Test Bank for Organic Chemistry, 8th Edition

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1Chapter 1—Structure and BondingSHORT ANSWER1.Give the ground-state electron configuration for carbon (atomic number 6).ANS:1s22s22px12py1or 1s22s22p22.Give the ground-state electron configuration for fluorine (atomic number 9).ANS:1s22s22px22py22pz1or 1s22s22p53.Give the ground-state electron configuration for magnesium (atomic number 12).ANS:1s22s22p63s24.How many electrons does silicon have in its valence shell?ANS:fourExhibit 1-1Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots andshow all non-bonding electrons.5.C2Cl4tetrachloroethyleneANS:6.CO2carbon dioxideANS:7.CH4Omethanol

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Structure and Bonding2ANS:Exhibit 1-2Consider the structure of urea, shown below, to answer the following question(s).8.Refer to Exhibit 1-2. Fill in any non-bonding valence electrons that are missing from theline-bond structure.ANS:9.Refer to Exhibit 1-2. The carbon atom in urea is:a.sp3hybridizedb.sp2hybridizedc.sphybridizedd.not hybridizedANS:b10.Refer to Exhibit 1-2. The predicted NH2−C=O bond angle in urea is:a.109.5°b.120°c.180°d.not predictableANS:b

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Chapter 13Exhibit 1-3Determine the hybridization for the indicated atoms in each structure below.11.Refer to Exhibit 1-3. The hybridization of this oxygen atom (A) is ______.ANS:sp212.Refer to Exhibit 1-3. The hybridization of this oxygen atom (B) is ______.ANS:sp313.Refer to Exhibit 1-3. The hybridization of this carbon atom (C) is ______.ANS:sp314.Refer to Exhibit 1-3. The hybridization of this carbon atom (D) is ______.ANS:sp15.The molecular formula C2H4O can be converted into three-line bond (Kekulé) structures thatare consistent with valence rules.a.b.c.d.a.Which one of the Kekulé structures isnotconsistent with valence rules?b.Explain why the structure you chose in partais not consistent with valence rules.ANS:a.db.The carbon bonded to the oxygen atom in structure d is pentavalent; it has 10 valenceelectrons. Carbon can only have eight valence electrons. In addition, the other carbonhas only six valence electrons when it would prefer to have eight.

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Structure and Bonding416.The original question was combined with #15. This placeholder question is here to maintainthe integrity of the numbering system between the printed copy and ExamView. Therefore,it has been marked "do not use on test" in ExamView's question information dialog. As aresult, this placeholder question is automatically prevented from being chosen as a testquestion.ANS:Answer not provided.17.Convert the following structure to a skeletal drawing and give its molecular formula.ANS:Molecular formula: C5H7Br18.Draw an orbital picture for acetylene, C2H2. Clearly label each bond type and indicate thetype of orbitals involved in each bond.ANS:

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Chapter 15Exhibit 1-4Propose possible structures for a molecule that meets each of the following descriptions.19.Refer to Exhibit 1-4. Contains twosp3hybridized carbons and twosphybridized carbons.ANS:20.Refer to Exhibit 1-4. Contains onesp3hybridized carbon and twosp2hybridized carbons.ANS:21.Convert the following molecular model into a condensed structure and a skeletal structure.ANS:22.Convert the following molecular model into a condensed structure and a skeletal structure.

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Structure and Bonding6ANS:23.Convert the following molecular model into a condensed structure and a skeletal structure.ANS:or more specifically;24.Indicate the hybridization on each of the carbon atoms indicated with a number in themolecular model shown.ANS:Carbon 1:sp3Carbon 2:sp2

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Chapter 1725.Draw the orbital diagram showing the ground-state electron configuration of sulfur.ANS:26.Fill in any nonbonding valence electrons that are missing from the following structuralrepresentation of the amino acid cysteine.ANS:27.There are two substances with the molecular formula C2H7N. Draw them and describe howthey differ.ANS:The two structures differ in the number of hydrogen atoms and carbon atoms bonded to thenitrogen atom.The first structure contains the carbon atoms bonded in a two carbon chain whilein the second structure the two carbons atoms are isolated from each other by the nitrogen atom.

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Structure and Bonding8MULTIPLE CHOICE1.Overlap of the two atomic orbitals shown could result in a:a.σbondb.πbondc.σorπdepending on the direction of the overlap.ANS: C2.Hybridization of the atomic orbitals shown would result in:a.sp3hybridizationb.sp2hybridizationc.sphybridizationANS: B3.Which of the following represents a hybrid orbital?a.c.b.d.

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Chapter 19ANS: D4.What type of hybridization is exhibited by carbon in the following substance?:a.sp3hybridizationb.sp2hybridizationc.sphybridizationANS: B5.What type of hybridization is exhibited by carbon in the following substance?:a.sp3hybridizationb.sp2hybridizationc.sphybridizationANS: C6.What type of hybridization is exhibited by the nitrogen atom in the following substance andhow many lone pairs are present on the nitrogen?:a.sp3hybridization and 1 lone pairb.sp2hybridization and l lone pairc.sphybridization and 1 lone paird.sp3hybridization and 2 lone pairs

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Structure and Bonding10e.sp2hybridization and 2 lone pairsf.sphybridization and 2 lone pairsANS: A7.If all the missing bonds in the following structure are sigma bonds to hydrogen atoms, howmany hydrogen atoms are missing from this structure? Atoms other than carbon are labeled.a.7b.10c.12d.14e.None of these is the correct number.ANS: E

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1Chapter 2—Polar Covalent Bonds; Acids and BasesSHORT ANSWERExhibit 2-1Give the letter of the term that best matches the given definition.a.Brønsted-Lowry Acidf.Ionic Bondb.Brønsted-Lowry Baseg.Covalent Bondc.Lewis Acidh.Polar-Covalent Bondd.Lewis Basei.Hydrophobice.Electronegativityj.Hydrophilic1._____ Any species that can accept electrons.ANS:c2._____ A bond between two atoms differing in electronegativity by 0.5−2.ANS:h3._____ A term used to describe a "water loving" species.ANS:j4._____ A compound that can donate a proton.ANS:aPTS: 15._____ The ability of an atom to attract the shared electrons in a covalent bond.ANS:e6._____ A term used to describe a "water fearing" species.ANS:i

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Polar Covalent Bonds: Acids and Bases27._____ Any species that can donate electrons.ANS:d8._____ A bond between two atoms differing in electronegativity by < 0.5.ANS:g9._____ A compound that can accept a proton.ANS:b10._____ A bond between two atoms differing in electronegativity by > 2.ANS:fExhibit 2-2Calculate the formal charges on the indicated atoms in each compound below.11.Refer to Exhibit 2-2. The formal charge on phosphorous (A) is ______.ANS:+112.Refer to Exhibit 2-2. The formal charge on oxygen (B) is ______.ANS:−113.Refer to Exhibit 2-2. The formal charge on carbon (C) is ______.ANS:−1

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Chapter 2314.Refer to Exhibit 2-2. The formal charge on oxygen (D) is ______.ANS:+1Exhibit 2-3Phenylalanine is an amino acid that is essential to human nutrition. The representation belowshows the structure of phenylalanine at physiological pH. Consider this structure to answerthe following question(s).5.Refer to Exhibit 2-3. Assign any formal charges to atoms in this representation ofphenylalanine.ANS:16.Refer to Exhibit 2-3. The oxygen atom labeledA. has ______ non-bonding electrons.ANS:four17.Refer to Exhibit 2-3. The oxygen atom labeledB. has _____ bonding electrons.ANS:two

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Polar Covalent Bonds: Acids and Bases4Exhibit 2-4Use theconvention and the crossed arrowto show the direction of the expectedpolarity of the indicated bonds in the following compounds.18.Refer to Exhibit 2-4. The C−F bond in fluorobenzene,ANS:19.Refer to Exhibit 2-4. The C−Si bond in tetramethylsilane, (CH3)4SiANS:20.Refer to Exhibit 2-4. The C−O bond in furan,ANS:Exhibit 2-5Label the acid, conjugate acid, base, and conjugate base in each reaction below.21.ANS:

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Chapter 2522.ANS:Exhibit 2-6Refer to the following equation to answer the question(s) below. Place the letter corresponding tothe correct answer in the blank.23.Refer to Exhibit 2-6. The strongest Brønsted-Lowry acid in the equation is ______.ANS:D24.Refer to Exhibit 2-6. The strongest Brønsted-Lowry base in the equation is ______.ANS:C25.Refer to Exhibit 2-6. Will this reaction take place as written? Explain.ANS:No, the reaction will not take place as written because the strongest acid reacts with the strongestbase to give the weakest conjugate acid and the weakest conjugate base.D(pKa= 15.7) is astronger acid thanA(pKa= 18).26.An acid with a low pKa:a.is a weak acidb.is a strong acidc.has a weak conjugate based.both b and cANS:d

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