47APCh. 8 - Prob. 8.48APCh. 8 - Prob. 8.49APCh. 8 - Prob. 8.50APCh. 8 - Prob. 8.51APCh. 8 - Prob. 8.52APCh. 8 - Prob. 8.53APCh. 8 - Prob. 8.54APCh. 8 - Prob. 8.55APCh. 8 - Prob. 8.56APCh. 8 - Prob. 8.57AP
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- sketch the various conformational isomers of 1,3-dimethylcyclohexane. Indicate the position (axial/equatorial) of each of the methyl groups in each structure.arrow_forwardIt is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D configuration and what conformation (axial,equatorial) would each of the three ethyl groups be in for the most stable configuration.arrow_forward4. Which of the following has a higher boiling point? Explain your answer:(a) 2-propanol or 2-butanol(b) Dimethyl ether or ethanolarrow_forward
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- When cyclohexane is substituted by an ethynyl group, -C=CH, the energy difference between axial and equatorial conformations is only 1.7 kJ (0.41 kcal)/mol. Compare the conformational equilibrium for methylcyclohexane with that for ethynylcyclohexane and account for the difference between the two.arrow_forwardHello, I was reading an answer from the book Organic Chemistry by Brown et al. The question is 2.51 "Draw alternative chair conformations for each substituted cyclohexane and state which chair is more stable." There are then 4 cyclohexanes (labeled a-d). For the "a" cyclohexane, the substituents are arranged as a combination of axial and equatorial in both chair conformations. However, for the "b," "c," and "d," cyclohexanes one chair has only equatorial substituents, and the other chair has only axial substituents. Why is the "a" chair conformation different? https://www.bartleby.com/solution-answer/chapter-2-problem-251p-organic-chemistry-8th-edition/9781305580350/draw-alternative-chair-conformations-for-each-substituted-cyclohexane-and-state-which-chair-is-more/4532cd91-c341-11e9-8385-02ee952b546earrow_forward4. Barriers to Rotation. What is the rotational barrier (that is, the energy difference between the lowest- and highest-energy conformers) for 2,2-dimethylpropane when the molecule is rotated about the C2-C3 bond?arrow_forward
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