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(a)
Interpretation:
Both the chair conformations for cis-1,2-dimethylcyclohexane is to be drawn and the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:
The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(b)
Interpretation:Both the chair conformations for trans-1,2-dimethylcyclohexane is to be drawn and should identify the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(c)
Interpretation:Both the chair conformations for cis-1,3-dimethylcyclohexane are to be drawn and the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(d)
Interpretation:Both the chair conformations for trans-1,3-dimethylcyclohexane are to be drawn andthe compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
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Chapter 4 Solutions
Organic Chemistry: Structure and Function
- Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forwardFollowing is the Structural formal of Chloropropane H H H 2. H Draw Newman projections for all staggered and eclipsed conformation formed by rotation about C1 - C2 bond from 0° to 360°. b) Which Staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest energy?arrow_forward3)) Draw the most stable chair conformation of a 1,2,4-trimethylcyclohexane (Show all the hydrogens and indicate if the bond is axial or equatorial at the substitution).arrow_forward
- There are four cis,trans isomers of 2-isopropyl-5-methylcyclohexanol:(a) Using a planar hexagon representation for the cyclohexane ring, draw structural formulas for the four cis,trans isomers.(b) Draw the more stable chair conformation for each of your answers in part (a).(c) Of the four cis,trans isomers, which is most stable? (Hint: If you answered thispart correctly, you picked the isomer found in nature and given the name menthol.)arrow_forwardH C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. b) Which staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy which has the highest energy?arrow_forwardWhich are the correct conformations of 2,2-dimethylpentane?arrow_forward
- (a) Draw the most stable chair conformers of trans-1,3-diisopropylcyclohexane and trans-1,4-diisopropylcyclohexane. (b) Which is more stable: trans-1,3-diisopropylcyclohexane or trans-1,4-diisopropylcyclohexane?arrow_forwardDraw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3- dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a ) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?arrow_forwardAcetylcholine is a neurotransmitter in the central nervous system in humans. Sighting along the C-C bond, draw Newman projection formulas for all the eclipsed and staggered conformers of acetylcholine. Which among the conformers is the least stable? The most stable? Plot a conformational analysis for these conformers.arrow_forward
- ' Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane 1,3-dimethylcyclohexane, and 1,4-dimethylcyclohexanearrow_forwardIndicate the relationship between the two structures in the pair. Are they chair conformations of the same molecule? If so, are they conformational diastereomers, conformational enantiomers, or identical? If they are not conformations of the same molecule, what is their stereochemical relationship? CH₂ CH₂ H₂C H₂C CH₂ Which statement is true? Ho CH₂ They are chair conformations of the same molecule, and they are conformational enantiomers. They are different molecules, and they are enantiomers. They are different molecules, and they are diastereomers. They are identical conformations of the same molecule. They are chair conformations of the same molecule, and they are conformational diastereomers.arrow_forwardDraw both chair conformations of cis-1,2-dimethylcyclohexane, and determine which conformer is more stable.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning