Concept explainers
Interpretation:
Using Newman projection, the relative positions of the substituents on the bridgehead atoms of cis- and trans- decalin is to be depicted and the isomer which is more stable is to be determined and the reason for the same is to be explained..
Concept introduction:
Newman projected two types of spatial arrangements of molecules which are staggered and eclipsed Newman projections.
Staggered conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a
Eclipsed conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a
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ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- 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.arrow_forwardDraw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forwardFor rotation about the C-a – C-b bond, using the following templates, draw the Newman Projection of the two staggered conformers that are different in energy. Fill each bond on Newman Projection with Hydrogen or Substituents. You may use Abbreviations such as Me for Methyl, Et for Ethyl, iPr for isopropyl. Circle the Newman projection of the most stable conformer.arrow_forward
- A structure with the formula C7H14O must be drawn that contains one stereocenter, an alcohol, and a disubstituted alkene including what the IUPAC name is for this compound. Dashes/wedges should be used to show which enantiomer is being drawn. In addition, what is the enantiomer drawing and IUPAC name of this compound, as well as the diastereomer of this compound and IUPAC name?arrow_forwardDraw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw Newman projections for the conformations in which -CH3 and -Br are gauche (dihedral angles 60° and 300°).arrow_forward
- Draw all the possible conformations of trans- and cis-1,3-dimethylcyclobutane. Which of these conformations is the most stable conformation? Explain your answer. Discuss the type of strain(s) that affect the stability of these compounds.arrow_forwardDraw a structural formula for cis-1-bromo-3-ethylcyclopentane. • Show stereochemistry only if given in the name. • In cases where there is more than one answer, just draw one.arrow_forwardThe energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forward
- Hello, I was reading an answer from the book Organic Chemistry by Brown et al. The question is 2.51 "Draw alternative chair conformations for each substituted cyclohexane and state which chair is more stable." There are then 4 cyclohexanes (labeled a-d). For the "a" cyclohexane, the substituents are arranged as a combination of axial and equatorial in both chair conformations. However, for the "b," "c," and "d," cyclohexanes one chair has only equatorial substituents, and the other chair has only axial substituents. Why is the "a" chair conformation different? https://www.bartleby.com/solution-answer/chapter-2-problem-251p-organic-chemistry-8th-edition/9781305580350/draw-alternative-chair-conformations-for-each-substituted-cyclohexane-and-state-which-chair-is-more/4532cd91-c341-11e9-8385-02ee952b546earrow_forwardDraw Newman projections for the anti, eclipsed, gauche and fully eclipsed conformations of Butane. Indicate their relative stabilities and the reasons for your ranking-need to discuss the stresses involved in each case. Using suitable specific conformers of specific structures as examples, explain the difference between (a) angle strain (b) torsional strain and (c) steric strain. Need to draw the confomers and structures 4) Draw the most stable conformers using chair structures of the following: (c) cis-1,2-Dibromocyclohexane (d) trans-1,2-Dibromocyclohexane (e) cis-Decalin (f) trans-Decalin . Draw the most stable conformers of trans-1-Bromo-4-methylcyclohexane and cis-1-Bromo-4-methylcyclohexane. Which is more stable? Explain the reason for your answer. Need to include a discussion of 1,3-Diaxial interactionarrow_forwardWhich of the following is an incorrect statement: Isomers have the same molecular formula such as cyclohexane and 1-hexene. Conformational isomers are enantiomers or diastereomers, which can interconvert through rotations around bonds within molecules, which include anti and gauche butane. Stereoisomers have the same connectivity but different arrangement of their parts in space, which include enantiomers, diastereomer, and conformational isomers, which include cis and trans dichlorocyclobutane. O Structural or constitutional isomers are molecules of the same formula but different connectivity such as 1,1-dichlorocyclopropane and 1.2-dichlorocyclobutane.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning