Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 5.7, Problem 21P
a. Which of the monosubstituted cyclohexanes in Table 3.9 on p. 128 has a negative·∆G°, for the conversion of an axial-substituted chair conformer to an equatorial-substituted chair conformer?
b. Which monosubstituted cyclohexane has the most negative ∆G° for this conversion?
c. Which monosubstituted cyclohexane has the greatest preference for an equatorial position?
d. Calculate ∆G° for the conversion of “axial methylcyclohexane to “equatorial” methylcyclohexane at 25°C.
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4. Ring Inversion of Substituted Cyclohexane
4.1 Two Chair Conformations of Substituted Cyclohexane Rings
boat conformation is 30
hair conformation. Thus, the equilibrium favors the chair conformations.
_kJ/mol higher
●
●
When Ring Flipping Occurs
If a substituent is initially in the axial position, after ring flipping it will be in the
position (and vice-versa).
equatorial
4
5
5
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The cis-trans relationships do NOT change (cis groups stay cis and trans groups stay
trans.)
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Chapter 5 Solutions
Organic Chemistry
Ch. 5.1 - Determine the degree of unsaturation and then draw...Ch. 5.1 - Prob. 4PCh. 5.2 - Prob. 5PCh. 5.2 - Draw the structure for each of the following: a....Ch. 5.2 - What is each compounds systematic name?Ch. 5.4 - Assign relative priorities to each set of...Ch. 5.4 - Tamoxifen slows the growth of some breast tumors...Ch. 5.4 - Draw and label the E and Z isomers for each of the...Ch. 5.4 - Prob. 12PCh. 5.4 - Name each of the following:
Ch. 5.4 - Prob. 14PCh. 5.4 - Prob. 15PCh. 5.6 - Prob. 16PCh. 5.6 - Prob. 17PCh. 5.6 - Prob. 18PCh. 5.6 - Prob. 20PCh. 5.7 - a. Which of the monosubstituted cyclohexanes in...Ch. 5.7 - a. for which reaction in each set will S be more...Ch. 5.7 - a. For a reaction with H = 12 kcal/ mol and S =...Ch. 5.7 - Prob. 25PCh. 5.7 - Prob. 26PCh. 5.7 - Prob. 27PCh. 5.9 - The rate constant for a reaction can be increased...Ch. 5.9 - Prob. 30PCh. 5.9 - a. Which reaction has a greater equilibrium...Ch. 5.10 - Draw a reaction coordinate diagram for a two-step...Ch. 5.10 - a. Which step in the reaction coordinate diagram...Ch. 5.10 - Draw a reaction coordinate diagram for the...Ch. 5.11 - Prob. 35PCh. 5 - What is each compounds systematic name?Ch. 5 - Draw the structure of a hydrocarbon that has six...Ch. 5 - Draw the condensed structure for each of the...Ch. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Name the following:Ch. 5 - Prob. 42PCh. 5 - 43. Draw the skeletal structure of...Ch. 5 - In a reaction in which reactant A is in...Ch. 5 - Which bond is stronger? Briefly explain why.Ch. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Assign relative priorities to each set of...Ch. 5 - Prob. 49PCh. 5 - By following the curved red arrows, draw the...Ch. 5 - Prob. 51PCh. 5 - Draw structures for the following: a....Ch. 5 - Prob. 53PCh. 5 - a. Which of the following reactions has the larger...Ch. 5 - a. What is the equilibrium constant for a reaction...Ch. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Given that the free energy of the twist-boat...Ch. 5 - Prob. 59PCh. 5 - Prob. 1PCh. 5 - Prob. 2PCh. 5 - Prob. 3PCh. 5 - Prob. 4PCh. 5 - Prob. 5PCh. 5 - Prob. 6PCh. 5 - Draw curved arrows to show the movement of the...Ch. 5 - Prob. 8PCh. 5 - Prob. 9PCh. 5 - Prob. 10P
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