Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 4, Problem 43P
Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable:
(a) cis-1-tert-butyl-3-methylcyclohexane
(b) trans-1-tert-butyl-3-methylcyclohexane
(c) trans-1-tert-butyl-4-methylcyclohexane
(d) cis-1-tert-butyl-4-methylcyclohexane
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Write the two chair conformations of each of the following and in each part designate whichconformation would be the more stable: (a) cis-1-tert-butyl-3-methylcyclohexane, (b) trans-1-tert-butyl-3-methylcyclohexane, (c) trans-1-tert-butyl-4-methylcyclohexane, ( d) cis-1-tert-butyl-4-methylcyclohexane.
4.For each of the following disubstituted cyclohexanes,
indicate whether the substituents in the two chair
conformations would be both equatorial in one chair
conformer and both axial in the other, or one equatorial
and one axial in each of the two chair conformers.
(a) Cis-1,2-
(b) Trans-1,2-
(c) Cis-1,3-
(d) Trans-1,3-
(e) Cis-1,4-
(f) Trans-1,4-
Draw the alternative chair conformations for the cis and
trans isomers of 1,2-dimethylcyclohexane, 1,3-
dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a
) Indicate by a label whether each methyl group is axial
or equatorial. (b) For which isomer(s) are the alternative
chair conformations of equal stability? (c) For which
isomer(s) is one chair conformation more stable than
the other?
Chapter 4 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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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- Write the two chair conformations of each of the following and in each part designate which conformation would be more stable. Why?a) trans-1-tert-butyl-3-methylcyclohexaneb) trans-1-tert-butyl-4-methylcyclohexanearrow_forwardCyclohexane 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_forwardWrite the structures of two chair conformations of 1-tert-butyl-1-methylcyclohexane. Which conformation is more stable?arrow_forward
- Draw a chair conformer and the ring-flipped conformed and determine which conformer for each pair you drew in part(a) is more stable. (i) 1-tert-butyl-1-methylcyclohexane (ii) cis-1-tert-butyl-3-methylcyclohexanearrow_forwardDraw the most stable conformation of cis-1-tert-butyl-3-ethylcyclohexane. (a) (b) trans-1-tert-butyl-2-methylcyclohexane. (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward
- Draw the most stable chair conformation of each of the following compounds. (a) cis-1,1,4- trimethylcyclohexane (B) trans -1,1,3-trimethylcyclohexane (c) cis -1 fluro-4-ethylcyclohexane -arrow_forwardGiven the structures of the following two tetramethylcyclohexanes: CH3 CH3 CH3 "CH3 CH3 CH3 A В (a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy (most stable)? (b) Ring flip the above structures and draw the least stable chair conformation for both A and B. Which structure is highest in energy (least stable)?arrow_forwardFollowing are the alternative chair conformations for trans-1,2-dimethylcyclohexane.(a) Estimate the difference in free energy between these two conformations.(b) Given your value in (a), calculate the percent of each chair present in anequilibrium mixture of the two at 25°C.arrow_forward
- H C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. b) Which staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy which has the highest energy?arrow_forward3B. For each compound below, draw two chair conformations. Indicate whether the substituents are axial or equatorial. Indicate which chair conformation is more stable. (you need to draw conformations of the exact molecule, not its mirror image or diastereomer) (a) (b) (c) Ме Me Et "Et Et Mearrow_forwardDraw both cis- and trans-1,4-dimethylcyclohexane in their more stable chair conformations. 5-72 (a) How many stereoisomers are there of cis-1,4-dimethylcyclohexane, and how many of trans-1,4-dimethylcyclohexane? (b) Are any of the structures chiral? (c) What are the stereochemical relationships among the various stereoisomers of 1,4-dimethylcyclohexane?arrow_forward
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