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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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Chapter 4 Solutions
EBK ORGANIC CHEMISTRY
- Write 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_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 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_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_forward
- Draw 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_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_forwardHello, 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_forward
- Draw 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_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_forwardThe skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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