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All Textbook Solutions for Organic And Biological Chemistry

1QQ 2QQ Which of the following statements about the covalent bonding capabilities of carbon atoms is incorrect? a. Single bond formation to another atom is possible. b. Double bond formation to another atom is possible. c. Triple bond formation to another atom is possible. d. no correct response 2QQ 1QQ 2QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ 1QQ 2QQ 3QQ 4QQ 5QQ 6QQ 7QQ 1QQ 2QQ 1QQ 2QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ 3QQ 4QQ 1.1EP 1.2EP 1.3EP 1.4EP Indicate whether each of the following situations meets or does not meet the bonding requirement for carbon atoms. a. Two single bonds and a double bond b. A single bond and two double bonds c. Three single bonds and a triple bond d. A double bond and a triple bond Indicate whether each of the following situations meets or does not meet the bonding requirement for carbon atoms. a. Four single bonds b. Three single bonds and a double bond c. Two double bonds and two single bonds d. Two double bonds 1.7EP 1.8EP What is the difference between a saturated hydrocarbon and an unsaturated hydrocarbon?What structural feature is present in an unsaturated hydrocarbon that is not present in a saturated hydrocarbon?1.11EP 1.12EP 1.13EP 1.14EP 1.15EP 1.16EP Convert the expanded structural formulas in Problem 12-15 into condensed structural formulas where parentheses and a subscript are used to denote the number of CH2 groups present.1.18EP 1.19EP 1.20EP 1.21EP 1.22EP 1.23EP 1.24EP 1.25EP 1.26EP Indicate whether each of the following would be expected to be the same or different for two alkane constitutional isomers. a. Number of hydrogen atoms present in a molecule b. Condensed structural formula c. Boiling point d. Melting point Indicate whether each of the following would be expected to be the same or different for two alkane constitutional isomers. a. Number of carbon atoms present in a molecule b. Shape of molecule c. Density d. Molecular formula 1.29EP Explain why two different straight-chain alkanes could not be constitutional isomers.With the help of Table 12-1, indicate how many constitutional isomers exist for each of the following. a. Four-carbon alkanes b. Six-carbon alkanes c. Eight-carbon alkanes d. Ten-carbon alkanes 1.32EP How many of the numerous eight-carbon alkane constitutional isomers are continuous-chain alkanes?How many of the numerous seven-carbon alkane constitutional isomers are continuous-chain alkanes?For each of the following pairs of structures, determine whether they are 1. Different conformations of the same molecule 2. Different compounds that are constitutional isomers 3. Different compounds that are not constitutional isomers a. b. c. d.For each of the following pairs of structures, determine whether they are 1. Different conformations of the same molecule 2. Different compounds that are constitutional isomers 3. Different compounds that are not constitutional isomers a. b. c. d.Convert each of the following linear condensed structural formulas into regular condensed structural formulas. a. CH3CH2CH(CH3)CH2CH3 b. (CH3)2CHCH2CH(CH3)2 c. CH3CH(CH3)CH3 d. CH3CH2CH(CH2CH3)CH2CH3 1.38EP 1.39EP 1.40EP 1.41EP 1.42EP 1.43EP 1.44EP 1.45EP 1.46EP 1.47EP 1.48EP 1.49EP 1.50EP 1.51EP 1.52EP Draw a condensed structural formula for each of the following alkanes. a. 3,4-Dimethylhexane b. 3-Ethyl-3-methylpentane c. 3,5-Diethyloctane d. 4-Propylnonane Draw a condensed structural formula for each of the following alkanes. a. 2,4-Dimethylhexane b. 5-Propyldecane c. 2,3,4-Trimethyloctane d. 3-Ethyl-3-methylheptane 1.55EP For each of the alkanes in Problem 12-54, determine (a) the number of alkyl groups present and (b) the number of substituents present. Draw a condensed structural formula for each of the following alkanes. a. 2,4-Dimethylhexane b. 5-Propyldecane c. 2,3,4-Trimethyloctane d. 3-Ethyl-3-methylheptane Explain why the name given for each of the following alkanes is not the correct IUPAC name. Then give the correct IUPAC name for the compound. a. 2-Ethyl-2-methylpropane b. 2,3,3-Trimethylbutane c. 3-Methyl-4-ethylhexane d. 2-Methyl-4-methylhexane 1.58EP Indicate whether or not the two alkanes in each of the following pairs of alkanes are constitutional isomers. a. Butane and pentane b. 2-Methylhexane and 3-methylhexane c. Butane and 2-methylpropane d. 2-Methylhexane and 3,3-dimethylpentane 1.60EP How many of the 18 C8 alkane constitutional isomers are named using the following base-chain names? a. Octane b. Heptane c. Hexane d. Pentane How many of the nine C7 alkane constitutional isomers are named using the following base-chain names? a. Heptane b. Hexane c. Pentane d. Butane 1.63EP 1.64EP 1.65EP 1.66EP Do the line-angle structural formulas in each of the following sets represent (1) the same compound, (2) constitutional isomers, or (3) different compounds that are not constitutional isomers? a. b.Do the line-angle structural formulas in each of the following sets represent (1) the same compound, (2) constitutional isomers, or (3) different compounds that are not constitutional isomers? a. b.Convert each of the condensed structural formulas in Problem 12-51 to a line-angle structural formula. a. b. c. d.Convert each of the condensed structural formulas in Problem 12-52 to a line-angle structural formula. a. b. c. d.Assign an IUPAC name to each of the compounds in Problem 12-63. a. b. c. d.1.72EP 1.73EP 1.74EP For each of the alkane structures in Problem 12-51, give the number of (a) primary, (b) secondary, (c) tertiary, and (d) quaternary carbon atoms present. a. b. c. d.For each of the alkane structures in Problem 12-52, give the number of (a) primary, (b) secondary, (c) tertiary, and (d) quaternary carbon atoms present. a. b. c. d.1.77EP 1.78EP 1.79EP 1.80EP 1.81EP 1.82EP Draw condensed structural formulas for the following branched alkanes. a. 5-(sec-Butyl)decane b. 4,4-Diisopropyloctane c. 5-Isobutyl-2,3-dimethylnonane d. 4-(1,1-Dimethylethyl)octane Draw condensed structural formulas for the following branched alkanes. a. 5-Isobutylnonane b. 4,4-Di(sec-butyl)decane c. 4-(tert-Butyl)-3,3-diethylheptane d. 5-(2-Methylpropyl)nonane To which carbon atoms in a hexane molecule can each of the following alkyl groups be attached without extending the longest carbon chain beyond six carbons? a. Ethyl b. Isopropyl c. Isobutyl d. tert-Butyl 1.86EP 1.87EP 1.88EP Give an acceptable alternate name for each of the following branched-chain alkyl groups. a. Isopropyl group b. tert-Butyl group c. (1-Methylpropyl) group d. (2-Methylpropyl) group 1.90EP 1.91EP 1.92EP 1.93EP 1.94EP What is the molecular formula for each of the following cycloalkane molecules? a. b. c. d.1.96EP 1.97EP 1.98EP 1.99EP How many secondary carbon atoms are present in each of the structures in Problem 12-96? a. b. c. d.Assign an IUPAC name to each of the following cycloalkanes. a. b. c. d.Assign an IUPAC name to each of the following cycloalkanes. a. b. c. d.1.103EP 1.104EP 1.105EP 1.106EP What is the molecular formula for each of the following hydrocarbons? a. 1,2-Dimethylcyclohexane b. 1,3-Dimethylcyclohexane c. 2,2-Dimethylhexane d. 2,3-Dimethylhexane 1.108EP 1.109EP 1.110EP 1.111EP 1.112EP Determine whether cistrans isomerism is possible for each of the following cycloalkanes. If it is, then draw structural formulas for the cis and irons isomers. a. Isopropylcyclobutane b. 1,2-Diethylcyclopropane c. 1-Ethyl-1-propylcyclopentane d. 1,3-Dimethylcyclohexane 1.114EP 1.115EP 1.116EP 1.117EP Indicate whether the members of each of the following pairs of hydrocarbons are (1) constitutional isomers, (2) stereoisomers, or (3) not isomers. a. 2-Methylpentane and cyclopentane b. 2-Methylpentane and 2-ethylpentane c. Ethylcyclohexane and 1,2-dimethylcyclohexane d. cis-l,3-Diethylcyclobutane and trans-1,3-diethylcyclobutane 1.119EP 1.120EP 1.121EP 1.122EP 1.123EP Which member in each of the following pairs of compounds has the higher boiling point? a. Methane and ethane b. Cyclohexane and hexane c. Butane and methylpropane d. Pentane and 2,2-dimethylpropane 1.125EP 1.126EP Answer the following questions about the unbranched alkane that contains six carbon atoms. a. Is it a solid, liquid, or gas at room temperature? b. Is it less dense or more dense than water? c. Is it soluble or insoluble in water? d. Is it flammable or nonflammable in air?1.128EP 1.129EP 1.130EP Write molecular formulas for all the possible halogenated hydrocarbon products from the bromination of methane.Write molecular formulas for all the possible halogenated hydrocarbon products from the fluorination of methane.1.133EP 1.134EP 1.135EP Assign an IUPAC name to each of the following halogenated hydrocarbons. a. CH3CH2CH2CH2Br b. c. d.1.137EP 1.138EP 1.139EP 1.140EP 1.141EP 1.142EP 1.143EP 1.144EP 1.145EP 1.146EP Give the IUPAC names for the eight isomeric halogenated hydrocarbons that have the molecular formula C5H11Cl.1.148EP 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 1QQ 2QQ 1QQ 2QQ 1QQ 2QQ 3QQ 4QQ 5QQ 1QQ 2QQ 3QQ 4QQ 5QQ 1QQ 2QQ 3QQ 4QQ 5QQ 1QQ 2QQ 3QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ 3QQ 4QQ 1QQ 2QQ Classify each of the following hydrocarbons as saturated or unsaturated. a. CH3CH2CH3 b. CH3CH=CH2 c. CH3CCH d. CH3CH=CHCH3 2.2EP 2.3EP 2.4EP 2.5EP 2.6EP 2.7EP Characterize the physical properties of saturated and unsaturated hydrocarbons as being similar or dissimilar.2.9EP 2.10EP 2.11EP 2.12EP 2.13EP 2.14EP What is the name of the spatial arrangement for bonds about a carbon atom that participates in one carboncarbon double bond?2.16EP 2.17EP 2.18EP Draw a condensed structural formula for each of the following unsaturated hydrocarbons. a. 3-Methyl-1-pentene b. 3-Methylcyclopentene c. 1,3-Butadiene d. 3-Ethyl-1,4-pentadiene 2.20EP The following names are incorrect by IUPAC rules. Determine the correct IUPAC name for each compound. a. 2-Ethyl-2-pentene b. 4,5-Dimethyl-4-hexene c. 3,5-Cyclopentadiene d. l,2-Dimethyl-4-cyclohexene The following names are incorrect by IUPAC rules. Determine the correct IUPAC name for each compound. a. 2-Methyl-4-pentene b. 3-Methyl-2,4-pentadiene c. 3-Methyl-3-cyclopentene d. 1,2-Dimethyl-3-cyclohexene 2.23EP Draw a condensed structural formula for each of the following unsaturated hydrocarbons. a. Propylene b. Methylenecyclopentane c. Vinyl iodide d. Allyl chloride 2.25EP Classify each of the following compounds as saturated or unsaturated. a. 2-methylcyclopentene b. 1,3-cyclopentadiene c. 2,3-dimethylpentane d. 1-ethyl-2-methylcyclohexene 2.27EP How many hydrogen atoms are present in a molecule of each of the compounds in Problem 13-26? a. 2-methylcyclopentene b. 1,3-cyclopentadiene c. 2,3-dimethylpentane d. 1-ethyl-2-methylcyclohexene Draw a line-angle structural formula for each of the following unsaturated hydrocarbons. a. 1-Butene b. 2-Butene c. 1,3-Butadiene d. 3-Methyl-l-butene Draw a line-angle structural formula for each of the following unsaturated hydrocarbons. a. 1-Pentene b. 2-Pentene c. 1,4-Pentadiene d. 4-Methyl-2-pentene 2.31EP 2.32EP 2.33EP 2.34EP 2.35EP 2.36EP 2.37EP 2.38EP For each of the following pairs of alkenes, indicate whether the members of each pair are positional constitutional isomers or skeletal constitutional isomers. a. 1-Hexene and 2-hexene b. 2-Methyl-1-pentene and 3-methyl-1-pentene c. 3-Hexene and 2-ethyl-1-butene d. 3-Methyl-2-pentene and 3-methyl-1-pentene For each of the following pairs of alkenes, indicate whether the members of each pair are positional constitutional isomers or skeletal constitutional isomers. a. 2-Hexene and 3-hexene b. 4-Methyl-1-pentene and 4-methyl-2-pentene c. 2,3-Dimethyl-2-butene and 3,3-dimethyl-1-butene d. 2-Methyl-2-pentene and 2-methyl-1-pentene 2.41EP 2.42EP 2.43EP 2.44EP

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