Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 4, Problem 47P
Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?
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Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?
Indicate the relationship between the two structures in the pair. Are they chair conformations of the same molecule? If so,
are they conformational diastereomers, conformational enantiomers, or identical? If they are not conformations of the
same molecule, what is their stereochemical relationship?
CH₂
CH₂
H₂C
H₂C
CH₂
Which statement is true?
Ho
CH₂
They are chair conformations of the same molecule, and they are conformational enantiomers.
They are different molecules, and they are enantiomers.
They are different molecules, and they are diastereomers.
They are identical conformations of the same molecule.
They are chair conformations of the same molecule, and they are conformational diastereomers.
Is there a difference in the stability of the two cyclohexane conformations?
Chapter 4 Solutions
Essential Organic Chemistry, Global Edition
Ch. 4.1 - Draw the cis and trans isomers for the following:...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Prob. 6PCh. 4.2 - Prob. 7PCh. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:Ch. 4.2 - Draw the structure of (Z)-2,3-dimethyl-3-heptene.
Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Assign relative priorities to the groups or atoms...Ch. 4.7 - Name the following:Ch. 4.7 - Prob. 22PCh. 4.7 - Draw a perspective formula for each of the...Ch. 4.8 - Prob. 24PCh. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - Prob. 29PCh. 4.9 - Prob. 30PCh. 4.10 - Prob. 31PCh. 4.10 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.11 - Prob. 34PCh. 4.11 - a. Draw the stereoisomers of...Ch. 4.11 - Prob. 37PCh. 4.11 - Prob. 38PCh. 4.12 - Which of the following compounds has a...Ch. 4.12 - Draw all the stereoisomers for each of the...Ch. 4.12 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Which of the following have an asymmetric center?...Ch. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Of all the possible cyclooctanes that have one...Ch. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Draw the stereoisomers of 2,4-dichlorohexane....Ch. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Prob. 62PCh. 4 - Draw structures for each of the following: a....Ch. 4 - Prob. 64PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Chloramphenicol is a broad-spectrum antibiotic...
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- Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardFill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.arrow_forwardFollowing is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forward
- How many unique stereoisomers exist for 1,2,3,4,5-pentachlorocyclohexane?arrow_forwardThe following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?arrow_forwardIt is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D configuration and what conformation (axial,equatorial) would each of the three ethyl groups be in for the most stable configuration.arrow_forward
- Write two chair conformations of the cis-1-ethyl-2-methylcyclohexane. Decide which one is stable and explain your answer.arrow_forwardDraw a structural formula of the S configuration of the compound shown below. • Use the wedge /hash bond tools to indicate stereochemistry where it exists. Include H atoms at chiral centers only. • Ifa group is achiral, do not use wedged or hashed bonds on it. CH3 CH3 CH;CHCHCN CH,CH,CH,CHCH,CH, CH2NH2 Draw a structural formula of the RS configuration of the compound shown below. Use the wedge /hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. If a group is achiral, do not use wedged or hashed bonds on it. ÇIarrow_forwardwhat is the most stable conformation of (1R, 2S, 5R)-1,2,5-trimethylcyclohexanearrow_forward
- trans-1,4-Di-tert-butylcyclohexane exists in a normal chair conformation. cis-1,4-Di-tertbutylcyclohexane, however, adopts a twist-boat conformation. Draw both isomers and explain why the cis isomer is more stable in a twist-boat conformation.arrow_forwardWhich of the following two conformations of trans-3-methylcyclohexanol is more stable? Use the strain energy increments in the table below estimate the energy difference (a positive number) between them.arrow_forwardFor the following chair conformations of 1,2-dibromocyclohexane, determine the orientations of the two substituents, and determine if the conformation is cis or trans. Br Br Br Br Br Br Br Br Structure A Orientation: Conformation: Structure D Orientation: Conformation:arrow_forward
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