Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3.11, Problem 3.17P
Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers.
- a. 3-ethyl-1, 1-dimethylcyclohexane
- b. 1-ethyl-3-methy1cydoheptane
- c. 1-ethyl-3-methylcyclopentane
- d. 1-cydopropyl-2-methylcyclohexane
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Determine whether cis-trans isomerism is probable for the following cycloalkanes. If it is possible, draw structural formulas for the cis and trans isomers.
a. 1-ethyl-1-methylcyclopentane
b. ethylcyclohexane
c. 1,4-diethylcyclohexane
d. 1,1-dimethylcyclooctane
e. methylcycloheptane
Write skeletal formulas for the following alkanes and cycloalkanes. Use solid and broken lines to indicate stereochemistry.
a.3-ethyl-2,4,5-trimethyloctane
b.4-(1-methylethyl)octane
c.5-butyl-2,2-dimethylnonane
d.trans-1,3-dimethylcyclopentane
e.cis-1,2-diethylcyclobutane
1. Name and draw the isomers form from the given molecular formula.
a. C₂H16
b. C4H,Br₂
2. Draw the structure of each of the following cycloalkanes
a. 1-Bromo-2-methylcyclobutane
b.
1,2-Dibromo-3-methylcyclohexane
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
- How does the structure of a cycloalkane differ from that of a straight-chain or branched-chain alkane?arrow_forwardWhat is the difference in bonding and in general molecular formula between an alkene and a cycloalkane with the same number of carbon atoms?arrow_forwardSelect those compounds that can be correctly called unsaturated and classify each one as an alkene or an alkyne: a.CH3CH2CH3f. b.CH3CH=CHCH3g. c.h.CH2=CHCH2CH3 d.i. e.arrow_forward
- Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structurethat is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical? Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers. Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids? What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.arrow_forwardWhich of the following cycloalkanes could show geometric isomerism? For each that could, draw structural formulas, and name both the cis- and the trans- isomers. a. c. b. d.arrow_forwardWhat is the difference in bonding and in the general molecular formula between an alkene and an alkane with the same number of carbon atoms?arrow_forward
- What is the systematic name for this alkane? (a) nonane (b) 2-ethyl-5-methylhexane (c) 2,5-dimethyl heptane (d) dimethyloctanearrow_forwardIs the general formula of a cycloalkanes the same as the general formula of an alkane, CnH2n+2? Draw any structural diagram to illustrate your answer.arrow_forwardWhich of the following pairs of cycloalkanes represent structural isomers? a. b. c. d.arrow_forward
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