SOLUTIONS MANUAL Jan William Simek ORGANIC CHEMISTRY L.G.Wade,Jr
TABLE OF CONTENTS Preface... Symbols and Abbreviations. Introduction and Review. 1 Chapter 2 Structure and Properties of Organic Molecules 25 Chapter 3 Structure and Stereochemistry of Alkanes... .45 Chapter 4 The Study of Chemical Reactions...... 59 Chapter 5 Stereochemistry 70 Chapter 6 Alkyl Halides:Nucleophilic Substitution and Elimination.... .99 Chapter 7 Structure and Synthesis of Alkenes. 135 Chapter 8 Reactions of Alkenes............ ..159 Chapter 9 Alkynes........ 191 Chapter 10 Structure and Synthesis of Alcohols... .211 Chapter 11 Reactions of Alcohols 229 Chapter 12 Infrared Spectroscopy and Mass Spectrometry. 259 Chapter 13 Nuclear Magnetic Resonance Spectroscopy .271 Chapter 14 Ethers,Epoxides,and Sulfides... 299 Chapter 15 Conjugated Systems,Orbital Symmetry,and Ultraviolet Spectroscopy... .317 Chapter 16 Aromatic Compounds. 341 Chapter 17 Reactions of Aromatic Compounds... .365 Chapter 18 Ketones and Chapter 19 Amines. .439 Chapter 20 Carboxylic Acids..... 469 Chapter 21 Carboxylic Acid Derivatives... 499 Chapter 22 Condensations and Alpha Substitutions of Carbonyl Compounds Chapter 23 Carbohydrates and Nucleic Acids.... .585 Chapter24 Amino Acids,Peptides,and Proteins .617 Chapter 25 Lipids. 645 Chapter26 Synthetic Polymers. .659 Appendix 1:Summary of IUPAC Nomenclature.... ....675 Appendix 2:Summary of Acidity and Basicity 689
TABLE OF CONTENTS Preface ........................................................................................................................................ v Symbols and Abbreviations ...................................................................................................... vii Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Appendix I: Appendix 2: Introduction and Review ..... . ....... . ... . ................ . ....... ................. . .............. ............ 1 Structure and Properties of Organic Molecules .................................................. 25 Structure and Stereochemistry of Alkanes .................................... ...................... 45 The Study of Chemical Reactions . . . ...................... ............................................. 59 Stereochemistry .... . .............. . ...... ................................ . ........ . ............................. 79 Alkyl Halides: Nucleophilic Substitution and Elimination ................. . ....... ....... 99 Structure and Synthesis of Alkenes ... . ..... . ........ . . .............................................. 135 Reactions of Alkenes ... . ......... ... ....... . . .............................................................. 159 Alkynes ...... . . ........................ . .............................................. . ................. .......... 191 Structure and Synthesis of Alcohols .............. ....................... . .... . ...................... 211 Reactions of Alcohols .................. . ................................ ............ ............ ........... 229 Infrared Spectroscopy and Mass Spectrometry ........ . ............ ................ . ...... ..... 259 Nuclear Magnetic Resonance Spectroscopy ....... . . ............................ . .... . . ... ...... 271 Ethers, Epoxides, and Sulfides ................................. . .......... ............................. 299 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy ............ 317 Aromatic Compounds ...... ................. . ........................... ................................... 341 Reactions of Aromatic Compounds ............................................ ......... . ............ 365 Ketones and Aldehydes .............. .... . ................. ............................. .................. 401 Amines .................. . .... ... ........... ....................................................................... 439 Carboxylic Acids ............................................................................................. 469 Carboxylic Acid Derivatives ...................................................... ...................... 499 Condensations and Alpha Substitutions of Carbonyl Compounds ... . ... . . ........... 537 Carbohydrates and Nucleic Acids ................................ . ........ ........ ................... 585 Amino Acids, Peptides, and Proteins ................................................... ............ 617 Lipids ... . ................................................... . ...................................................... 645 Synthetic Polymers . ... . ..... . . ............... . ........... .......... . ....... ................................. 659 Summary of IUPAC Nomenclature ... . ........ .......... . ................. .......... ................ 675 Summary of Acidity and Basicity ...... ........................... .................. . ... . ............ 689 iii
PREEACE Hints for Passing Organic Chemistry Do you want to pass your course in organic chemistry?Here is my best advice,based on over the easy way out unti the cover there is no shor-cu onless you ha a measure ed IQ them,you will u want your n coming to y your pend ectomy e pre answ before and st galing with e m pndmDyprioming.emr primary goa oing th ese proble is not just getting the righ er,but understanding the Hint#2:Keep up.Getting behind in your work in a course that moves as quickly as this one is the Kiss of Deatl an study all of the ma erial the pass.Study organic chemistry like a foreign language:try to do some every day so that the freshly- trained Use your teacher's office hours when you have ifficuy Many choos (n which orgnic chemistry ar offering).Here's a secret a: tely the st way to each in your brain ith wen f you th problems,youwil gain great insight into what this is all about. Purpose of this Solutions Manual t is the point of this Solutions Manual?First,I can't do your studying for you. 可c2 m Second essor Wac Professor Kantoro wski (my reviewer).and ve gone re that wna ovide degree of rigor:beyond the fundamental requirement of correctness.I have tried to flesh out thes te but su 3)provide insight into how olve a problem and into where the understand where students have touble s have tried to anticipate detail sh concept.as well as the ans more human han othe am hun students m are mistakes in can and this bo it in the am PLEASE let me know so that it can be corrected What's New in this edition? s he clarify how to arr notec The IUP appendix has been expanded to include bicyclics,heteroatom graphics！The nmevrmiettythre-dimeio tury ve adde rudime
PREFACE Hints for Passing Organic Chemistry Do you want to pass your course in organic chemistry? Here is my best advice, based on over thirty years of observing students learning organic chemistry: Hint #1: Do the problems. It seems straightforward, but humans, including students, try to take the easy way out until they discover there is no short-cut. Unless you have a measured IQ above 200 and comfortably cruise in the top 1 % of your class, do the problems. Usually your teacher (professor or teaching assistant) will recommend certain ones; try to do all those recommended. If you do half of them, you will be half-prepared at test time. (Do you want your surgeon coming to your appendectomy having practiced only hal/the procedure?) And when you do the problems, keep this Solutions Manual CLOSED. A void looking at my answer before you write your answer-your trying and struggling with the problem is the most valuable part of the problem. Discovery is a major part of learning. Remember that the primary goal of doing these problems is not just getting the right answer, but understanding the material well enough to get right answers to the questions you haven't seen yet. Hint #2: Keep up. Getting behind in your work in a course that moves as quickly as this one is the Kiss of Death. For most students, organic chemistry is the most rigorous intellectual challenge they have faced so far in their studies. Some are taken by surprise at the diligence it requires. Don't think that you can study all of the material the couple of days before the exam -well, you can, but you won't pass. Study organic chemistry like a foreign language: try to do some every day so that the freshlytrained neurons stay sharp. Hint #3: Get help when you need it. Use your teacher's office hours when you have difficulty. Many schools have tutoring centers (in which organic chemistry is a popular offering). Here's a secret: absolutely the best way to cement this material in your brain is to get together with a few of your fellow students and make up problems for each other, then correct and discuss them. When you write the problems, you will gain great insight into what this is all about. Purpose of this Solutions Manual So w hat is the point of this Solutions Manual? First, I can't do your studying for you. Second, since I am not leaning over your shoulder as you write your answers, I can't give you direct feedback on what you write and think-the print medium is limited in its usefulness. What I can do for you is: I) provide correct answers; the publishers, Professor Wade, Professor Kantorowski (my reviewer), and I have gone to great lengths to assure that what I have written is correct, for we all understand how it can shake a student's confidence to discover that the answer book flubbed up; 2) provide a considerable degree of rigor; beyond the fundamental requirement of correctness, I have tried to flesh out these answers, being complete but succinct; 3) provide insight into how to solve a problem and into where the sticky intellectual points are. Insight is the toughest to accomplish, but over the years, I have come to understand where students have trouble, so I have tried to anticipate your questions and to add enough detail so that the concept, as well as the answer, is clear. It is difficult for students to understand or acknowledge that their teachers are human (some are more human than others). Since I am human (despite what my students might report), I can and do make mistakes. If there are mistakes in this book, they are my sole responsibility, and I am sorry. If you find one, PLEASE let me know so that it can be corrected in future printings. Nip it in the bud. What's New in this edition? Better answers! Part of my goal in this edition has been to add more explanatory material to clarify how to arrive at the answer. The possibility of more than one answer to a problem has been noted. The IUPAC Nomenclature appendix has been expanded to include bicyclics, heteroatom replacements, and the Cahn-Ingold-Prelog system of stereochemical designation. Better graphics! The print medium is very limited in its ability to convey three-dimensional structural i�formation, . a problem that has plagued organic chemists for over a century. I have added some graphiCS created 1I1 the software, Chem3D®, to try to show atoms in space where that information is a key part of the solution. In drawing NMR spectra, representational line drawings have replaced rudimentary attempts at drawing peaks from previous editions. Better jokes? Too much to hope for. v
Some Web Stuff Acknowledgments ct of this scope is ever done alone.These are team efforts.and there are several people who havd and facilitated n n fashion antho deserve my thanks le person. He has gone to Hene olmytnd commenon myee have w colleague,Dr.Eric Kantorows Dr.Kristen Meisenheimer,and Dr.Dan Mattern. Mr.Richard King has offered numerous suggestions on how I am grade to them al Good hooks would not exis withoutther dedication.profession and experience Among the man ople who contributed The entire manuscript was produced using ChemDr the remarkable software for drawing ridge,MA.W re n oodm ny y u Lang who su a Jan William Sirek CaPoly State Univers and Biochemistry 3407 DEDICATION To my inspirational chemistry teachers Joe Plaskas,who made the batter Kurt Kaufman,who baked the cake; Carl Dierassi,who put on the icing: and to my parents: Ervin J.and Imilda B.Simek. who had the original concept
Some Web Stuff Prentice-Hall maintains a w eb site dedicated to the Wade text: try www.prenhall.com/wade. Two essential web sites providing spectra are listed on the bottom of p. 270. Acknowledgments No project of this scope is ever done alone. These are team efforts, and there are several people who have assisted and facilitated in one fashion or another who deserve my thanks. Professor L. G. Wade, Jr., your textbook author, is a remarkable person. He has gone to extraordinary lengths to make the textbook as clear, organized, informative and insightful as possible. He has solicited and followed my suggestions on his text, and his comments on my solutions have been perceptive and valuable. We agreed early on that our primary goal is to help the students learn a fascinating and challenging subject, and all of our efforts have been directed toward that goal. I have appreciated our collaboration. My new colleague, Dr. Eric Kantorowski, has reviewed the entire manuscript for accuracy and style. His diligence, attention to detail and chemical wisdom have made this a better manual. Eric stands on the shoulders of previous reviewers who scoured earlier editions for errors: Jessica Gilman, Dr. Kristen Meisenheimer, and Dr. Dan Mattern. Mr. Richard King has offered numerous suggestions on how to clarify murky explanations. I am grateful to them all. The people at Prentice-Hall have made this project possible. Good books would not exist without their dedication, professionalism, and experience. Among the many people who contributed are: Lee Englander, who connected me with this project; Nicole Fo1chetti, Advanced Chemistry Editor; and Kristen Kaiser and Carole Snyder, Project Managers. The entire manuscript was produced using ChemDraw®, the remarkable software for drawing chemical structures developed by CambridgeSoft Corp., Cambridge, MA. We, the users of sophisticated software like ChemDraw, are the beneficiaries of the intelligence and creativity of the people in the computer industry. We are fortunate that they are so smart. Finally, I appreciate my friends who supported me throughout this project, most notably my good friend of almost forty years, Judy Lang. The students are too numerous to list, but it is for them that all this happens. Jan William Simek Department of Chemistry and Biochemistry Cal Poly State University San Luis Obispo, CA 93407 Email: jsimek@calpoly.edu DEDICATION To my inspirational chemistry teachers: Joe Plaskas, who made the batter; Kurt Kaufman, who baked the cake; Carl Djerassi, who put on the icing; and to my parents: Ervin J. and Imilda B. Simek, who had the original concept. vi
SYMBOLS AND ABBREVIATIONS Below is a list of symbols and abbreviations used in this solutions manual c with those used in the etoo by Wade.Dont of these tomake sense toyouou m them throughout your study of organic chemistry.) BONDS a single bond a double bond a triple bond a bond in three dimensions,coming out of the paper toward the reader a bond in three dimensions,going behind the paper away from the reader a stretched bond,in the process of forming or breaking ARROWS in a reaction,shows direction from reactants to products signifies equilibrium (not to be confused with resonance) signifies resonance(not to be confused with equilibrium) the arrowhead with two barbs shows movement of a pair of electrons 十一 shows polarity of a bond or molecule,the arrowhead signifying the more negative end of the dipole SUBSTITUENT GROUPS Me a methyl group.CH3 an ethyl group,CH2CH a propyl group,a three carbon group(two possible arrangements) a butyl group.a four carbon group(four possible arrangements) R the general abbreviation for an alkyl group (or any substituent group not under scrutiny) a phenyl group,the name of a benzene ring as a substituent,represented: or N the general name for an aromatic group continued on next page vii
SYMBOLS AND ABBREVIA TIONS Below is a list of symbols and abbreviations used in this Solutions Manual, consistent with those used in the textbook by Wade. (Do not expect all of these to make sense to you now. You will learn them throughout your study of organic chemistry.) BONDS - 111111111111 ARROWS - .. .. a single bond a double bond a triple bond a bond in three dimensions, coming out of the paper toward the reader a bond in three dimensions, going behind the paper away from the reader a stretched bond, in the process of forming or breaking in a reaction, shows direction from reactants to products signifies equilibrium (not to be confused with resonance) signifies resonance (not to be confused with equilibrium) shows direction of electron movement: the arrowhead with one barb shows movement of one electron; the arrowhead with two barbs shows movement of a pair of electrons shows polarity of a bond or molecule, the arrowhead signifying the more negative end of the dipole SUBSTITUENT GROUPS Me a methyl group, CH3 Et an ethyl group, CH2CH3 Pr a propyl group, a three carbon group (two possible arrangements) Bu a butyl group, a four carbon group (four possible arrangements) R the general abbreviation for an alkyl group (or any substituent group not under scrutiny) Ph a phenyl group, the name of a benzene ring as a substituent, represented: < » or Ar the general name for an aromatic group continued on next page 0- vii
Symbols and Abbreviations.continued SUBSTITUENT GROUPS.continued an acetyl group: CH3-C- 9 a cyclohexyl group: oonroup:cH一《-含力 Ts 0 Boc REAGENTS AND SOLVENTS DCC dicyclohexylcarbodiimide 〉N=C=N〈 DMSO dimethylsulfoxide CH ether diethyl ether,CH3CH2OCH2CH3 MCPBA meta-chloroperoxybenzoic acid -0-0H MVK methyl vinyl ketone NBS N-bromosuccinimide continued on next page vi
Symbols and Abbreviations, continued SUBSTITUENT GROUPS, continued o II Ac an acetyl group: CH3 - C - Cy a cyclohexyl group: 0- o Ts tosyl, or p-toluenesulfonyl group: CH3 � "==1 II S- o o II Boc a t-butoxycarbonyl group (amino acid and peptide chemistry): (CH3)3C -0 - C - Z, or Cbz a carbobenzoxy (benzyloxycarbonyl) group (amino acid and peptide chemistry): 0 REAGENTS AND SOLVENTS DCC dicyclohexylcarbodiimide o-N= C= N-Q DMSO dimethylsulfoxide o II S H3C ....... 'CH3 ether diethyl ether, CH3CH20CH2CH3 Cl 0 MCPBA meta-chloroperoxyhenzo;c ac;d g - 0 -OH MVK NBS o methyl vinyl ketone g H3C ....... � N -bromosucci nimide O�O N I Br continued on next page viii < )-CH2-0 - g-
Symbols and Abbreviations,continued REAGENTS AND SOLVENTS,continued PCC pyridinium chlorochromate,CrO3·HC·N CH3H HH CH3 SiaBH disiamylborane H- -S-B-C- C-H CH3 CH3 CH3 CH3 THF tetrahydrofuran SPECTROSCOPY R infrared spectroscopy NMR nuclear magnetic resonance spectroscopy MS mass spectrometry UV ultraviolet spectroscopy parts per million,a unit used in NMR hertz,cycles per second.a unit of frequency MHz megahertz,millions of cycles per second TMS tetramethylsilane,(CH)4Si,the reference compound in NMR s.d.t.q singlet,doublet,triplet.quartet.referring to the number of peaks an NMR absorption gives nm anometers.10meters(usually used as a unit of wavelength m/z mass-to-charge ratio,in mass spectrometry 6 in NMR,chemical shift value,measured in ppm 入 wavelength frequency OTHER a,ax axial (in chair forms of cyclohexane) e,eg equatorial (in chair forms of cyclohexane) HOMO highest occupied molecular orbital LUMO lowest unoccupied molecular orbital NR no reaction o.m.p ortho,meta,para (positions on an aromatic ring) A when written over an arrow:"heat";when written before a letter:"change in" 8,6 partial positive charge,partial negative charge energy from electromagnetic radiation(light) [alp specific rotation at the D line of sodium(589 nm)
Symbols and Abbreviations, continued REAGENTS AND SOLVENTS, continued PCC pyridinium chlorochromate, Cr03· HCI • N� ') CH3 H H H CH3 I I I I I Sia2BH disiamylborane H - C-C-B-C-C-H I I I I CH3 CH3 CH3 CH3 THF tetrahydrofuran o SPECTROSCOPY IR NMR MS UV ppm Hz MHz TMS s, d, t, q nm mJz 8 A v OTHER a, ax e, eq HOMO LUMO NR 0, m,p infrared spectroscopy nuclear magnetic resonance spectroscopy mass spectrometry ultraviolet spectroscopy parts per million, a unit used in NMR hertz, cycles per second, a unit of frequency megahertz, millions of cycles per second tetramethylsilane, (CH3)4Si, the reference compound in NMR singlet, doublet, triplet, quartet, referring to the number of peaks an NMR absorption gives nanometers, 10-9 meters (usually used as a unit of wavelength) mass-to-charge ratio, in mass spectrometry in NMR, chemical shift value, measured in ppm wavelength frequency axial (in chair forms of cyclohexane) equatorial (in chair forms of cyclohexane) highest occupied molecular orbital lowest unoccupied molecular orbital no reaction artha, meta, para (positions on an aromatic ring) when written over an arrow: "heat"; when written before a letter: "change in" partial positive charge, partial negative charge energy from electromagnetic radiation (light) specific rotation at the D line of sodium (589 nm) ix
CHAPTER 1-INTRODUCTION AND REVIEW 1-1Na1s22s22p3s P 1s22s22p63s23px3p3pz Mg 1s22s22p63s2 Al 1s22s22p63s23px1 Cl Is22s22p63s23p,23p,23p2 Si 1s22s22p3s23p3p Ar1s22s22p3s23p,23p,23p2 HHH (a)H-N-H (b)H-6-H ⊙H-0-H@H- -H HH HH eH-C---HmH-C--C-HH-C-- HHH H HH H (i)H-B-H 0-B-的 H :O:H H (h)H-C-C-C-H The c HHH vreroorom because it has only three valence electrons. 1-3 (a):N三N: b)H-C三N @)H-9-N=9@)9=c=g eH-C=N-H0H-C-Q-HgH-c=c-年：)H-i=N-H H H 1-4 (a)⑧N三N⊙ 仙-0日8是8 ⊙⊙ on-e-Rn 0 n-8u n-e-g H There are no unshared electron pairs in pars(i).(j).and(k)
1-1 Na Mg AI Si CHAPTER I-INTRODUCTION AND REVIEW 1 s22s22p 6 3s 1 1 s 22s 22p 6 3s2 Is 22s 22p 6 3s 23px 1 1 s22s 22p 6 3s 2 3px 13p y I P S CI Ar 1 s22s 22p 6 3s 2 3px 13p y 13pz 1 1 s22s 22p 6 3s 2 3px 23p y 13pz 1 1 s22s 22p 6 3s 2 3px 23p y 23pz 1 1 s 2 2s22p 6 3s 2 3px 23p y 23pz 2 1-2 In this book, lines between atom symbols represent covalent bonds between those atoms. Nonbonding electrons are indicated with dots. H H H •• + I I I (a) H -N-H I (b) H - O-H (c) H-O-H (d) H-C- C-C-H H H H I I (e) H-C-C- N -H I I I H H H H I H :0: H I I I (h) H-C-C-C-H 1-3 I I I H H H H H I • • I (f) H -C-O-C-H I • • I H H I I I I H H H H H H I I (g) H-C - C - F: I I H H (i) H -B - H I (j) : F-B-F: - - I H : F: .. The compounds in (i) and (j) are unusual in that boron does not have an octet of electrons-normal for boron because it has only three valence electrons. (a) :N N: (b) H - C N: (c) H-O - N=O (d) O==C=O (e) H -C=N- H I H H :0 : II (f) H-C-O-H (g) H -C == C - CI : I I •• H H (h) H -N=N-H H I (i) I H-C==C-C-H (j) H - C==C==C-H (k) H-C C - C-H 1-4 I I I H H H (a) G}J -NQ) 8 (e) H - C=N - H I H (b) (f) H-C NeD C)J(D I I H H (c) 88(.:) H - O-N O 0) 0) • II ·8 H-C-O-H 8 8 (g) H - C == C - CleD I I 8 H H There are no unshared electron pairs in parts (i), (j), and (k). 1 (d) I H 0) 0) o == c=o 0) 0) 88 (h) H-N=N-H
1-5 The symbols"and"indicate bond polarity by showing partial charge.(In the arrow symbolism the arrow should point to the partial negative charge.) 088088 08- 间&§@8-8 0-8g8-8m§-8 0§-含088 1-6 Non-zero formal charges are shown beside the atoms H-N之H: HHH In (b)and (c)the chlorine as chloride ion.There is no covalen bond betwe choeomim he omula H C-H (e)H-C*-H (1)H-C-H (g)Na'H-B-H H H H h)Na*H-B-C三N: H-C-6CH H-O-N-H H H、HH (k)K*-c-c ()H-C=0-H HH H Reeo6N5代6来"零TRONS ARE SHOWN 1-7 Resonance forms in which all aton IN DIFFERENT POSITIONS. :0: :o: :o: a识-c-g:→过-0=9·→总=C-09 0: :o: 过--0。过-8=日一总=9-每 2
1-5 The symbols "8+" and "8-" indicate bond polarity by showing partial charge. (In the arrow symbolism, the arrow should point to the partial negative charge.) � � � � � � (a) C-C1 (b) C - O (c) C-N 1-6 (a) 8+ 8- 8- 8+ (g) N-O (h) N -S Non-zero formal charges are shown beside the atoms. H H 1 1 + .. - H-C-O-H (b) H-N-H : C1: 1 1 + 1 H H H 8- 8+ (i) N-B H 1 H H 1+ 1 (c) H-C-N-C-H 1 1 1 H H H .. - :Cl: In (b) and (c), the chlorine is present as chloride ion. There is no covalent bond between chlorine and other atoms in the formula. H - • • I + H 1- (d) Na+ :O - C - H (e) H-C-H (f) H - C-H 1 (g) Na+ H - B-H (h) Na+ I H H 1 - H-B-C- N: I H H H H ,1/ C H - •• 1 / ·• O- C-C-H • • I ' C H /1' H H H 1 H H H , / H (i) H-C-O-C-H / 1 + H •• _ •• ' H (I) :F-B-F: 1 : F: .. H-C= O- H 1 + H U) I H H 1 H - O-N-H + I H As shown in (d), (g), (h), and (k), alkali metals like sodium and potassium form only ionic bonds, never covalent bonds. 1-7 Resonance forms in which all atoms have full octets are the most significant contributors. In resonance forms, ALL ATOMS KEEP THEIR POSITIONS-ONLY ELECTRONS ARE SHOWN IN DIFFERENT POSITIONS. :0 : " (a) :O- C-O: .. .. :0 : " . . - (b) :O -N-O: .. .. + . . - : 0: - .. 1 :O- C=O . . - :0 : - .. 1 :O- N=O + .. ... 2 .. - : 0: 1 •• - O= C-O: : 0: I •• - O=N - O: +
1-7continued 回：0-N=g→9=N-湖 H-c=c-c-H --H-c-c=c-H HHH HHH (f)Sulfur can have upto 12 electrons around it because it has dorbitals accessible. 0: :0: :o: 0: :0: 0 0： 0 9-=9→==g 0: 0: (g) H H H -C-H H -C-H H-C-H H H H 0 H H H 0 H-C-H H-C-H H-C-H H separation. ()H-C-N=8 →H-N-g:→H-C=N-女：((negative H0: H:O: H:0: atoms)gativ minor minor major 3
1-7 continued .. - (c) :O-N=O .. .. O=N-O: + + (d) H-C=C-C-H .. .. H-C-C=C-H I I I I I I H H H H H H (e) H-C=C-C- H .. .. H-C-C=C-H I I I I I I H H H H H H (f) Sulfur can have up to 12 electrons around it because it has d orbitals accessible . (g) : 0: II :O- S- O: II : 0: H I H-C-H I H :0 : I I H-C- C+ I \ H :0 : I H-C-H I H .. .. - : 0: I .. .. :O -S=O .. .. II : 0: H I :0: - •• II :O- S=O I :0: H I H-C-H I + 0: 1/ H- C-C .. I \ H :0 : I H-C-H I H .. . . - :0 : I O==S-O: .. .. II :0 : . . - :0: I .. .. O==S==O I :0 : H I H-C-H I H :0 : I I .. H-C-C I \\ H + 0: I H- C-H I H / :0 : II •• - O=S-O: I :0 : . . 1-8 Major resonance contributors would have the lowest energy. The most important factors are: maximize full octets; maximize bonds; put negative charge on electronegative atoms; minimize charge separation. • • - + . .- + + (a) H-C-N=O .. .. H-C-N-O: .. .. H-C=N- O: (negative charge on I I I II I I electronegative H :0 : H :0 : H :0 : atoms) mInor minor major 3