Organic Chemistry 8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
1 Covalent Bonding And Shapes Of Molecules 2 Alkanes And Cycloalkanes 3 Stereoisomerism And Chirality 4 Acids And Bases 5 Alkenes: Bonding, Nomenclature, And Properties 6 Reactions Of Alkenes 7 Alkynes 8 Haloalkanes, Halogenation, And Radical Reactions 9 Nucleophilic Substitution And Β-elimination 10 Alcohols 11 Ethers, Epoxides, And Sulfides 12 Infrared Spectroscopy 13 Nuclear Magnetic Resonance Spectroscopy 14 Mass Spectrometry 15 An Introduction To Organometallic Compounds 16 Aldehydes And Ketones 17 Carboxylic Acids 18 Functional Derivatives Of Carboxylic Acids 19 Enolate Anions And Enamines 20 Dienes, Conjugated Systems, And Pericyclic Reactions 21 Benzene And The Concept Of Aromaticity 22 Reactions Of Benzene And Its Derivatives 23 Amines 24 Catalytic Carbon-carbon Bond Formation 25 Carbohydrates 26 Lipids 27 Amino Acids And Proteins 28 Nucleic Acids 29 Organic Polymer Chemistry Chapter2: Alkanes And Cycloalkanes
2.1 The Structure Of Alkanes 2.2 Constitutional Isomerism In Alkanes 2.3 Nomenclature Of Alkanes And The Iupac System 2.4 Cycloalkanes 2.5 Conformations Of Alkanes And Cycloalkanes 2.6 Cis,trans Isomerism In Cycloalkanes And Bicycloalkanes 2.7 Physical Properties Of Alkanes And Cycloalkanes 2.8 Reactions Of Alkanes 2.9 Sources And Importance Of Alkanes Chapter Questions Section: Chapter Questions
Problem 2.16P: Write a line-angle formula for each condensed structural formula. (a) (b) (c) (CH3)2CHCH(CH3)2 (d)... Problem 2.17P: Write the molecular formula of each alkane. Problem 2.18P: Using parentheses and subscripts, provide an even more abbreviated formula for each structural... Problem 2.19P: Which statements are true about constitutional isomers? (a) They have the same molecular formula.... Problem 2.20P Problem 2.21P: Each member of the following set of compounds is an alcohol; that is, each contains an OH (hydroxyl... Problem 2.22P: Each of the following compounds is an amine (Section 1.3B). Which line-angle formulas represent the... Problem 2.23P: Each of the following compounds is either an aldehyde or a ketone (Section 1.3C). Which line-angle... Problem 2.24P: Draw structural formulas and write IUPAC names for the nine constitutional isomers with the... Problem 2.25P: Draw structural formulas for all of the following. (a) Alcohols with the molecular formula C4H10O... Problem 2.26P: Write IUPAC names for these alkanes and cycloalkanes. Problem 2.27P: Write structural formulas and line-angle formulas for the following alkanes and cycloalkanes. (a)... Problem 2.28P: Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended... Problem 2.29P: For each IUPAC name, draw the corresponding structural formula and line-angle formula. (a) Ethanol... Problem 2.30P: Write the IUPAC name for each compound. Problem 2.31P Problem 2.32P: Torsional strain resulting from eclipsed CH bonds is approximately 4.2 kJ (1.0 kcal)/mol, and that... Problem 2.33P: How many different staggered conformations are there for 2-methylpropane? How many different... Problem 2.34P: Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3... Problem 2.35P: Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest... Problem 2.36P: trans-1,4-Di-tert-butylcyclohexane exists in a normal chair conformation.... Problem 2.37P: From studies of the dipole moment of 1,2-dichloroethane in the gas phase at room temperature (25C),... Problem 2.38P Problem 2.39P: Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane. (a) Estimate... Problem 2.40P Problem 2.41P Problem 2.42P: Draw line-angle formulas for the cis and trans isomers of 1,2-dimethylcyclopropane. Problem 2.43P: Name and draw structural formulas for all cycloalkanes with molecular formula C5H10. Include cis and... Problem 2.44P: Using a planar pentagon representation for the cyclopentane ring, draw structural formulas for the... Problem 2.45P: Gibbs free energy differences between axial-substituted and equatorial-substituted chair... Problem 2.46P Problem 2.47P: Calculate the difference in Gibbs free energy in kilojoules per mole between the alternative chair... Problem 2.48P: Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane,... Problem 2.49P: Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and... Problem 2.50P: There are four cis,trans isomers of 2-isopropyl-5-methylcyclohexanol: (a) Using a planar hexagon... Problem 2.51P: Draw alternative chair conformations for each substituted cyclohexane and state which chair is more... Problem 2.52P: 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these... Problem 2.53P Problem 2.54P: What generalization can you make about the densities of alkanes relative to the density of water? Problem 2.55P: What unbranched alkane has about the same boiling point as water? (Refer to Table 2.5 on the... Problem 2.56P: Complete and balance the following combustion reactions. Assume that each hydrocarbon is converted... Problem 2.57P: Following are heats of combustion per mole for methane, propane, and 2,2,4-trimeth-ylpentane. Each... Problem 2.58P: Following are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which... Problem 2.59P: Without consulting tables, arrange these compounds in order of decreasing (less negative) heat of... Problem 2.60P: Which would you predict to have the larger (more negative) heat of combustion,... Problem 2.61P: Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used... Problem 2.62P: Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of... Problem 2.63P: On the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose... Problem 2.64P Problem 2.65P Problem 2.57P: Following are heats of combustion per mole for methane, propane, and 2,2,4-trimeth-ylpentane. Each...
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Concept explainers
Benzene has pi-bonds and should in theory undergo addition reactions like alkenes. However, we know that benzene only takes part in substitution reactions. Figure 16 compares the energy diagrams for the possible addition reactions and substitution reactions of benzene. Mark the correct statements. *
Addition and substitution reactions of benzene proceeds through the same reactive intermediate.
The substitution reaction is faster than the addition reaction.
Addition and substitution reactions of benzene are exothermic.
Both addition and substitution reactions of benzene proceeds through two transition states.
The substitution product is more stable than the addition product due to the stability of the aromatic ring.
Transcribed Image Text: addition product
benzene
substitution product
t (s)
E (kJ-mol")
Definition Definition Organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Aromatic organic compounds, also called arenes, are an important class of hydrocarbons under the branch of organic chemistry.
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