Videos
(a)
Interpretation:
The Newmann projection and sawhorse conformations of the given line-and-wedge structure are to be drawn.
Concept introduction:
Newmann projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
(b)
Interpretation:
The line-and-wedge and sawhorse conformations of the Newmann projection of (a) by rotating
Concept introduction:
Newmann projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
(c)
Interpretation:
The line-and-wedge and sawhorse conformations of the Newmann projection of (a) by rotating
Concept introduction:
Newmann projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
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Chapter 2 Solutions
Organic Chemistry
- C6H12 From the chair conformation, rotate about the carbon-carbon bonds of the ring to form a boat conformation. In the boat conformation carbon atoms 1 and 4 are both above (they could also both be below) the plane described by carbon atoms 2, 3, 5 and 6. Look through each of the C-C bonds in the cyclohexane ring. Do you observe any eclipsing interactions? If so, describe what atoms/substituents are eclipsing.arrow_forwardconstruct a qualitative potential-energy diagram for rotation about the c-c bond of 1,2 -dibromoethane. which conformation would you expect to be most stable? label the anti and gauche conformations of 1,2-dibromoethane.arrow_forwardDraw the most stable conformer of trans-1-t-butyl-3-methylcyclohexane. the structure should clearly distinguish between axial and equatorial positionsarrow_forward
- Looking at C1 with C2 behind C1, complete the Newman Projection diagrams. The angles are defined as the dihedral angle between C1-Br and C2-F. 0° 60° 120° 180° Complete the following potential energy diagram by plotting relative energy of each of the above Newman Projections is versus dihedral angle. The plot should show the correct relative order of the potential energy of each conformation.arrow_forwardFor 1-bromobutane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.arrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model. (See attached) Label the substituents on C1, C2, and C4 as axial or equatorial.arrow_forward
- Draw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997) Provide a reason for your choice by identifying all of the interactions that led to your decision. H₂C OH C₂ HO CH3 Which of the following is the most stable staggered conformer? Me Me *** Conformer B Me- Me Conformer A Me Conformer C Me Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.arrow_forwardMake a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity. 1,2-dichloropropanearrow_forwardStarting from the Newman projection below, rotate the back carbon to provide the structure in the most stable conformation. H H3C H H -CH(CH3)2 H Drawing earrow_forward
- Draw Newman projections, in order of decreasing energy, for all staggered conformations of 1,2- dibromooethane formed by rotation of the carbon-carbon bond from 0° to 180°.arrow_forwardConstruct a qualitative potential energy diagram for rotation about C-C bond of 1,2-dibromoethan. Which conformation would you expect to be more stable? label the anti and gauche conformation of 1,2-dibromoethanearrow_forwardFor each of the following molecules, draw the planar line-angle drawing, using wedges and dashes to show stereochemistry. Then, draw both alternative chair conformations. Circle which chair conformation is favored; if the two chair conformations are equal in energy, circle both.. cis-1,3-diethylcyclohexane cis-1,2-dimethylcyclohexane (1S, 3S)-1-(tert-butyl)-3-methylcyclohexanearrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning