Interpretation:
The
Concept introduction:
The anti and gauche bonds in cyclohexane are represented by sawhorse projections of staggered conformations of
The substituents in anti-relationship are
The substituents in gauche relationship are
In the following structure, each path shows anti relationship where a substituent is equatorial.
In the following structure, each path shows gauche relationship where a substituent is axial.
The torsion (dihedral) angle for eclipsed conformation is
The torsion (dihedral) angle for gauche conformation is
The torsion (dihedral) angle for anti-conformation is
Want to see the full answer?
Check out a sample textbook solutionChapter 3 Solutions
Organic Chemistry - Standalone book
- Tell whether the following pairs of compounds are identical, constitutional isomers, stereoisomers, or unrelated. (a) cis-1, 3-Dibromocyclohexane and trans-1, 4-dibromocyclohexane (b) 2, 3-Dimethylhexane and 2, 3, 3-trimethy1pentanearrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forwardIdentify each substituent in the following compound as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green = Cl):arrow_forward
- Me 11 H 7 H Et H a) If a substituent is placed at C-11 in the equatorial position, is this substituent cis or trans to the methyl group? b) If a substituent is placed at C-7 in the axial position, is this substituent cis or trans to the ethyl group? c) If a substituent is placed at C-1 trans to the methyl group, is this substituent axial equatorial?arrow_forwardDraw the most stable structure of cis-1-tbutyl-2-methylcyclohexane. Your structure should clearly distinguish between axial and equatorial positions.arrow_forwardIn which chair conformation (a or b) is the methyl group farthest from the neighboring hydrogen atom? In which chair conformation (a or b) does the methyl group have greater room? Which is the preferred conformation of methylcyclohexane (a or b)?arrow_forward
- Draw Newman projections for staggered and eclipsed conformations formed by rotation about C2 – C3 bond for the following compounds.arrow_forward1. Name compounds by IUPAC nomenclature CH₂CH-COOH a ОН 2) Find all of the heterofunctional compounds among following: ОН 2 сн, -ен, -с NH, OH COOH CH-OH CH,COOH e b COOH H-C-OH н-с- -ОН COOH -СООН f с H₂C-C-CH₂ 0 COOH HO-C-CH,COOH CH,COOH CH2-CH-CH2; OH ОН ОН g d ОН HOOC–C–CH,COOH ОН HOỌC –COOH б ONaarrow_forwardConsider the molecule shown below. NH2 Он Which of the following statements is true regarding this structure? O In the most stable chair conformer, both the amine and the cyclopentyl substituents would be in the equatorial position. O In the most stable chair conformer, both the amine and the alcohol substituents would be in the equatorial position. O The most stable chair conformer has no steric strain. O The cyclopentane ring is planar. O The alcohol substituent is trans to the amine substituent.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_forwardThe most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its five substituents all in equatorial positions. Draw the most stable conformer of glucose by putting the OH groups and hydrogens on the appropriate bonds in the structure on the right.arrow_forwardAssume that you have a variety of cyclohexanes substituted in the positions indicated. Identify the substituents as either axial or equatorial. For example, a 1,2-cis relationship means that one substituent must be axial and one equatorial, whereas a 1,2-trans relationship means that either both substituents are axial or both are equatorial. a) 1,4-cis-disubstituted b) 1,6-cis-disubstituted c) 1,2-cis-disubstituted Submit Answer Try Another Version 6 item attempts remaining optioins fill please both axial only both equatorial only both axial or both equatorial one axial-one equatorialarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning