Concept explainers
Interpretation:
The Newman projections of
Concept introduction:
Newman projections are used to show the relative positions of the groups attached to the two carbon atoms of the bond of interest. The representation is drawn looking along the bond. The carbon in front is represented by a point, while the carbon at the back is represented by a concentric circle. The bonds to the three groups on the front carbon converge on the point. Bonds to the three groups on the back carbon end on the circle. Depending on the dihedral angles, the conformers are classified as eclipsed or staggered with angles of
Depending on the relative positions of the bulkiest groups on the front and back carbon, the staggered conformers are further divided into anti and gauche. In anti-conformers, the bulkiest groups on the front and back carbons are directly across from each other with a
A molecule possesses a plane of symmetry if a plane passing through its center divides it into halves that are mirror images of each other.
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ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
- Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.arrow_forwardmyo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.arrow_forwardOn the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25). (a) Convert the stereorepresentation on the left to a planar hexagon representation. (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?arrow_forward
- Draw the conformational analysis of 1-bromobutane looking at the C1-C2 bond. Provide the appropriate names for each conformation.arrow_forwardOf all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?arrow_forwardDraw the Newmann projections of this molecule along the circled bond of this molecule, from the point of view of the eye. You should include and label the syn-periplanar, gauche, anticlinal and anti-periplanar conformations, and whether the conformation is staggered or eclipsed. List these four conformations from most stable to least stable?arrow_forward
- how to calculate the percentage of axial and exuatorial in conformation in organic chemistryarrow_forwardcalculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?arrow_forwardConverting a Hexagon with Substituents to a Chair Form Draw the two chair forms for the following trisubstituted cyclohexane, and label the more stable conformation.arrow_forward
- According to the following structure, draw the Newmann projections in which you must indicate: a) the most stable conformation and explain why it is more stable, b) the least stable conformation and explain why; c) a conformation where there is a gauche interaction.arrow_forwardIllustrate a Newmann projection for the most stable conformation of the following molecule looking down the C3-C4 bondarrow_forwardWhat is the potential energy of a conformation?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning