Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 5, Problem 39P
Given that the twist-boat conformer of cyclohexane is 5.3 kcal/mol higher in free energy than the chair conformer, calculate the percentage of twist-boat conformers present in a sample of cyclohexane at 25 °C. Does your answer agree with the statement made on page 103 about the relative number of molecules in these two conformations?
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Chapter 5 Solutions
Essential Organic Chemistry, Global Edition
Ch. 5.1 - Prob. 1PCh. 5.1 - Draw the structure for each of the following: a....Ch. 5.1 - What is each compounds systematic name?Ch. 5.3 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.3 - Prob. 7PCh. 5.4 - a. For which reaction in each set below will S be...Ch. 5.6 - Prob. 9PCh. 5.6 - How many different alkenes can be hydrogenated to...Ch. 5.6 - The same alkane is obtained from the catalytic...
Ch. 5.6 - Prob. 12PCh. 5.6 - Rank the following compounds in order from most...Ch. 5.7 - The rate constant for a reaction can be increased...Ch. 5.7 - Prob. 15PCh. 5.7 - Prob. 16PCh. 5.9 - Draw a reaction coordinate diagram for a two-step...Ch. 5.9 - Prob. 18PCh. 5.9 - Draw a reaction coordinate diagram for the...Ch. 5.10 - Which of the following parameters would be...Ch. 5 - What is each compounds systematic name?Ch. 5 - Draw the structure of a hydrocarbon that has six...Ch. 5 - Which of the following compounds is the most...Ch. 5 - Prob. 24PCh. 5 - Prob. 25PCh. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Name the following:Ch. 5 - Prob. 29PCh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Name each of the following:Ch. 5 - Prob. 38PCh. 5 - Given that the twist-boat conformer of cyclohexane...Ch. 5 - a. The G for conversion of axial fluorocyclohexane...Ch. 5 - Prob. 1PCh. 5 - Prob. 2PCh. 5 - Prob. 3PCh. 5 - Prob. 4PCh. 5 - Prob. 5PCh. 5 - Prob. 6PCh. 5 - Prob. 7PCh. 5 - Prob. 8PCh. 5 - Prob. 9PCh. 5 - Prob. 10P
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- 7. Draw the two chair conformations for the molecule below. Given the corresponding energy values, place the conformations in the appropriate boxes. Substituent AG° (eq→ ax) (kcal/mol) -CN -CH, 0.2 NEC 1.7 less stable chair more stable chair Clearly explain why the energy barrier associated with a nitrile group (-CN) moving from an equatorial position to an axial position is much lower than for a methyl group (-CH3).arrow_forwardThe chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C-1¬C-2 bond?arrow_forward8. For each of the following compounds, draw the most stable conformation and indicate the number of gauche and 1,3-diaxial interactions present. For molecules that can exist in another chair conformation, estimate the energy difference between the two forms (gauche interactions = 0.9 kcal/mol; 1,3-diaxial Me-Me interactions = 3.7 kcal/mol). H3C H3C H3C CH3 "CH3 a b C CH3 CH3 CH3 H3C H3C d earrow_forward
- The following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?arrow_forwardOn a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.arrow_forwardDraw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forward
- Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.arrow_forwardWhich of the statements below correctly describes the chair conformations of trans-1,4-dimethylcyclohexane? * The lower energy chair conformation contains two axial methyl groups. The two chair conformations are of equal energy. The higher energy chair conformation contains one axial methyl group and one equatorial methyl group. O The higher energy chair conformation contains two axial methyl groups. The lower energy chair conformation contains one axial methyl group and one equatorial methyl group.arrow_forwardRank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable. To rank items as equivalent, overlap them.arrow_forward
- O B. 01 H₂C O. C. O A. O D. For the following structural formula, pick the structure that accurately represents its MOST STABLE conformation. Br CHS A Br CH3 B H₂CH CH3 CH3 Cill Br H₂C Br с CH₂3 H₂C Br. CH3 D hparrow_forwardIn the drawing areas below, draw the two conformations of trans-1 - fluoro -2-iodocyclohexane that are typically the most stable. Be sure your drawings make it possible to distinguish between the conformations. After you've drawn the conformations, answer the question below the drawing areas. PLEASE DRAW 2 STABLE CHAIR FLIPS AND CHOOSE THE MOST STABLE ONE. In the drawing areas below, draw the two conformations of trans-1-fluoro-2-iodocyclohexane that are typically the most stable. Be sure your drawings make it possible to distinguish between the conformations. After you've drawn the conformations, answer the question below the drawing areas. 口 Ö Click and drag to start drawing a a structure. 5 Of the two conformations you drew above, which is the more stable? Olaft © Rudo 口 x 5 chair flip Click and drag to start drawing a s a structure. they are equally stable cannot decide without more information x Q m W 田arrow_forwardDraw all the possible conformations of trans- and cis-1,3-dimethylcyclobutane. Which of these conformations is the most stable conformation? Explain your answer. Discuss the type of strain(s) that affect the stability of these compounds.arrow_forward
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