Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Question
Chapter 4, Problem 4.15P
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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(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
Draw the skeletal structure of a neutral acyclic molecule with one tetrahedral stereocenter. You may use only 8 carbon atoms and 1 halogen atom, plus as
many hydrogen atoms as you like.
Click and drag to start drawing
a structure.
S
Shm
C
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
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...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 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 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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- Which of the attached is (are) possible Newman projections for 2-methylpentane?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_forwardWhich of the following is (are) possible Newman projections for 2-methylpentane?arrow_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_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_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_forwardThen draw the most stable and least stable Newman projection conformation from the C4-C5 bond in the molecule abovearrow_forwardDraw the highest and lowest energy Newman projection for 2- bromo-2,3-dimethylpentane when looking down C1-C2, C2-C3, C3-C4, C4-C5 bonds.arrow_forward
- Sight along the C2 - C; bond of 2,3 -dimethylbutane, and draw a Newman projections for all the staggered and eclipsed conformation. Draw the expected potential energy diagram for this molecule. 2 3 4 ĈH3-CH2 – CH – CH3 CH3 CH3 2, 3 - dimethyl butanearrow_forwardtranslate 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_forward
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