Concept explainers
Interpretation:
The given model of half chair conformation is to be examined from different points of view, and the different types of strains are to be noted. The site of strain and the types of strain are to be indicated. Why the half-chair conformation is so high in energy is to be justified.
Concept introduction:
Cyclohexane has no ring strain because it adopts a chair conformation in which all angles are about
The half-chair conformation in a chair flip is higher in energy than the chair conformation itself due to added ring strain.
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Chapter 4 Solutions
ORGANIC CHEMISTRY PRINCIPLES & MECHANISM
- Draw the “chair twist" of the following molecules. Label the more stable conformation. Br •CH3 OH Draw planar models of the above molecules. Draw both chair conformation of the following molecule, and identify the most stable form. Me Me ....Et Mearrow_forwardStarting with the chair conformer shown on the left, provide a potential energy plot for the chair-to-chair flip of that conformer. Label each of conformers by name. Present appropriate relative energies by the positioning of each conformer on your plot, assuming that all of the isotopes of hydrogen are the same size. T Darrow_forwardFor every structure below, draw the most stable chair conformation. Where two or more conformations are equally stable, draw both.arrow_forward
- 3)- Determine the total number of conformers and draw the Chair Structures of the conformers for the Tri-substituted cyclohexane structure given below (i.e., "A"). Draw the relative energy diagram for the possible conformers for the cyclohexane structure below. Note, draw only the required structures for the conformers of A. Also, include hydrogen atoms wherever there are substituents on all of your chair conformers. Answer (Total #of Conformers): Chair Structures: Relative Energy Diagram 8 bas roll 3arrow_forward[Review Topics] [References) Use the References to access important values if needed for this question. a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below. b. Specify substituent positions (axial or equatorial) in the more stable chair. c. Estimate the percent of the more stable chair at equilibrium at 25°C. (To determine the percent of the more stable chair at equilibrium, first calculate K, and then use this value to find the percentage.) он (in isopropanol) Answers: kJ/mol. a. The energy difference is b. In the more stable chair: • The hydroxyl group is in the | • The chloro group is in the | c. At 25°C the equilibrium percent of the more stable chair conformation is approximately | position. |position. An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer. Submit Answer Retry…arrow_forward2. Draw the flipped chair conformation of a. Which of the two conformations is more stable? Justify your answer. #s S.arrow_forward
- Paraphrasing ewriting Tool Car note Pirate Ship BLACKBOARD wos 6Baun paumn [Review Topics) [References) Use the References to access important values needed for this question. a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below. b. Specify substituent positions (axial or equatorial) in the more stable chair. c. Estimate the percent of the more stable chair at equilibrium at 25°C. (To determine the percent of the more stable chair at equilibrium, first calculate Ke and then use this value to find the percentage.) OH (in isopropanol) Answers: a. The energy difference is b. In the more stable chair: kJ/mol. o The methyl group is in the o The hydroxyl group is in the e position. 8 position. c. At 25°C the equilibrium percent of the more stable chair conformation is approximately Submit Answer Retry Entire Group 9 more group attempts remaining…arrow_forward4. Clearly draw both Chair Conformations. of the following molecule Xordin 5. for the Molecule in Question 4 - Circle the lowest energy Chair Conformat. TAM!arrow_forwardConsider the pair of compounds shown below then select the word or phrase that best describes the relationship between them.. Me H OH H Me OH and H OH Me Me They are diastereoisomers, but differ in their conformations. O They are constitutional isomers that, by definition, differ in their conformations. None of these are accurate. They are identical, but differ in their conformations. O They are enantiomers, but differ in their conformations.arrow_forward
- [Review Topics] [References] Specify the types of strain that destabilize the conformer shown below. Hint: All bonds not explicitly shown are in the staggered conformation. 1. Torsional strain 2. Angle (ring) strain 3. Steric (van der Waals) strain [ H3C H3C H CH3 CH3 ball & stick- + labels CH₂arrow_forward[Review Topics] (References) Use the References to access important values if needed for this question. a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below. b. Specify substituent positions (axial or equatorial) in the more stable chair. c. Estimate the percent of the more stable chair at equilibrium at 25°C. (To determine the percent of the more stable chair at equilibrium, first calculate Keg and then use this value to find the percentage.) OH H₂C (in isopropanol) Answers: a. The energy difference is b. In the more stable chair: kJ/mol. The methyl group is in the The hydroxyl group is in the [ position. position. c. At 25°C the equilibrium percent of the more stable chair conformation is approximately Submit Answer Retry Entire Group 1 more group attempt remaining Show Hint Previous Save and Exitarrow_forwardHow do you account for the difference in energies between the two staggered conformations of 1,2-dichloroethane? How about for the two eclipsed conformations? Draw all four conformations and, on your drawing, indicate sources of strain – torsional, steric (gauche), steric eclipsed.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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