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 Chemistry
- Rank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable.To rank items as equivalent, overlap them.arrow_forwardWrite the energy diagram corresponding to each conformer by writing the conformers (and Newman projection formulas) formed by the rotation of the bond between the carbon 3 and 4 (C3 and C4) of the 2-methylpentane. Indicate the most stable and unstable conformers.arrow_forwardFollowing 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_forward
- For 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_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw Newman projections for the conformations in which -CH3 and -Br are gauche (dihedral angles 60° and 300°).arrow_forwardA 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_forward
- Draw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forwardDraw 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_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 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_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