Using 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.

Using 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.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter26: Lipids

Section: Chapter Questions

Problem 26.24P: Following is a structural formula for cortisol (hydrocortisone). Draw a stereo-representation of...

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Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

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Following is a structural formula for cortisol (hydrocortisone). Draw a stereo-representation of this molecule showing the conformations of the five- and six-membered rings.
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.
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?
Consider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered 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?
Answer the following questions and upload your answer. A. Draw the two chair conformations of cis-1-isopropyl-3-methylcyclohexane. Write under your drawing which conformation is the most stable one. B. Would the trans isomer be more stable than the cis isomer? Why?
4. 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 I
Analyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.
3. Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).
1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman projection and the chair drawing. Calculate the energies of each. What ratio of the two conformers will be present at equilibrium? 2. Draw a structure of a chiral alcohol.
1,2-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.
Consider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc. a.Which conformer is the most stable? the least stable? b.Which rotamer is the anticonformer? the gaucheconformer? c.Draw the anticonformer in saw horse projection.
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