Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3.7C, Problem 3.12P
Draw a graph similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.
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Check out a sample textbook solutionStudents have asked these similar questions
a) Draw all Newman projections
of your molecule's conformations
in which the CH3 group and the
H of the CHY2 group are
positioned 'ANTI' to each other.
Be sure to put in the correct X
and Y atoms, bonded to the
correct C atoms, for your
molecule. X = FY=I
Conformations = 60 deg and
-
180 deg 60 deg dihedral angle
= - 179.987 deg 180 deg ·
-
dihedral angle
=
179.814 deg
Starting from the wedge-and-dash structure below, rotate the
back carbon to provide the Newman projection in the most
stable conformation.
I
1
H3C
H"
H3C
Drawing
>
H
Br
H
Starting from the wedge-and-dash structure below, rotate the
back carbon to provide the Newman projection in the most
stable conformation.
H3C
H
H3C
H
Br
H
Chapter 3 Solutions
Organic Chemistry (9th Edition)
Ch. 3.2 - Using the general molecular formula for alkanes:...Ch. 3.3B - Name the following alkanes and haloalkanes. When...Ch. 3.3B - Write structures for the following compounds. a....Ch. 3.3B - Provide IUPAC names for the following compounds....Ch. 3.3B - Prob. 3.5PCh. 3.3B - Prob. 3.6PCh. 3.3B - Prob. 3.7PCh. 3.3B - Draw the structures of the following compounds. a....Ch. 3.3B - Without looking at the structures, give molecular...Ch. 3.4C - Prob. 3.10P
Ch. 3.7B - Prob. 3.11PCh. 3.7C - Draw a graph similar to Figure 3-9, of the...Ch. 3.8B - Draw a graph similar to Figure 3-11, of the...Ch. 3.9 - Draw a perspective representation of the most...Ch. 3.10C - Give IUPAC names for the following compounds.Ch. 3.10C - Draw the structure and give the molecular formula...Ch. 3.11 - Which of the following cycloalkanes are capable of...Ch. 3.11 - Give IUPAC names for the following cycloalkanes.Ch. 3.12B - The heat of combustion of...Ch. 3.12C - Prob. 3.20PCh. 3.13B - The cyclohexane chair shown in Figure 3-22 has the...Ch. 3.13B - Draw 1,2,3,4,5,6-hexamethylcyclohexane with all...Ch. 3.14 - Prob. 3.23PCh. 3.14 - Prob. 3.24PCh. 3.14 - Draw the most stable conformation of a....Ch. 3.15 - Prob. 3.26PCh. 3.15 - a. Draw both chair conformations of cis-1...Ch. 3.15 - Prob. 3.28PCh. 3.15A - Draw the two chair conformations of each of the...Ch. 3.15B - Draw the most stable conformation of a....Ch. 3.16A - Name the following compounds.Ch. 3.16B - Prob. 3.32PCh. 3 - Prob. 3.33SPCh. 3 - Prob. 3.34SPCh. 3 - 3-35 a. Draw and name the five cycloalkane...Ch. 3 - Draw the structure that corresponds with each...Ch. 3 - Each of the following descriptions applies to more...Ch. 3 - Write structures for a homologous series of...Ch. 3 - Prob. 3.39SPCh. 3 - Construct a graph, similar to Figure 3-11, of the...Ch. 3 - The following names are all incorrect or...Ch. 3 - In each pair of compounds, which compound has the...Ch. 3 - There are eight different five-carbon alkyl...Ch. 3 - Use a Newman projection about the indicated bond...Ch. 3 - a. Draw the two chair conformations of...Ch. 3 - Draw the two chair conformations of each compound,...Ch. 3 - Using what you know about the conformational...Ch. 3 - Prob. 3.48SPCh. 3 - Draw Newman projections along the C3C4 bond to...Ch. 3 - Prob. 3.50SPCh. 3 - The most stable form of the common sugar glucose...Ch. 3 - This is a Newman projection of a substituted...
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- Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutanearrow_forward< Question 17 of 25 Subm Identify the Newman projection that depicts the eclipsed conformation of butane. CH₂ 11 CH3 A) I B) II C) III D) IV E) V - H H Ø H. I H H CH3 H H CH3 CH3 IV H H H V H3C CH3 D H Ø HY H H CH3 D H I I H c CH3 H- FH CH3arrow_forward3. Draw both chair conformations for the cyclohexane molecule shown below, and circle the most stable conformation (the methyl group is larger than the hydroxyl group). OH H3Carrow_forward
- Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H₂C H (H3C) 3C H H CH3 →arrow_forwarda. For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. ( see image) b.Draw and name the seven constitutional isomers (all contain a ring of some size) for cycloalkane, C6H12.arrow_forwardSight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forward
- Use a Newman projection to show the most stable conformation of 3,4-dimethylhexane as you look down thebond between carbons 2 and 3.arrow_forwardConsider the energy diagram showing the conformational analysis of propane. Select the number that corresponds to the correct conformation. úr H. H energy H 180 HH H CH3 H. ***** H H H CH3 CH3 0 dihedral angle H H HCH3 H H 180 IV HCH3 H H V CH 3arrow_forward1: Draw the chain conformer of... 1a. Cyclohexane, label all the axial and equatorial hydrogens 1b. The most stable conformer of ethylcyclohexane 1c. The most sable conformer of trans-1-tert-butyl-3-methylcyclohexanearrow_forward
- Acetylcholine is a neurotransmitter in the central nervous system in humans. Sighting along the C-C bond, draw Newman projection formulas for all the eclipsed and staggered conformers of acetylcholine. Which among the conformers is the least stable? The most stable? Plot a conformational analysis for these conformers.arrow_forwardIn the space below, redraw n-butane in this elongated conformation. All C atoms should be drawn in the plane of the paper in a zig-zag to represent the geometry displayed by your model kit. The hydrogen atoms should be attached to the carbon atoms via dashed and wedged bonds, as in question 4C above, to illustrate the three-dimensional geometry of the structure.arrow_forwardUsing solid and dashed wedges, draw the structure of (1S, 2S, 4R, 5R)-1,5-dibromo-2,4- dichlorocyclohexane, then draw the most stable conformer.arrow_forward
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