Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 4, Problem 47P
Consider the cis and trans isomers of 1,3-di-tert-butylcyclohexane (build molecular models). What unusual feature accounts for the face that one of these isomers apparently exists in a twist boat conformation rather than a chair conformation?
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Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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- The diaxial conformation of cis-1, 3-dimethylcyclohexane is approximately 23 kJ/mol (5.4 kcal/mol) less stable than the diequatorial conformation. Draw the two possible chair conformations, and suggest a reason for the large energy difference.arrow_forwardFill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.arrow_forward- What is Keq for the two possible chair conformations? (cis-1,2-dimethylcyclohexane.) Explain how you arrived to the answer.arrow_forward
- Give the most stable conformation for (1S, 2S)-1-methoxy-2-chlorocyclohexane.arrow_forwardMeasure the C-C-C and C-C-H bond angles in the energy-minimized models of cis and trans isomers of cyclooctene. Compare these values with those predicted by VSEPR. In which isomer are deviations from VSEPR predictions greater?arrow_forwardDiscuss and compare two possible chair conformations of cis-1,3-dibromocyclohexane compound. Which conformation is more stable? Why? Explain the reason clearly.arrow_forward
- In the lowest energy chair conformation of cis-1,3-dimethylcyclohexane, how many axial positions are occupied by methyl groups?arrow_forwardCalculate the difference in energy between the two conformation of trans_4_tert_butyl_1_methylcyclohexanearrow_forwardDescribe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forward
- Draw Newman projection formula for the distinct conformation of 1,2-dichoroethane, label them as a, b, c, and d, and predict their relative energies. Additionally, state whether their geometry is staggered or eclipsed.arrow_forwardUsing your model, construct an energy diagram to show the variation in the free energy of the molecule as the FRONT ATOM is rotated CLOCKWISE from 0º to 360º in 60º increments. In your energy diagram, you should clearly show the relative energies of each conformer.arrow_forwardDraw the two chair conformations for cis-1,2-dimethylcyclohexane and label all positions clearly as equatorial and axial. Label the most stable and least stable conformation and explain the reasonarrow_forward
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