Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3.14, Problem 3.25P
Draw the most stable conformation of
- a. ethylcydohexane.
- b. 3-isopropyl-1,1-dimethylcydohexane.
- c. cis-1-tert-butyl-4-isopropylcyclohexane.
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1. Identify the SYSTEMATIC name of the aliphatic hydrocarbon
a. 1-pentenyicyclopentane
b. 1-cyclopentylpent-2-yne
c. 1-pentenecyclopent-2-yne
d. 1-pentenyicyclopentane
2. Identify the SYSTEMATIC name of the aliphatic hydrocarbon
a. Trans-1,2-propylcyclopropane
b. Trans-1,2-diisopropylcyclopropane
c. Cis-1,2-propylcyclopropane
d. Cis-1,2-diisopropylcyclopropane
3. Identify the SYSTEMATIC name of the aliphatic hydrocarbon
3,10-dimethyl-2-decacen-6-yne
3,10-dimethyl-2-dodocen-6-yne
3,10-dimethyl-10-decacen-6-yne
d. 3,10-dimethyl-10-dodocen-6-yne
a.
b.
C.
4. Identify which type of isomer the following structures represent
HO
a. Skeletal Isomer
b. E/Z isomer
c. Cis/Trans isomer
OH
OH
d.
Positional isomer
5. Identify which type of isomer the following structures represent
a. Skeletal Isomer
Br
b. E/Z isomer
c Cis/Trans isomer
Br
d. Positional isomer
Draw a structure
a. 3,4-dimethylpent-1-yneb.3-methyl-3-ethyl-1-butenec. 3,3-dimethyl-4-decened.1,1-dimethyl-4-ethyl-2,5-cyclohexadienee. 4-ethyl-2,3-dimethyl-2-heptenef. 1-chlorocyclopropeneg. 2,6-dimethyl-2,5-octadieneh. 1-cyclobutyl-3-methyl-1-butynei. 5-bromo-2-chlorotoluene
1. a. Draw and name the five cycloalkane structures of formula C5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.
b. Draw and name the eight cycloalkane structures of formula C6H12 that do not show geometric isomerism.
c. Draw and name the four cycloalkanes of formula C6H12 that do have cis-trans isomers.
2. Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.
(a) an isopropylheptane (b) a diethyldecane (c) a cis-diethylcyclohexane
(d) a trans-dihalocyclopentane (e) a (2,3-dimethylpentyl)cycloalkane (f) a bicyclononane
3. 2. refer to the photo attached and answer the ff.3-33, 3-34
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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- 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_forward1. Draw the structure of each of the following cycloalkanes a. 1-Bromo-2-methylcyclobutaneb. 1,2-Dibromo-3-methylcyclohexanec. Iodocyclopropane2. How does the general formula of a cycloalkane compare to that of an alkane?arrow_forwardDetermine 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. methylcycloheptanearrow_forward
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