Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3.15A, 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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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.
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
There 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 9.6
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw 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_forward4. Draw the most and least stable conformations of the following substituted cyclohexanes in the chair format (excluding transient conformations like half chair, twist boat and boat). Br BL Br Brarrow_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_forward
- • Draw the chair conformations of the following compounds and determine which geometric isomer is more stable. Also show using Newman projection that one conformation is more stable than the other. a. cis-1-isopropyl-2-methylcyclohexane b. 1-methycyclohexanearrow_forwarda. Calculate the energy difference between the two chair conformers of trans-1,4-dimethylcyclohexane. b. What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?arrow_forwardH;C-CH2-CH–CH3 CH₂-CH3 Relative to the molecule above, which of the below is not a conformer? A. C. HỌC-CH,-CH–CH, CH H₂-CH-C CH3 CH3 CH3-CH-CH-CH3 13-CH-C CH3 B. D. CH3 CH3 CH₂-CH-CH₂ CH3 CH₂ CH-CH₂-CH3 CH₂ CH3arrow_forward
- What is the correct IUPAC name for the compound shown? CH-CH-CHCH, 1-bromo-3-ethyl-1-methylcyclopropane 1-bromo-2-ethyl-1-methylcyclopropane 1-bromo-1-ethyl-2-methylcyclopropane 2-bromo-1-ethyl-2-methylcyclopropane а. b. с. d. 30. What is the IUPAC name for the following compound? Br CH-CH-CH-C-H а. 3-bromobutanal b. 2-bromobutanal с. 3-bromobutanone d. 2-bromobutanone In order to carry out the following reaction which of the following reagents would be needed? A strong oxidizer followed by water b. а. Water followed by a strong acid A strong acid in an aqueous solution followed by a strong oxidizer A strong oxidizer followed by a strong acid с. d.arrow_forwardWhich of the following cyclohexane conformation is (are) consider to be the most stable conformation for cis-1,2-dimethylhexane? II III I I only В. П only C. III only D. I, II, and IIIarrow_forward6. Consider the structure of cis-1,2-dimethylcyclopropane and trans-1,2-dimethylcyclopropane A. Which compound is more stable? Explain. B. Which compound will release more heat upon combustion? Explain C. Based on the following interactions, predict the difference in energy between the cis and trans isomers. Each CH3 Each CH3 Each H Each H CH3 gauche interaction is worth 0.9 kcal/mol CH3 eclipsed interaction is worth 2.6 kcal/mol CH3 eclipsed interaction is worth 1.4 kcal/mol H eclipsed interaction is worth 1.0 kcal/molarrow_forward
- Considering rotation around the indicated bond in each compound, draw Newman projections for the most stable and least stable conformations. a. CH3-CH2CH2CH2CH3 b. CH;CH,CH2-CH,CH2CH3arrow_forwardConsider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forwardGiven the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C, B H. How is Compound B related to the chair conformation? O It is a conformation isomer (conformer). H3C H3C H O It is a constitutional isomer. O It is not an isomer. H. O It is a stereoisomer.arrow_forward
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