Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 3.15A, Problem 3.29P
Draw the two chair conformations of each of the following substituted cyclohexanes. In each case, label the more stable conformation.
- a. cis-1-ethyl-2-methylcyclohexane
- b. trans-1,2-diethylcyclohexane
- c. cis-1-ethyl-4-isopropylcyclohexane
- d. trans-1-ethyl-4-methylcyclohexane
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Consider the tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each six-membered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.
Draw the planar (Haworth) structure for cis-1-ethyl-2- methylcyclohexane. (b) Draw the two ring - flipped chair conformations. (c) Circle the more stable chair conformation (circle both if they are equal in energy). Draw the Haworth structure and the two ring-flipped conformations of 1, 2, 4- trimethylcyclohexane (Compound D) on the frames below, b) Circle the more stable chair conformation (circle both if they are equal in energy). Haworth Structure
Draw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description.
a.a 1,1-disubstituted cyclohexane with an axial CH3CH2 group
b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group
c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group
d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 group.
Chapter 3 Solutions
Organic Chemistry (9th Edition)
Ch. 3.2 - Using the general molecular formula for alkanes:...Ch. 3.3B - Name the following alkanes and haloalkanes. When...Ch. 3.3B - Write structures for the following compounds. a....Ch. 3.3B - Provide IUPAC names for the following compounds....Ch. 3.3B - Prob. 3.5PCh. 3.3B - Prob. 3.6PCh. 3.3B - Prob. 3.7PCh. 3.3B - Draw the structures of the following compounds. a....Ch. 3.3B - Without looking at the structures, give molecular...Ch. 3.4C - Prob. 3.10P
Ch. 3.7B - Prob. 3.11PCh. 3.7C - Draw a graph similar to Figure 3-9, of the...Ch. 3.8B - Draw a graph similar to Figure 3-11, of the...Ch. 3.9 - Draw a perspective representation of the most...Ch. 3.10C - Give IUPAC names for the following compounds.Ch. 3.10C - Draw the structure and give the molecular formula...Ch. 3.11 - Which of the following cycloalkanes are capable of...Ch. 3.11 - Give IUPAC names for the following cycloalkanes.Ch. 3.12B - The heat of combustion of...Ch. 3.12C - Prob. 3.20PCh. 3.13B - The cyclohexane chair shown in Figure 3-22 has the...Ch. 3.13B - Draw 1,2,3,4,5,6-hexamethylcyclohexane with all...Ch. 3.14 - Prob. 3.23PCh. 3.14 - Prob. 3.24PCh. 3.14 - Draw the most stable conformation of a....Ch. 3.15 - Prob. 3.26PCh. 3.15 - a. Draw both chair conformations of cis-1...Ch. 3.15 - Prob. 3.28PCh. 3.15A - Draw the two chair conformations of each of the...Ch. 3.15B - Draw the most stable conformation of a....Ch. 3.16A - Name the following compounds.Ch. 3.16B - Prob. 3.32PCh. 3 - Prob. 3.33SPCh. 3 - Prob. 3.34SPCh. 3 - 3-35 a. Draw and name the five cycloalkane...Ch. 3 - Draw the structure that corresponds with each...Ch. 3 - Each of the following descriptions applies to more...Ch. 3 - Write structures for a homologous series of...Ch. 3 - Prob. 3.39SPCh. 3 - Construct a graph, similar to Figure 3-11, of the...Ch. 3 - The following names are all incorrect or...Ch. 3 - In each pair of compounds, which compound has the...Ch. 3 - There are eight different five-carbon alkyl...Ch. 3 - Use a Newman projection about the indicated bond...Ch. 3 - a. Draw the two chair conformations of...Ch. 3 - Draw the two chair conformations of each compound,...Ch. 3 - Using what you know about the conformational...Ch. 3 - Prob. 3.48SPCh. 3 - Draw Newman projections along the C3C4 bond to...Ch. 3 - Prob. 3.50SPCh. 3 - The most stable form of the common sugar glucose...Ch. 3 - This is a Newman projection of a substituted...
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- On the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25). (a) Convert the stereorepresentation on the left to a planar hexagon representation. (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?arrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?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
- Consider the attached tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each sixmembered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.arrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that ts each description.a. a 1,1-disubstituted cyclohexane with an axial CH3CH2 groupb. a cis-1,2-disubstituted cyclohexane with an axial CH3 groupc. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 groupd. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 grouparrow_forwardConsider the following cyclohexane derivative: *Figure is the screenshot* a. Draw a chair conformation for the cyclohexane derivative above showing equatorial and axial positions at the carbon atoms bearing the substituents. b. Draw the flipped chair conformation showing the axial and equatorial position at the carbon atoms that bear the substituents. Determine which structure is more stable(8a or 8b)? Describe and give your reasons.arrow_forward
- a. Draw trans-1-ethyl-2-methylcyclohexane in its lowest energy conformation. Choose a chair from the Templates toolbar at the bottom. Make sure it’s the appropriate chair, including any heteroatoms. Replace the appropriate hydrogens with the appropriate −CH3−CH3 or other groups. b. Draw the structure that corresponds with the name: isobutylcyclopentane.arrow_forwardThere are the two possible chair conformations of trans-1-Methyl-4-chlorocyclohexane. What is the energy difference between the two chair conformations? Table 1. Steric Strain in Monosubstituted Cyclohexanes a 28 b. 56 c. 4.8 d 9.6arrow_forwarddraw most stable chair conformation of trans-1-tert-buty-3-methylcyclohexane and most stable chair conformation of cis-1-tert-buty-3-methylcyclohexane？In what way make them different？arrow_forward
- 1,3-dimethylcyclohexane can exist in a chair conformation with its substituents in the equatorial and axial positions. Which is the most preferred conformation of the compound? a. Trans-1,3-dimethylcyclohexane b. None of the choices c. Cis-(e)-1,3-dimethylcyclohexane d. Cis-(a)-1,3-dimethylcyclohexanearrow_forwardDraw the more stable chair conformation for each compound. a. trans-1-isopropyl-3-methylcyclohexane b.cis-1-sec-butyl-4-ethylcyclohexane c. cis-1-ethyl-2-isobutylcyclohexane d. trans-1,2-dibutylcyclohexanearrow_forwardWrite 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_forward
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