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, Problem 3.44SP
Use a Newman projection about the indicated bond to draw the most stable conformer for each compound.
- a. 3-methylpentane about the C2—C3 bond
- b. 3,3-dimethylhexane about the C3—C4 bond
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Which projection corresponds to 2,3,4-trimethylhexane?
CH,CH3
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CH(CH3)2
ČH3
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CH,CH3
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(CH3)2CH
CH3
H3C,
C.
HY CH;CH(CH3)2
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CH3
d.
(CH3),CH,
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Y CH,CH3
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a.
What is the preferred IUPAC name of the
alkene shown in Figure below?
CH3
CH3
CH3
`CH-CH3
A. 1-ethyl-2,4,5-trimethylcyclohexene
B. 2-ethyl-1,4,5-trimethylcyclohexene
C. 2-ethyl-1,4,5-trimethylcyclohex-1-ene
D. 4-ethyl-1,2,5-trimethylcyclohexene
Draw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description.
a. a 1,1-disubstituted cyclohexane with an axial CH3CH2 group
b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group
c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group
d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 group
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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- CH3 2. Give the structure corresponding to each IUPAC name. a. 3-ethyl-3-methylhexane b. 2-ethyl-1-methyl-3-propylcyclopentane c. 3-methylbutane d. 1-ethyl-2,3-dimethylcyclopentane e. 1,5-dimethylcyclohexanearrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description. a.a 1,1-disubstituted cyclohexane with an axial CH3CH2 group b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 group.arrow_forward• Draw the chair conformations of the following compounds and determine which geometric isomer is more stable. Also show using Newman projection that one conformation is more stable than the other. a. cis-1-isopropyl-2-methylcyclohexane b. 1-methycyclohexanearrow_forward
- Choose the statement that is incorrect about rings. اختر احدى الاجابات А. Planar cyclobutane is its most stable conformation. В. Planar cyclopentane would have small angle strain but severe torsional strain. C. The chair conformation of cyclohexane has no angle or torsional strain. D. Cyclopropane has the greatest angle strain. Е. The chair conformation has less torsional strain and fewer nonbonded interactions than the twist boat conformation.arrow_forward4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3Carrow_forwardThe octane rating for gasoline is a measurement of how readily a fuelcombusts compared to 2,2,4-trimethylpentane, an isomer of octane.a. Draw 2,2,4-trimethylpentane and verify that it is an isomer ofoctane.b. Draw four other isomers of octane.c. Select one of the isomers and draw it such that it looksdifferent on the page but is still the exact same compound.d. Name this isomer.e. Define isomer using a complete sentence.arrow_forward
- Make a model of cyclohexane and draw its shape. Comment on its bond angles and how easily the model fitted together. Draw the boat and chair conformations of cyclohexane. Which arrangement do you think is the most stable?arrow_forwardLook at a cyclohexane model:a. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon 4. What is the resulting conformation? b. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon What is now the resulting conformation?arrow_forward4. 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_forward
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