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For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring and wedges and dashed wedges for substituents.
b. Draw the two possible cahir 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?
[1] [2]
[3]
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Chapter 4 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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- Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.arrow_forwardLabel each ring in Figure 7.2 cis or trans.arrow_forwardIn the next chapter we'll look at cycloalkanes—saturated cyclic hydrocarbons—and we’ll see that the molecules generally adopt puckered, nonplanar conformations. Cyclohexane, for instance, has a puckered shape like a lounge chair rather than a flat shape. Why?arrow_forward
- For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. 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? [1] [2] [3]arrow_forwardWhich is more stable and why? II A. I because it has a chair conformation with the most axial bonds B. I because it has a chair conformation with the most equatorial bonds C. II because it has a chair conformation with the most axial bonds OD. II because it has a chair conformation with the most equatorial bonds %3Darrow_forwardMonosubstituted cyclohexanes occur in two equilibrium conformations. In one conformation, the substituent is in an axial position. In the other conformation, the substituent is in the equatorial position. Complete the drawing of each chair conformation below and circle the more stable conformation. Brarrow_forward
- For 1,2-dichloroethane: a.Draw Newman projections for all eclipsed conformations formed by rotation from 0° to 360° about the carbon-carbon single bond. b.Which eclipsed conformation(s) has (have) the lowest energy? Which has (have) the highest energy? c.Which, if any, of these eclipsed conformations are related by reflection?arrow_forwardFor each attached compound drawn below:a.) Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.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_forwardNonearrow_forward
- Draw the following molecules in their most stable conformation. You do not have to draw the least stable conformation, unless you find it helpful practice.arrow_forwardrotation here a. Draw the three staggered and three eclipsed conformations that result from rotation around the designated bond using Newman projections. b. Label the most stable and least stable conformation. CH3-C-CH,CH3arrow_forward4. Draw the Newman projection of the conformer below as it is drawn looking down the indicated C-C bond. Then draw the most stable conformer and the least stable conformer as Newman projections. PH. CH3 H H CI Newman of Drawn Newman of Most Newman of Least Conformer Stable Conformer Stable Conformerarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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