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Concept explainers
(a)
Interpretation:
TThe two possible chair conformations for the cis-1-isopropyl-3-methylcyclohexane should be drawn and named every substituent as axial or equatorial and most stable conformer should be selected.
Concept introduction:
when the cyclohexane ring converts from one chair conformation to another, the equatorial hydrogen atoms are converted into axial hydrogen atoms and vice versa.
When the cyclohexane has one substituent then the conformation which contain the substituent in equatorial position is more stable due to less steric strain with axial hydrogen atoms.
When two substituents are present in the structure, in order to find the more stable conformation can be determined by looking at the groups in the axial position.
When a bulkier group present in the axial position, that conformation get less stable.
In cis conformation, both substituents are in the same side.
(b)
Interpretation:
The two possible chair conformations for the cis-4-tert-butylcyclohexanol should be drawn and named every substituent as axial or equatorial and most stable conformer should be selected.
Concept introduction:
when the cyclohexane ring converts from one chair conformation to another, the equatorial hydrogen atoms are converted into axial hydrogen atoms and vice versa.
When the cyclohexane has one substituent then the conformation which contain the substituent in equatorial position is more stable due to less steric strain with axial hydrogen atoms.
When two substituents are present in the structure, in order to find the more stable conformation can be determined by looking at the groups in the axial position.
When a bulkier group present in the axial position, that conformation get less stable.
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Chapter 26 Solutions
EP GENERAL CHEMISTRY-MOD.MASTERINGCHEM.
- Indicate the position, axial or equatorial, of each of the groups shown when the ring is in its more stable chair conformation H. C OH CH(CH3)2 b a. b. C.arrow_forwardUsing the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. A. From the nine stereoisomers, identify one pair of enantiomers. B. Draw the most stable conformer of the most stable stereoisomer.arrow_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_forward
- a. Using the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. b. From the nine stereoisomers, identify one pair of enantiomers. c. Draw the most stable conformer of the most stable stereoisomer.arrow_forwardWhich of the following statements is not true regarding the conformation of substituted cyclohexanes? O a. the boat conformation of cyclohexane is usually more stable than the chair conformation O b. ring inversion of cyclohexane between two chair conformations takes place via a boat conformation O c. substituted cyclohexanes are destabilized by 1,3-diaxial interactions d. the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energyarrow_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
- Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered 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_forward4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forward1,2-ditert-butylcyclohexane is an interesting case of a conformational study. The cis isomer is more stable than the trans isomer, although the trans isomer presents a conformer with both substituents in equatorial positions. In order to analyze this fact:a. Draw the conformational equilibrium of both compounds. Explain using and drawing the structures why this difference happens (the one described above). b. In the trans isomer, the di-axial conformation is 25.9 kJ / mol more stable than the di-equatorial. Calculate the energy of the di-equatorial conformation.arrow_forward
- Given 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_forwardThere 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 9.6arrow_forward1. Write the IUPAC names for the following structures. Number the carbons and circle the substituents clearly. Use a pencil to complete this assignment. CH3 a. CH3 - CH2 - CH2 - C- CH2- CH2 - CH3 CH3 CH2-CH3 NAME: CH3 - CH - CH2 - CH2 - CH - C=CH CH2-CH2-CH3 CH3 NAME: C. CH3-CH2 CH2-CH3 EC = c CH3-CH2 CH2-CH2-CH3 NAME: b.arrow_forward
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