Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 3.46SP
Draw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each case, determine which conformation is more stable.
- a. cis-1-ethyl-2-isopropylcyclohexane
- b. trans-1-ethyl-2-isopropylcyclohexane
- c. cis-1-ethyl-3-methylcyclohexane
- d. trans-1-ethyl-3-methylcyclohexane
- e. cis-1 -ethyl-4-methylcyclohexane
- f. 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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- Following 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_forwardOn 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_forward1,3-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_forward
- 3 1. construct an energy diagram to show the variation in the free energy of the molecule as the front atom is rotated clockwise from 0 degrees to 360 degrees in 60 degrees increments. in your energy diagram you should clearly show the relative energies of each conformer 2. draw newman projections for each conformation in the bottom of your diagramarrow_forwardDraw the two chair conformations of each compound, and label the substituents as axial and equatorial. In each case, determine which conformation is more stable. a) trans-1-ethyl-3-methylcyclohexanearrow_forwardFor each compound drawn below: a.Label each OH, Br, and CH3 group as axial or equatorial. b.Classify each conformation as cis or trans.c.Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring. d. Draw the second possible chair conformation for each compound.arrow_forward
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