ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 4.9, Problem 15P
Interpretation Introduction
Interpretation: The possible Newman projections for
Concept introduction: Newman projections are drawn to visualize the different conformations of a compound around
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6. Newman projections to Lewis structures
From the following Newman projections, draw the corresponding Lewis
structure in the same conformation.
A)
B)
H.
H
CH3
H₂C N
H
OH
CI
Br
CH3
H
OH
CH3
(a) Draw the Newman projection for each molecule
shown here, looking down the C-C bond indicated
by the arrow. (b) Which configuration do you think is
more stable? Explain.
H3C'
*CH3
H3C
'CH3
cis-1,2-Dimethylcyclopropane
trans-1,2-Dimethylcyclopropane
Chapter 4 Solutions
ORGANIC CHEMISTRY
Ch. 4.1 - Prob. 1PCh. 4.1 - Problem 4.2 Which of the following is not another...Ch. 4.1 - Problem 4.3 Draw the five constitutional isomers...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.2 - Draw the five constitutional isomers that have...Ch. 4.4 - Problem 4.7 Give the IUPAC name for each...Ch. 4.4 - Give the IUPAC name for each compound. a....Ch. 4.4 - Problem 4.9 Give the structure corresponding to...Ch. 4.4 - Prob. 10P
Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- organic chemistryarrow_forward2) a) Provide Newman projects of the three staggered conformations of molecule 1 shown below looking down the indicated bond (1→2). Circle the most stable conformation. HH3C CH3 H molecule 1 b) Provide Newman projects of the three eclipsed conformations of molecule 1 looking down the indicated bond. Put a square around the least stable conformation.arrow_forwardHydrocarbon X below has the following Newman projection. Which of the following corresponds to Hydrocarbon X? O 2,3-dimethylhexane O 2,4-dimethylpentane O 2,4-dimethylhexane O 2,3-dimethylpentane O n-heptane H3C a DH H CH3 CH₂CH3 H3Carrow_forward
- H C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. b) Which staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy which has the highest energy?arrow_forwardComplete the following Newman projection so that it represents (2R,3S)-2,3-butanediol.arrow_forwardDraw a dash-wedge structure for (1R)-1-bromo-1,3,3-trimethylcyclohexane.arrow_forward
- Consider rotation about the indicated bond in the molecule below. Which Newman Projection formula best represents the most stable conformer of the molecule with respect to rotation about the indicated bond? [As noted below: there is no steric strain between -H and -Et that have a gauche, staggered relationship] H CH3 Br-C-C-CH₂CH3 H. H Br CH₂CH₂ 1 CH3 H CH3CH₂ H Br H₂C || H H₂C H Br H ||| Select one: OA. I O B. II O C. III O D. All conformers have identical energies. CH₂CH3 H NOTE CH3CH₂ H no steric strainarrow_forward4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane. (b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the carbon-3 to carbon-4 bond. (c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation that you drew as a sawhorse representation.arrow_forwardQuestion: A Newman Projection of a tetrahydropyran is drawn below. Draw a bond line-angle representation of the substituted tetrahydropyran in the following figure. Be sure to show realtive positions in the bond-line structure by using either dashes or wedges.arrow_forward
- translate the bond-line notation structure to the Newman projection by filling int the missing groups (A, B, C, D or E) on the lines in the Newman projection so they match the conformation given in the original structure. Circle if the conformation is a staggered or eclipsed.arrow_forward. Draw the two most stable Newman projections of 3-methylpentane by viewing along the C2-C3 bond.arrow_forward3. Draw Newman projection for the highest and lowest energy conformers of your assigned molecule. Provide a rationale to support your answer. In other words, why is the highest energy conformer so high in energy? Why is the lowest energy conformer low in energy? Molecule (2R,3S)-2-Bromo-3- Floro butanearrow_forward
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