Concept explainers
(a)
Interpretation:
The potential energy versus dihedral angle for
Concept introduction:
Newman projection is a way of representing the groups attached to carbon atoms in the
The energy of the conformers varies with change in their dihedral angle. The plot of this variation is known as potential energy curve.
(b)
Interpretation:
The conformer present in highest amount in a sample of
Concept introduction:
Newman projection is a way of representing the groups attached to carbon atoms in the
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EBK ORGANIC CHEMISTRY
- What is the most stable conformation for trans-1,2-dichlorocyclohexane. Describe and explain brieflyarrow_forwardDraw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.arrow_forwardGiven that the free energy of the twist-boat conformer of cyclohexane is 5.3 kcal/mol greater than that of the chair conformer, calculate the percentage of twist-boat conformers present in a sample of cyclohexane at 25 °C.arrow_forward
- Define Cyclopropanation ?arrow_forwardShow that the addition of each CH2 unit to an alcohol molecule changes the heat of combustion by: 2(C-H)+1(C-C)+1.5(O=O) – [2(C=O)+2(O-H)]arrow_forwardGibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4. (a) Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25C. (b) Explain why the conformational equilibria for methyl, ethyl, and isopropyl substituents are comparable but the conformational equilibrium for tert-butylcyclohexane lies considerably farther toward the equatorial conformation.arrow_forward
- 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Which of the alternative chair conformations of lindane is more stable? Explain.arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Draw a chair conformation for lindane and label which chlorine atoms are axial and which are equatorial.arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Draw the alternative chair conformation of lindane and again label which chlorine atoms are axial and which are equatorial.arrow_forward
- 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Using a planar hexagon representation for the cyclohexane ring, draw a structural formula for lindane.arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Draw a structural formula for 1,2,3,4,5,6-hexachlorocyclohexane disregarding, for the moment, the existence of cis,trans isomerism. What is the molecular formula of this compound?arrow_forwardDraw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997) Provide a reason for your choice by identifying all of the interactions that led to your decision. H₂C OH C₂ HO CH3 Which of the following is the most stable staggered conformer? Me Me *** Conformer B Me- Me Conformer A Me Conformer C Me Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning