Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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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?
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ČH3
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(CH3)2CH
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H3C,
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H
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What is the preferred IUPAC name of the
alkene shown in Figure below?
CH3
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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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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
- 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 grouparrow_forwardCH3 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_forwardChoose 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_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_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. 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_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_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_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
- Analyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.arrow_forwardConsider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?arrow_forwardP. CH3-CH2-CH3 Q. CH3-CH2-CH=CH-CH3 R. CH3-CH2-CH2-CH2-CH3 S. CH3-CH=CH-CH2-CH3 Which compounds belong to the same homologous series? P and Q Q and R R and S P and R Which structures show unsaturated hydrocarbons? P and Q P and R Q and S R and Sarrow_forward
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