Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 2, Problem 2.40P
Interpretation Introduction
Interpretation:
The structural feature of cyclohexane that makes cis, trans isomerism possible in them has to be given.
Concept Introduction:
Cis, trans isomers:
Stereoisomers that have the same connectivity but a different arrangement of their atoms in space as a result of the presence of either a ring or a carbon-carbon double bond.
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Draw three cycloalkanes which are structural (constitutional) isomers of C6H12. At
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Chapter 2 Solutions
Organic Chemistry
Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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- 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_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_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_forwardSummarize the nomenclature rules for alkanes, alkenes, alkynes, and aromatic compounds. Correct the following false statements regarding nomenclature of hydrocarbons. a. The root name for a hydrocarbon is based on the shortest continuous chain of carbon atoms. b. The suffix used to name all hydrocarbons is -ane. c. Substituent groups are numbered so as to give the largest numbers possible. d. No number is required to indicate the positions of double or triple bonds in alkenes and alkynes. e. Substituent groups get the lowest number possible in alkenes and alkynes. f. The ortho- term in aromatic hydrocarbons indicates the presence of two substituent groups bonded to carbon- 1 and carbon-3 in benzene.arrow_forwardWhat is meant by the term “unsaturated hydrocarbon”? What structural feature characterizes unsaturated hydrocarbons?arrow_forward
- What is the difference between the hybridization of carbon atoms' valence orbitals in saturated and unsaturated hydrocarbons?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_forward1. 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, 3-34arrow_forward
- 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 stereoisomersarrow_forwardYou are teaching a class in organic chemistry to grade 12 students. Outline the differences in 3 physical properties between alkanes, alcohols, and carboxylic acids. Note: they all have the same hydrocarbon length.arrow_forwardDraw and name the eight cycloalkane structures of formula C6H12 that do not show geometric isomerism.arrow_forward
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