Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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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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Students 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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CNarrow_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< 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_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_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_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_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
- 4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forwardAcetylcholine 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_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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