ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Textbook Question
Chapter 5, Problem 50P
(Use models to solve this problem.)
(a) Write a conformational structure for the most stable conformation of trans-1,4-diethylcyclohexane and for its mirror image.
(b) Are these structures superposable?
(c) Do they represent enantiomers?
(d) Does trans-1,4-diethylcyclohexane have a stereoisomer, and if so, what is it?
(e) Is this stereoisomer chiral?
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Consider 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?
Draw 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.
(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group?
(b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
Chapter 5 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 5 - Prob. 1PPCh. 5 - Prob. 2PPCh. 5 - Prob. 3PPCh. 5 - Prob. 4PPCh. 5 - Prob. 5PPCh. 5 - Prob. 6PPCh. 5 - Prob. 7PPCh. 5 - Practice Problem 5.8 Write three-dimensional...Ch. 5 - Prob. 9PPCh. 5 - Prob. 10PP
Ch. 5 - Practice Problem 5.11 List the substituents in...Ch. 5 - Prob. 12PPCh. 5 - Practice Problem 5.13 Tell whether the two...Ch. 5 - Prob. 14PPCh. 5 - Prob. 15PPCh. 5 - Prob. 16PPCh. 5 - Prob. 17PPCh. 5 - Prob. 18PPCh. 5 - Prob. 19PPCh. 5 - Prob. 20PPCh. 5 - Practice Problem 5.21 The following are formulas...Ch. 5 - Practice Problem 5.22 Write three-dimensional...Ch. 5 - Prob. 23PPCh. 5 - Practice Problem 5.24 Give names chat include (R)...Ch. 5 - Prob. 25PPCh. 5 - Prob. 26PPCh. 5 - Prob. 27PPCh. 5 - Prob. 28PPCh. 5 - Practice Problem 5.29 Write formulas for all of...Ch. 5 - Prob. 30PPCh. 5 - Prob. 31PPCh. 5 - Prob. 32PPCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - 5.35 Designate the (R) or (S) configuration at...Ch. 5 - Prob. 36PCh. 5 - (a) Write the structure of...Ch. 5 - Shown below are Newman projection formulas for...Ch. 5 - 5.39 Write appropriate structural formulas...Ch. 5 - Discuss whether each of the following compounds...Ch. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Compound F has the molecular formula C5H8 and is...Ch. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - For the following molecule, draw its enantiomer as...Ch. 5 - 5.49 (Use models to solve this...Ch. 5 - 5.50 (Use models to solve this...Ch. 5 - (Use models co solve this problem.) Write...Ch. 5 - 5.52 Tartaric acid was an important compound in...Ch. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 1LGPCh. 5 - Prob. 2LGPCh. 5 - Prob. 3LGP
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- 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?arrow_forward4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane. (b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the carbon-3 to carbon-4 bond. (c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation that you drew as a sawhorse representation.arrow_forward(a) which if the structure of trans-1,2-dimethylcyclopentane? (b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane? (c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane? (d) which is the more stable configuration of 1,3-dimethylcyclopentane? *Et = ethylarrow_forward
- 4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.arrow_forwardThere are four cis,trans isomers of 2-isopropyl-5-methylcyclohexanol:(a) Using a planar hexagon representation for the cyclohexane ring, draw structural formulas for the four cis,trans isomers.(b) Draw the more stable chair conformation for each of your answers in part (a).(c) Of the four cis,trans isomers, which is most stable? (Hint: If you answered thispart correctly, you picked the isomer found in nature and given the name menthol.)arrow_forwardHelparrow_forward
- 3B. 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_forward(a) Draw the most stable chair conformers of trans-1,3-diisopropylcyclohexane and trans-1,4-diisopropylcyclohexane. (b) Which is more stable: trans-1,3-diisopropylcyclohexane or trans-1,4-diisopropylcyclohexane?arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- Draw each compound in its most stable conformation(s). Then draw it in its most symmetric conformation, and determine whether it is chiral.(a) 2-methylbutanearrow_forward(a) A phenyl group has the molecular formula CH- and is represented by the symbol Bn. True False (b) Para substituents occupy adjacent carbons on a benzene ring. (c) True False (e) 3-Bromobenzoic acid can be separated into cis and trans isomers. True O False (d) 1-Phenylcyclohexene is a planar molecule. True False Benzene, naphthalene, and phenanthrene are polynuclear aromatic hydrocarbons (PAHs). Truearrow_forward(a) All Isomers have the same molecular formulae. Explain this further. Hint what does it mean to have the same molecular formulae? (b) What is Constitutional (structural) isomerism? Hint, isomers are different, so what is different between a pair of constitutional isomers (see the chart on the last page for examples). (c) What is Conformational isomerism?arrow_forward
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