General, Organic, and Biological Chemistry
7th Edition
ISBN: 9781285853918
Author: H. Stephen Stoker
Publisher: Cengage Learning
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Textbook Question
Chapter 12, Problem 12.112EP
Determine the number of constitutional isomers that are possible for each of the following situations.
- a. Five-carbon cycloalkanes
- b. Six-carbon cycloalkanes where the ring has four carbon atoms
- c. Six-carbon cycloalkanes where the ring has three carbon atoms
- d. Seven-carbon cycloalkanes where the ring has four carbon atoms
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1. Which of the following families of organic compounds share the same general molecular formula with normal chain alkynes?
a. Alkanes and alkenes
b. Alkanes and bicycloalkanes
c. Cycloalkenes and bicycloalkanes
d. Cycloalkenes and alkenes
e. Cycloalkanes and cycloalkenes
1. 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?
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
Chapter 12 Solutions
General, Organic, and Biological Chemistry
Ch. 12.1 - Prob. 1QQCh. 12.1 - Prob. 2QQCh. 12.2 - Prob. 1QQCh. 12.2 - Prob. 2QQCh. 12.3 - Prob. 1QQCh. 12.3 - Prob. 2QQCh. 12.4 - Prob. 1QQCh. 12.4 - Prob. 2QQCh. 12.4 - Prob. 3QQCh. 12.5 - Prob. 1QQ
Ch. 12.5 - Prob. 2QQCh. 12.5 - Prob. 3QQCh. 12.6 - Prob. 1QQCh. 12.6 - Prob. 2QQCh. 12.6 - Prob. 3QQCh. 12.6 - Prob. 4QQCh. 12.7 - Prob. 1QQCh. 12.7 - Prob. 2QQCh. 12.8 - Prob. 1QQCh. 12.8 - Prob. 2QQCh. 12.8 - Prob. 3QQCh. 12.8 - Prob. 4QQCh. 12.8 - Prob. 5QQCh. 12.8 - Prob. 6QQCh. 12.8 - Prob. 7QQCh. 12.9 - Prob. 1QQCh. 12.9 - Prob. 2QQCh. 12.10 - Prob. 1QQCh. 12.10 - Prob. 2QQCh. 12.11 - Prob. 1QQCh. 12.11 - Prob. 2QQCh. 12.11 - Prob. 3QQCh. 12.12 - Prob. 1QQCh. 12.12 - Prob. 2QQCh. 12.12 - Prob. 3QQCh. 12.13 - Prob. 1QQCh. 12.13 - Prob. 2QQCh. 12.13 - Prob. 3QQCh. 12.14 - Prob. 1QQCh. 12.14 - Prob. 2QQCh. 12.14 - Prob. 3QQCh. 12.15 - Prob. 1QQCh. 12.15 - Prob. 2QQCh. 12.16 - Prob. 1QQCh. 12.16 - Prob. 2QQCh. 12.16 - Prob. 3QQCh. 12.17 - Prob. 1QQCh. 12.17 - Prob. 2QQCh. 12.17 - Prob. 3QQCh. 12.17 - Prob. 4QQCh. 12.18 - Prob. 1QQCh. 12.18 - Prob. 2QQCh. 12.18 - Prob. 3QQCh. 12.18 - Prob. 4QQCh. 12 - Prob. 12.1EPCh. 12 - Prob. 12.2EPCh. 12 - Prob. 12.3EPCh. 12 - Prob. 12.4EPCh. 12 - Indicate whether each of the following situations...Ch. 12 - Indicate whether each of the following situations...Ch. 12 - Prob. 12.7EPCh. 12 - Prob. 12.8EPCh. 12 - What is the difference between a saturated...Ch. 12 - Prob. 12.10EPCh. 12 - Prob. 12.11EPCh. 12 - Prob. 12.12EPCh. 12 - Prob. 12.13EPCh. 12 - Prob. 12.14EPCh. 12 - Prob. 12.15EPCh. 12 - Prob. 12.16EPCh. 12 - Prob. 12.17EPCh. 12 - Prob. 12.18EPCh. 12 - Convert the expanded structural formulas in...Ch. 12 - Prob. 12.20EPCh. 12 - Prob. 12.21EPCh. 12 - Prob. 12.22EPCh. 12 - Prob. 12.23EPCh. 12 - Prob. 12.24EPCh. 12 - Prob. 12.25EPCh. 12 - Prob. 12.26EPCh. 12 - Indicate whether each of the following would be...Ch. 12 - Indicate whether each of the following would be...Ch. 12 - Prob. 12.29EPCh. 12 - Prob. 12.30EPCh. 12 - Prob. 12.31EPCh. 12 - Prob. 12.32EPCh. 12 - Prob. 12.33EPCh. 12 - How many of the numerous seven-carbon alkane...Ch. 12 - Prob. 12.35EPCh. 12 - For each of the following pairs of structures,...Ch. 12 - Prob. 12.37EPCh. 12 - Prob. 12.38EPCh. 12 - Prob. 12.39EPCh. 12 - Prob. 12.40EPCh. 12 - Prob. 12.41EPCh. 12 - What is the name of the IUPAC prefix associated...Ch. 12 - What is the IUPAC name for each of the following...Ch. 12 - What is the IUPAC name for each of the following...Ch. 12 - Prob. 12.45EPCh. 12 - What is the chemical formula for each of the...Ch. 12 - Prob. 12.47EPCh. 12 - Prob. 12.48EPCh. 12 - Prob. 12.49EPCh. 12 - Prob. 12.50EPCh. 12 - Prob. 12.51EPCh. 12 - Prob. 12.52EPCh. 12 - Draw a condensed structural formula for each of...Ch. 12 - Draw a condensed structural formula for each of...Ch. 12 - Prob. 12.55EPCh. 12 - Prob. 12.56EPCh. 12 - Explain why the name given for each of the...Ch. 12 - Prob. 12.58EPCh. 12 - Indicate whether or not the two alkanes in each of...Ch. 12 - Prob. 12.60EPCh. 12 - How many of the 18 C8 alkane constitutional...Ch. 12 - Prob. 12.62EPCh. 12 - Prob. 12.63EPCh. 12 - Prob. 12.64EPCh. 12 - Prob. 12.65EPCh. 12 - Prob. 12.66EPCh. 12 - Do the line-angle structural formulas in each of...Ch. 12 - Do the line-angle structural formulas in each of...Ch. 12 - Convert each of the condensed structural formulas...Ch. 12 - Convert each of the condensed structural formulas...Ch. 12 - Assign an IUPAC name to each of the compounds in...Ch. 12 - Prob. 12.72EPCh. 12 - Prob. 12.73EPCh. 12 - Prob. 12.74EPCh. 12 - For each of the alkane structures in Problem...Ch. 12 - Prob. 12.76EPCh. 12 - Prob. 12.77EPCh. 12 - Prob. 12.78EPCh. 12 - Prob. 12.79EPCh. 12 - Prob. 12.80EPCh. 12 - Prob. 12.81EPCh. 12 - Prob. 12.82EPCh. 12 - Draw condensed structural formulas for the...Ch. 12 - Draw condensed structural formulas for the...Ch. 12 - To which carbon atoms in a hexane molecule can...Ch. 12 - Prob. 12.86EPCh. 12 - Prob. 12.87EPCh. 12 - Prob. 12.88EPCh. 12 - Prob. 12.89EPCh. 12 - Prob. 12.90EPCh. 12 - Prob. 12.91EPCh. 12 - Prob. 12.92EPCh. 12 - Prob. 12.93EPCh. 12 - Using the general formula for a cycloalkane,...Ch. 12 - Prob. 12.95EPCh. 12 - Prob. 12.96EPCh. 12 - Prob. 12.97EPCh. 12 - Prob. 12.98EPCh. 12 - How many secondary carbon atoms are present in...Ch. 12 - Prob. 12.100EPCh. 12 - Prob. 12.101EPCh. 12 - Assign an IUPAC name to each of the following...Ch. 12 - Prob. 12.103EPCh. 12 - What is wrong with each of the following attempts...Ch. 12 - Draw line-angle structural formulas for the...Ch. 12 - Draw line-angle structural formulas for the...Ch. 12 - Prob. 12.107EPCh. 12 - Prob. 12.108EPCh. 12 - Prob. 12.109EPCh. 12 - Prob. 12.110EPCh. 12 - Determine the number of constitutional isomers...Ch. 12 - Determine the number of constitutional isomers...Ch. 12 - Prob. 12.113EPCh. 12 - Determine whether cistrans isomerism is possible...Ch. 12 - Prob. 12.115EPCh. 12 - Prob. 12.116EPCh. 12 - Prob. 12.117EPCh. 12 - Indicate whether the members of each of the...Ch. 12 - Prob. 12.119EPCh. 12 - Prob. 12.120EPCh. 12 - Prob. 12.121EPCh. 12 - Prob. 12.122EPCh. 12 - Which member in each of the following pairs of...Ch. 12 - Prob. 12.124EPCh. 12 - Prob. 12.125EPCh. 12 - Prob. 12.126EPCh. 12 - Answer the following questions about the...Ch. 12 - Prob. 12.128EPCh. 12 - Prob. 12.129EPCh. 12 - Prob. 12.130EPCh. 12 - Prob. 12.131EPCh. 12 - Prob. 12.132EPCh. 12 - Prob. 12.133EPCh. 12 - Write structural formulas for all the possible...Ch. 12 - Assign an IUPAC name to each of the following...Ch. 12 - Assign an IUPAC name to each of the following...Ch. 12 - Prob. 12.137EPCh. 12 - Prob. 12.138EPCh. 12 - Prob. 12.139EPCh. 12 - Draw structural formulas for the following...Ch. 12 - Prob. 12.141EPCh. 12 - Prob. 12.142EPCh. 12 - Prob. 12.143EPCh. 12 - Prob. 12.144EPCh. 12 - Prob. 12.145EPCh. 12 - Prob. 12.146EPCh. 12 - Prob. 12.147EPCh. 12 - Prob. 12.148EP
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- What is the difference in bonding and in general molecular formula between an alkene and a cycloalkane with the same number of carbon atoms?arrow_forwardHow does the structure of a cycloalkane differ from that of a straight-chain or branched-chain alkane?arrow_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_forward
- What 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_forwardDistinguish 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_forwardWrite 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-diethylcyclobutanearrow_forward
- 2. Determine whether cis-trans isomerism is possible for each of the following cycloalkanes. If so, then draw structural formulas for the cis and trans isomers.. a. Methylcyclohexane b. 1,1-Dimethylcyclohexane c. 1,3-Dimethylcyclobutane d. 1-Ethyl-2-methylcyclobutanearrow_forwardWrite the general formula for an alkane, a cycloalkane, and a bicycloalkane. How do these general formulas differ?arrow_forwardExplain the process of Naming Cycloalkanes ?arrow_forward
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