Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 24VC
A trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip to its alternate chair conformation. Identify each substituent as axial or equatorial, and show the positions occupied by the three substituents in the ring-flipped form.
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Chapter 4 Solutions
Organic Chemistry
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- Draw the substituents in the specified locations on the given cyclohexane ring to show the most stable chair conformation. Be sure that the bonds are drawn to clearly show whether they are axial or equatorial. CH₂ 1 Substituent Position Br 5 3 5 3 Q C C с X ㅃ E Jh Cx C 00 olo Ar 18 Karrow_forwardDraw the four possible positions, the cis and trans positions of the methyl groups for both the chair and boat conformations, of 1,4-dimethylcyclohexane. Label each as cis or trans and identify the highest in energy.arrow_forwardConsider the isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert-butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four conformations is the most stable. FIX a box OH HO OH A Select the more stable conformation of cis-2-tert-butylcyclohexanol. B OD C B C D ☐A C OH Select the more stable conformation of cis-3-tert-butylcyclohexanol.arrow_forward
- Identify the cyclohexane chair conformation with an axial ethyl substituent and equatorial methyl group. OL O II III O IV C > ။ IVarrow_forwardComplete the given chair conformation of cyclohexane by adding the listed substituents to the specified position and bond direction. Substituent Position Bond direction CH3 CH3 OH F 3 6 1 3 axial axial equatorial equatorialarrow_forwardConformational studies on ethane-1,2-diol (HOCH2¬CH2OH) have shown the most stable conformation about the central C¬C bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers, and explain this curious result.arrow_forward
- Draw the substituents in the specified locations on the given cyclohexane ring to show the most stable chair conformation. Be sure that the bonds are drawn to clearly show whether they are axial or equatorial. Substituent Position OH 1 OH 3 F 4 CH, 5arrow_forward9arrow_forwardStarting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H3C H Br H H3C H Qarrow_forward
- Draw a Newman projection for two more staggered conformations of this molecule. Which of your conformations is most stable? Assume that -OH and -CH3 are comparable in size.arrow_forwardDraw alternative chair conformations for the following substituted cyclohexane and determine which chair is more stable. C HO H ОН In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:arrow_forwardPick the correct statement describing the following substituted cyclohexane conformation shown: CH3 .CI HỎ O All of the groups (OH-group, Cl-atom, and CH3-group) have a trans relationship. O The OH-group and the Cl-atom have a cis relationship, while the CH3-group and the Cl-atom have a trans relationship The OH-group and the Cl-atom have a trans relationship, while the CH3-group and the Cl-atom have a cis relationship O All of the groups (OH-group, Cl-atom, and CH3-group) have a cis relationship.arrow_forward
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