Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 4.12, Problem 39P
Which of the following compounds has a stereoisomer that is a meso compound?
- A 2,4-dibromohexane
- B 2,4-dibromopentane
- C 2,4-dimethylpentane
- D 1,3-dichlorocyclohexane
- E 1,4-dichlorocyclohexane
- F 1,2-dichlorocyclobutane
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Stereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of
trans-1,4-dibromocyclohexane
cis-1,2-dimethylcyclobutane
cis-1,3-dimethylcyclobutane
Name the following molecule.
CH₂CH3
H-CH3
H3C H
Br
(2R, 3R)-2-bromo-3-methylpentane
(2S,3S)-2-bromo-3-methylpentane
O (2R,3S)-2-bromo-3-methylpentane
(1R, 2S)-1-bromo-1,2-dimethylbutane
(1S,2R)-1-bromo-1,2-dimethylbutane
Which of the following has an achiral stereoisomer?
A 2,3-dichlorobutane B 2,3-dichloropentane C 2,3-dichloro-2,3-dimethylbutane D 1,3-dichlorocyclopentane E 1,3-dibromocyclobutane F 2,4-dibromopentane G 2,3-dibromopentane H 1,4-dimethylcyclohexane I 1,2-dimethylcyclopentane J 1,2-dimethylcyclobutane
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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- Which of the following is a position isomer of 3-methylhex-2-ene? 2,3-dimethylpent-2-ene, 1,3-dimethylcyclopentane, isobutylcyclopropane, 3-methylhex-1-enearrow_forwardName the compound shown below. Y 2,5,6-trimethylcyclohexene 1,4,5-trimethylcyclohexene 2,4,5-trimethylcyclohexene 2,4,6-trimethylcyclohexene 1,3,4-trimethylcyclohexene 1,3,5-trimethylcyclohexenearrow_forwardTell whether the following pairs of compounds are identical, constitutional isomers, stereoisomers, or unrelated. (a) cis-1, 3-Dibromocyclohexane and trans-1, 4-dibromocyclohexane (b) 2, 3-Dimethylhexane and 2, 3, 3-trimethy1pentanearrow_forward
- Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer: trans-1,4-difluorocyclohexane or cis-1-tert-butyl-3- fluorocyclohexane? O trans-1,4-difluorocyclohexane O cis-1-tert-butyl-3-fluorocyclohexanearrow_forwardWhich of the following is the correct name for the trisubstituted cycloheptane ring shown below? O 3-ethyl-1,4-dimethylcycloheptane O 1-ethyl-2,6-dimethylcycloheptane O 1-ethyl-3,7-dimethylcyloheptane O 2-ethyl-1,4-dimethylcycloheptanearrow_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
- 6) Draw the energetically favored (more stable) chair conformer of the following cyclohexane. H3C OH 110arrow_forwardWhat is the name of the following compound? H₂C 4,4-dibromo-6-chloro-1-ethyl-3-methylcyclohexane 2,2-dibromo-4-chloro-5-ethyl-1-methylcyclohexane 5,5-dibromo-1-chloro-2-ethyl-4-methylcyclohexane 1,1-dibromo-5-chloro-4-ethyl-2-methylcyclohexane What is the name of the following compound? H₂C H₂C- 4-cylcopropyl-3-ethyl-2,6-difluoro-5,5,6-trimethylhexane 4-cylcopropyl-3-ethyl-2,6-difluoro-5,5-dimethylheptane 4-cylcopropyl-5-ethyl-2,6-difluoro-3,3-dimethylheptane 3-cylcopropyl-4-ethyl-1,5-difluoro-1,2,2-trimethylhexane 0000 Ci H₂C. CH₂ Br CH₂ CH₂ Brarrow_forwardIndicate 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.arrow_forward
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