Solution Manual For Organic Chemistry: A Guided Inquiry, 2nd Edition

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ChemActivity 1: Bond Angles and Shape(What are the bond angles and shape of CH4?)Model 1: Planetary Model of an AtomIn a planetary model of an atom,negatively charged electrons(–1 each) are arranged around apositively charged nucleus(+Z= nuclear charge) in a series ofshellsthat look like orbits.+1= electron+6+7+8+9+10HCNOFNeshell #1shell #2Figure 1.1: Valence Shell Representations of Hydrogen, Carbon, Nitrogen, Oxygen, Fluorine, and Neoncore electrons= electrons in any inner shell(s) (don’t participate in bonding)core atom= the nucleus (made up of protons and neutrons) plus the core electronsvalence electrons= electrons in the outermost shell (participate in bonding)valence shell= outermost shell, where valence electrons are foundElectronsDO NOT“orbit” the nucleus like the planets orbit the sun. In ChemActivity 3 we will study a more complex modelin which electrons are described as inhabiting 3-dimensional regions of space called “orbitals” (1s, 2s, 2px, 2py, 2pz, 3s, etc.).Critical Thinking Questions1.(E) What does the number (+Z) at the center of each atom in Figure 1.1 represent, and whatnumber would you expect at the center of a representation of a bromine atom (Br)?2.(E) How many total electrons does an oxygen atom have, and how could you find the answer tothis using a periodic table?3.(E) How many valence electrons does each atom in Figure 1.1 have, and what number on aperiodic table gives you these answers?4.What is the maximum number of electrons that can fit in…a.(E) shell No. 1?b.(E) shell No. 2 (Neon has a full Shell No. 2)?c.Describe how the answers to a) and b) are contained in the structure of the periodic table.

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ChemActivity 1: Bond Angles and Shape9Model 2: Bonding and Non-bonding Electron DomainsBonding electron domain= shared valence electrons (2, 4, or 6e—) localized between two core atoms3 typesÆSingle Bond(1 pair, 2 electrons);Double Bond(2 pairs, 4 e—);Triple Bond(3 pairs, 6 e—)Non-bonding electron domain(“lone pair”) = pair of valence electrons (2 e—)notinvolved in a bondOne way to think of abond:two positively charged core atoms mutually attracted to the negativelycharged electrons that are localized between them.+8valence shellrepresentation*dot shorthandelectron domainbond-lineball & stickspace fillingHHOONN+1+1+8+7+7OONNHHHHOONNFigure 1.2: Example of a Single, Double, and Triple BondCritical Thinking Questions5.(E) How many electrons are in a triple bond?6.(E) Identify eachlone pairshown in the first four rows of Figure 1.2.7.(E) Each molecule in Figure 1.2 has exactly onebonding electron domain. Identify it and…a.label whattypeof bonding electron domain it is.b.report the number of electrons in each bonding electron domain.8.You hear a student from a nearby group say that “Electron domains repel one another.” Citeevidence from Figure 1.2 to support or refute this statement.

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10ChemActivity 1: Bond Angles and ShapeModel 3:Bond Anglesbond angle= angle defined by any three atoms in a molecule. (e.g.,∠HBH in BH3, below)According to the Valence Shell Electron Pair Repulsion model (VSEPR)electron domains spread outas far as possiblefrom one another (repel one another).Even for a molecule with different-sized electron domains (e.g., H2CO), bond angles remain very closeto those you would expect if all the electron domains were the same size.Table 1.1: Bond Angles of Selected MoleculesBond-line StructureApproximate Bond AngleH—Be—HNCHOCO180BHHHCHHCOHHCHHH120Critical Thinking Questions9.Use VSEPR to explain why the∠HBH bond angle of BH3is 120o. (Hint: What is one-third of360o?)10.Both the∠HCH and∠HCO bond angles of H2CO (formaldehyde)are very close to 120o, but oneis slightly smaller than the other. Predict which is smaller, and explain your reasoning.11.Use VSEPR to assign a value of “close to 180o” or “close to 120o” to each bond angle markedwith a dotted line. (These angles are drawn as either 90oor 180o, but may be another value.)HCCCNHHCCCHHHHNCOHHCHOHCCCHHHHH12.Consider the followingflatdrawing of methane (CH4).a.What is∠HCH bond angle implied by this drawingif you assume it is flat?b.Are the electron domains of this flat CH4spread out as much as possible?CHHHHc.Use model materials tomake a model of CH4(methane). If you assembled it correctly, thefour bonds (bonding electron domains) of your model will be 109.5oapart.d.In which representation,the drawing aboveorthe model in your hand(circle one) are theH’s of CH4more spread out around the central carbon?

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ChemActivity 1: Bond Angles and Shape11e.Confirm that your model looks like the following drawing. Thewedgebondrepresents a bond coming out of the page, and thedash bondrepresents a bond going into the page.HCHHHf.You will often see methane drawn as if it were flat (like on the previous page). Why is thismisleading, and what is left to the viewer’s imagination when looking at such a drawing?13.Use VSEPR to assign a value of (close to) 109.5, 180 or 120 to each markedbond angle.CCCHHHHNHCHCHHOOHHNCHOCHHHHHHOCHHHH14.A student draws the picture ofammonia(NH3) in the box below, left, and predicts it will be a flatmolecule with∠HNH bond angles of exactly 120o. Unfortunately, the student left something out.NHHH120oNHHHlone pair in non-bonding domainStudent's incorrectdrawingAccurate Representation of Ammoniaa.What did the student omit from his drawing?b.What is the actual∠HNH bond angle of ammonia (based on the drawing above, right)?c.Explain why water, ammonia, and methane (shown below) all have about the same bondangles (close to 109.5o) even though they have different numbers of bonds.HOHNHHHHCHHHwaterammoniamethaneMemorization Task 1.1: Correlation between #No. of Electron Domains and Bond AngleElectron Domains(bonding + non-bonding)Bond Angle Close To…Examples4109.5oCH4, NH3, H2O, H4N+3120oBH3, H3C+, CH2, H2CO2180oBeH2, O2N+, CO2, HCN

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12ChemActivity 1: Bond Angles and ShapeModel 4:ShapeAcentral atom= anatom bonded to two or more other atoms. (e.g., Oxygen in H—O—H)Eachcentral atomhas ashapedetermined by the arrangement of theatomsattached to it.Memorization Task 1.2: The five molecular shapes we will encounter in this courseHCHHHtetrahedralNHHHC atom inthe centeris not acornerpyramidalOCOlinearHOHbentCHOHtrigonalplanardotted line (---) showsedges that are NOT bondsCritical Thinking Questions15.(E) Explain why the molecule H—F is not associated with an official shape as defined in Model 4.16.How many central atoms does the molecule H2NCH3have, and what is the shape about each?NHHCHHH17.Indicate the bond angle and shape about each central atom.CHHFOHHCCHHOOHHNHHHHHHHCHHH18.Explain how there can be two kinds of bent: “bent-109.5o” and “bent-120o,” and give an exampleof each from the previous question. (Note that “bent-109.5o” is more common than “bent-120o.”)19.A student makes the following statement: “The shape of water istetrahedralbecause the fourelectron pairs about oxygen are approximately 109.5oapart and point to the corners of atetrahedron.” What misconception does this statement convey?20.A student who missed this class needs to know how to predict the bond angles and shape of amolecule from looking at its bond-line representation. Write a concise but complete explanationfor this student.

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ChemActivity 1: Bond Angles and Shape13Exercises1.Draw a valence shell representation of aa.Helium atom.b.Sulfur atom.2.In the box, draw abond-linerepresentationof the molecule shown on the left. Be sure to includeonlyvalence electrons (either as line bonds or lone pairs).+8+1+6+7+1+1+1line-bond rep.+1+13.Consider the incomplete valence shell representation below.a.Assume the atom is neutral, and write the correct nuclear charge at the center of the atom.b.What is the identity of this neutral atom?4.How many valence electrons does a neutrala.K atom have?b.C atom? N atom? O atom?5.Consider the molecules AlCl3(aluminum chloride) and CF4(carbon tetrafluoride).a.Draw the valence shell representation of each.b.Predict the value of the XYX bond angle, and explain your reasoning.6.Draw an example of a bent molecule with a bond angle of near 109.5o; then draw a different bentmolecule with a bond angle of about 120o.

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14ChemActivity 1: Bond Angles and Shape7.Label each atom marked with an arrow with the appropriateshape name,andestimate the bondangles around itas being close to one of 180o, 120o, 109.5oor 90o. (circled charges indicate thecharge on the molecule or fragment)CHHFOHHHNHHOOHHNHHHH8.Make a model of each of the following molecules:HOClClCClClHHOClHHClCClClHHCOHHHHNCOOHHCCHHHHCCCCCHHHHHHHHHHCCCOHHHHHHHOa.Based on your model, draw a bond-line representation with as many atoms as possible in theplane of the paper. Use wedge and dash bonds to represent any atoms that do not lie in theplane of the paper.b.Indicate each unique bond angle and the shape of each unique central atom.9.Read the assigned pages in the text, and do the assigned problems.Using “The Big Picture” & “Common Points of Confusion” SectionsIt can be fun to “discover” your own answers as you are asked to do in this workbook, but…How do you know if your “discovered” understanding is valid?The answer is: Even practicing scientists and professors never knowfor surethat they are correct. Insome ways, deciding if you are right is the hardest part of being a scientist. A practicing scientist cannot“check the key” to see if her new theory is correct! In this course and in real life you must constantlytest and improve your current understanding by applying it to problems and discussing it with peers.One goal of this course is to develop the ability to recognize the signs when you are correct; and equallyimportantly, recognize the signs when you are missing something critical.After completing a ChemActivity, one way to start checking your understanding is to read the BigPicture and Common Points of Confusion sections (examples on the next page). If the homework orthese sections do not make sense to you then you are missing something important. You need to goback and study the activity, do more problems, read the textbook more closely, or seek help from apeer, teaching assistant or your instructor. (More advice about how to know if you are “learning theright thing” can be found in the “To the Student” section the precedes the Table of Contents for thisbook, and the Frequently Asked Questions section of the IntroActivity that precedes this chapter.)

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ChemActivity 1: Bond Angles and Shape15The Big PictureAfter this week you will rarely be asked to report a bond angle or shape. Yet it is critical that you beable to do both. Doing well in organic chemistry largely depends on your ability to see molecules asthree-dimensional objects. The electrons of most every central atom you will encounter are arranged109.5oor 120oapart (180oarrangements are quite rare), but it gets complex when you are expected tosee a molecule with multiple central atoms in 3D. The purpose of this activity is to get you startedthinking about tetrahedral and trigonal planar geometries. If you do not already have a model set,borrow or purchase one. You will need it for the first half of this course while you are “programming”your brain to see the two-dimensional drawings on the page as 3D objects.Common Points of ConfusionAt the end of each chapter you will find a brief explanation of common student misconceptions. Thissection may be useful if a homework problem does not make sense or as final preparation for a quiz.•When asked the question, “What is theshapeof water?” students sometimes answer “tetrahedral”because they know that the fourelectron domainsof water spread out into a tetrahedral-typepattern. However, the answer is “bent” because shape is determined by the location of theatoms.Similarly, it makes no sense to ask what is the bond angle between the two lone pairs of water—there should be approximately 109.5obetween these lone pairs, but this is difficult to measure.•Some students mistakenly assume they are expected to predict the EXACTbond angleof a givenmolecule. Generally, you are expected to predict only if the bond angle is closest to 180, 120, or109.5 degrees.

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ChemActivity 2: Lewis Structures(How do I draw a legitimate Lewis structure?)Model 1: G. N. Lewis’ Octet RuleIn the early part of the last century, a chemist at the University of California at Berkeley named GilbertN. Lewis devised a system for diagramming atoms and molecules. Though simple, the system is stillused today because predictions made from these diagrams often match those based on experiment.Lewisproposed the following representations for the first ten elements with theirvalence electrons.HLiBeBCNOFNeHeFigure 2.1: Electron Dot Representations of ElementsOnly He and Ne are found in nature as shown above. All the other elements are found either as acharged species (ion) or as part of amoleculethat can be represented as a legitimateLewis structure.CHECKLIST: a LegitimateLewis Structure is a dot or line bond representation in which…I.The correct TOTAL number of valence electrons is shown.II.The sum of the valence electrons around each hydrogen atom is two.III.The sum of the valence electrons (bonding pairs + lone pairs) around eachcarbon, nitrogen,oxygen, or fluorine atom is eight–anoctet. (this is the“octet rule”)Note that Lewis’ rules apply to H, C, N, O and F. We will find that atoms in the next row of the periodic table (e.g., silicon,phosphorus, and sulfur) and beyond commonly violate the octet rule.OHHOHHOH="lone pair""bondingpair"we will usually useline-bond structuresoxygen atom+O=oxygen atom+2 electronsO-2wateroxygen -2 anionHFF=2 fluorine atomsFF2(fluorine gas)FFF-1-12 hydrogenatomsFigure 2.2: Examples of combinations that form legitimate Lewis structuresRead this page once, and begin answering the Critical Thinking Questions on the next page.

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ChemActivity 2: Lewis Structures17+8+1+1+7+1+1+1+9+1NHHHOHHFShellLewisHFigure 2.3: Valence Shell and Lewis Representations of Selected CompoundsCritical Thinking Questions1.(E) Confirm that each molecule or ion in Figures 2.2 and 2.3 is a legitimate Lewis structure.2.Thevalence shellof an atom in a legitimate Lewis structure (seeFigure 2.3) has what in commonwith the valence shell of a noble gas? (Noble gases are stable elements found in the last column ofthe periodic table, e.g., He, Ne, Ar, etc.)3.Draw ashell representation and Lewis structurefortheionof fluorine that you predict is most likely tobe stable, and explain your reasoning.4.Draw aLewis structureof a neutral molecule thatyou expect to be a stable and naturally occurringcombination ofone carbon atomand some numberof fluorine atoms.5.The following structure isNOTa legitimate Lewis structure of a neutral O2molecule.a.Explain why it is not legitimate.OOb.Which item on the legitimate Lewis structure CHECKLIST in Model 1 is violated?6.It is impossible to draw a legitimate Lewis structure of a neutral NH4molecule. Hypothetically,how many valence electrons would such a neutral NH4molecule haveif it could exist?a.The +1 cation, NH4+, does exist.How many valence electrons does one NH4+ion have?b.Draw the Lewis structure for NH4+7.Describe how to calculate the total number of valence electrons in a +1 ion, in a -1 ion.

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18ChemActivity 2: Lewis StructuresModel 2: Two Lewis Structures for CO2OCOOCOIIIExperiments indicate that both carbon-oxygen bonds ofcarbon dioxide (CO2) are identical.Critical Thinking Questions8.(E) Are both structures of carbon dioxide (CO2) in Model 2 legitimate Lewis structures?9.(E) Which Lewis structure best fits experiments indicating that both C to O bonds are identical?Model 3:Formal ChargeOne of the Lewis structures of CO2in Model 2 is less favored because it has an imbalance of charge. Tofind the “hot spots” of + and – charge in a structure we must calculate the formal chargeof each atom.Memorization Task 2.1: Formal Charge = (Group Number) – (no. lines) – (no. dots)•Group Number= Column number on the periodic table (or number of dots on atom in Fig. 2.1)•No. lines= Number of line bonds to the atom in the structure•No. dots= Number of non-bonded electrons on an atom in the structureCritical Thinking Questions10.(E) According to the periodic table at the end of this book, what is theGroup Numberof nitrogen?a.(Check your work.) Does this match the number of dots on N in Fig. 2.1?b.(E) How many line bonds are attached to N on the structure of NH3?c.(E) How many nonbonded electrons are drawn on N in NH3?d.Calculate the formal charge of each atom in NH3?NHHH11.(Check your work.) Most atoms in organicmolecules (including all atoms of NH3) haveazero formal charge. Confirm that eachatom at right has a zero formal charge.CHHHHOHHBrHHCHOCNH12.In this course we will often encounter+1 and -1 formal charges, though rarely will we see formalcharges of +2, -2, +3, -3, etc., because they are generally unfavorable. By convention,only nonzeroformal charges are shown on a structure. Plus 1 and minus 1 formal charges are shown as a + or–or as a circled + or – (/). Confirm the formal charge assignments below.NCHHHHOHCHHCHCHCCCHCHHHHHCl

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ChemActivity 2: Lewis Structures1913.A complete Lewis structure must show all nonzero formal charges. Complete each of thefollowing Lewis structures by adding anymissingformal charges.HCOOSHHOOHHNHHPCHHCCCHOCOCNNCOH3CCOCHNNHHHHHHHHHHHHHHCHHHHHHH14.Net Charge= total charge on a molecule. (Check your work.) Structures in the top row of theprevious question have a net charge of +1, structures in the middle row have a net charge of zero,and structures in the bottom row have a net charge of -1.15.T or F: The sum of the formal charges on a Lewis structure is equal to the net charge on themolecule or ion. (If false, give an example from CTQ 13 that demonstrates this is false.)16.T or F: If the net charge on a molecule is zero, the formal charge on every atom in the moleculemust equal zero. (If false, give an example from CTQ 13 that demonstrates this is false.)17.Identify theoneLewis structure in CTQ 13 that is NOT legitimate, and explain what attribute of alegitimate Lewis structure it is missing.(Check your work.)The top-center Lewis structure in CTQ 13 is akey exception to the octet rulecalled a carbocation.We will study carbocations extensively in the course. For reasons we will discusslater, a carbocation carbon rarely is involved in a double or triple bond. That is, a carbocation almostalways has three single bonds, as shown on the next page.Model 4:Condensed Structuresand Using R, X, & Z as PlaceholdersR, X,andZare not elements but placeholders for atoms or groups of atoms. For example, ethanol…CHOCHHHHHcan bewrittenas...ROHwhere...R =CHCHHHHHOCH2CH3HOR-CH2CH3ethanolan "ethyl" groupgeneral structure for an alcoholCondensed Structuresgive just enoughinformation to draw thestructure

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20ChemActivity 2: Lewis StructuresMemorization Task 2.2: Conventions for the use ofR, X,andZas placeholders•Ris used to represent H or analkyl group.An alkyl group is a straight or branched chainmade from C and H atoms with formula CnHme.g., -CH3, -CH2CH3, -C(CH3)3, etc.•Xis used to represent F, Cl, Br, or I (the common “halogens”)•Zwill be used to representanyatom or group of atomsIf the identity ofR, X,orZis not specified, assume a wide range of legal identities are possible.For example: in the table below, the formal charges shown hold true regardless of the identities ofZ.Model 5: RecognizingFormal Chargesfor C, N, O, and X+10−1CZZZNote: The two other ways to draw acarbocation are very uncommon.CZZZZZCZZCZZZCZCZZZZCZCZCNZNZZNZfour ways (draw the two that are missing)draw three waysdraw two waysOdraw three waysdraw two waysdraw one wayZXZXZtwo ways (less common)draw one waydraw one way (an anionic atom)XCritical Thinking Questions18.Complete the box in Model 5 for N+1, by drawing theothertwo ways an N can carry a +1 formalcharge. (Hint: These two structures should have molecular formulas+NZ4, and+NZ3, respectively.)19.Complete the rest of the table for N, O or X by drawing the number of Lewis structures specified.20.For a legitimate Lewis structure…a.What is the formal charge ofanynitrogen with four bonds? … three bonds? … two bonds?b.What is the formal charge ofanyoxygen with three bonds? … two bonds? … one bond?c.What is the formal charge ofanyhalogen (X) with two bonds? … one bond? … zero bonds?21.Parts a-c in the previous CTQ mean you can quickly recognize the formal charge on an N, O and Xwithout considering non-bonded electrons (dots). Explain why a similar statement equating formalcharge and number of bonds DOES NOT WORKfor carbon(i.e., you have to look for the dots).

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ChemActivity 2: Lewis Structures21Memorization in Organic Chemistry:Memorization is a small but important part of learning organic chemistry.Memorization Taskssuch asthe one below will be clearly marked throughout this book. This is done to encourage you to memorizethe critical bits of informationinthese boxes AND help you realize that you can derive everythingoutsideof these boxes from the key concepts in the ChemActivity.Memorization Task 2.3: Corrleation between No. of bonds and formal charge for C, N, O, XBefore the next class: Study the patterns in Model 5, and do practice problems until you can QUICKLYrecognize the formal charge (+1, 0, or -1) of any C, N, O or X in a structure without counting.For example, an N with four bonds should look “wrong” without a +1 formal charge; and an N with twobonds should look “wrong” without a -1 formal charge. (Write a similar rule for oxygen!)Note that for carbon you must count the number of bondsAND check whether there is a lone pair on C.That is, a C with three bonds and no lone pair should look “wrong” without +1 formal charge; and a Cwith three bonds and one lone pair should look “wrong” without a -1 formal charge.Exercises1.Make a checklist that can be used to determine if a Lewis structure is correct and that it is the bestLewis structure.2.Turn back to Model 2, and add any missing formal charges to each Lewis structure of CO2.a.Based on the concept of formal charge, which is the better Lewis structure for CO2(inModel 2), Lewis structure IorLewis structure II? Circle one, and explain your reasoning.b.Is your choice consistent with the experimental data?3.Shown below are two possible Lewis structures for the amino acid called glycine.HNHCCHHOOHStructure IHNHCCHHOOHStructure IIa.Predict the∠COH bond angle based on the Lewis structure on the left.b.Predict the∠COH bond angle based on the Lewis structure on the right.c.Which prediction do you expect to be more accurate? Explain your reasoning.4.Draw the Lewis structure of a neutral molecule that is a naturally occurring combination ofhydrogen atomsand one sulfur atom. What is the shape of this molecule?

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22ChemActivity 2: Lewis Structures5.Draw legitimate Lewis structures of the following species, and predict the geometry about thecentral atom (shape).+b.NOc.Na.NH322O (try with N or Oas the central atom)2−d.CCle.CO43f.N2(Note: based on the definition, a molecule with only two atoms does not have a shape.)6.For each element, predict (and draw a Lewis structure of) the most commonly occurring ion(some of these have a charge greater than +/- 1)a.sulfurc.magnesiumb.iodined.oxygen7.Predict which of the following species is least likely to exist.+−NOCHHO22−8.The molecules BH3and SF6and the ion SO4exist and are stable. Draw a Lewis structure of each,and comment on whether they are exceptions to Lewis’ octet rule.9.These are NOTlegitimate Lewisstructures (and aremissing formalcharges). Show (as inthe example) how apair of electrons canbe moved to make theLewis structurelegitimate.NOOOH(curved arrow showswhere the electron pairwas moved from and to)legitimate Lewis structureHNCHHONNCHHHHFOOHHNCHHO10.Fill in missing formal charges where needed (all lone pairs are shown).a)b)c)NOOOCHHHd)e)f)NHHHHCHHHCOOHNNNHCSSCS2CH3–NO3–NH4+CH3COOHHN3

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