Interpretation:
The reason for more stability of gauche conformation of ethylene glycol as compared to butane is to be explained.
Concept introduction:
Staggered conformation: It is the arrangement of atoms or groups of atoms in a molecule, resulting in a
Anti-co-planer conformation: It is the arrangement of atoms or groups of atoms in a molecule, resulting in a 1800 dihedral angle between two largest groups. It is also called anti-staggered or anti-conformation. It has low potential energy because of less torsional strain, and hence, more stable.
Eclipsed conformation: It is the arrangement of atoms or groups of atoms in a molecule, resulting in a
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Organic Chemistry
- calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?arrow_forwardWhen you obtained a geometry optimized structure of methyleyelopentane, did you determine the energy of the most stable conformation? Why or why not?arrow_forwardFor each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) 1-bromopropane or cyclopropanearrow_forward
- Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.arrow_forwardHow many isomers would you expect for each of 1-chloro-2-hydroxycyclohexane, 1- chloro-3-bromocyclohexane and 1,3- dimethylcyclohexane; differentiate between geometrical and optical isomers where appropriate.arrow_forwardBetween the cis and trans configuration of 1-chloro-4-methylcyclohexane, which is the most stable stereoisomer and configuration? To prove your argument, draw a model or use a modeling software to model cis- and trans-1-chloro-4-methylcyclohexane (show all the hydrogens and ensure proper chair conformation) and use arrows to show where steric strain occurs.arrow_forward
- Why is the percentage of molecules with the substituent in an equatorial position greater for isopropylcyclohexane than for fluorocyclohexane?arrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of cis-1,2-dimethylcyclobutane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forwardCompare the relative conformational energydiagrams of ethane and propane.arrow_forward
- Sketch a potential energy diagram for rotation around a carbon–carbon bond in propane. Identify each potential energy maximum and minimum with a structural formula that shows the conformation of propane at that point. Does your diagram more closely resemble that of ethane or of butane? Would you expect the activation energy for bond rotation in propane to be more than or less than that of ethane? Of butane?arrow_forwardWhich of the following two conformations of trans-3-methylcyclohexanol is more stable? Use the strain energy increments in the table below estimate the energy difference (a positive number) between them.arrow_forwardThe anti-conformation is the most stable n-butane conformation. If you could take a snapshot of a mole of n-butane, would a sizeable number of the molecules be in the gauche-conformation? Why or why not?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning