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Organic Organic Chemistry v I 7 iAtom39s and Molecules Atomic Structure Nucleus protons neutrons Volume around nucleus occupied by orbiting electrons a mu mm mm Eduuiicn Obtaining the Noble Gas Configuration 9 Most chemistry is 15 dominated by the drive to obtain a noble gas configuration stable electron configurations 5 Atoms and Atomic Orbitals TABLE 11 Some Ionization H 1360 075 1 Fl B C 830 1126 024 127 Al Si 599 815 046 124 O F 1453 1362 1742 0 147 3134 P S 104 1036 1297 177 2118 361 Pauli Exclusion Principle No two electrons can have the same values for all four quantum numbers 132 has two electrons in the 1s orbital and each is distinct The Aufbau Principle The Aufbau principle states that orbitals are filled in order of increasing energy The greatest number of unpaired parallel spins has the lowest energy Hund s Rule Atomic Orbitals porbitals Relationships between the Quantum Numbers TABLE 14 Relationship between n l and m n l m Orbital Designation 1 0 O 1139 2 0 0 25 2 1 1 2 2 1 0 2p 2 1 1 2 3 0 0 35 3 1 1 3 3 1 0 3p 3 1 1 3 3 2 2 3d 3 2 1 321 3 2 0 3d 3 2 1 32139 3 2 2 321 Lewis Structure Example for Ethane SC Four valence electrons each 1H One electron each kl H H H I H H l H lt H gt Hzg 9H HicgciH H H l H H H H Ethane All valence electrons are incorporated into 0 0 and 0 H bonds Ionic Bonds Ionic bonds as in NaF Kl etc form when one atom transfers electrons to another Ions are held together by electrostatic attraction c Na c1 Na t Na 591 Naf j1z sodium chloride Covalent Bonds and Lewis Structures Covalent bonds are made by the sharing of a pair of electrons between two atoms an idea set forth by G N Lewis AA gtAAA A A2 Two Shared electron separate pair in the A2 atoms molecule Polar Covalent Bonds An unequal sharing of electrons between two atoms leads to a polar bond The more electronegative atom holds bonding electrons closer leads to a dipole moment Two identical atoms share the electrons in a covalent bond A A equally examples are H H and F F Two different atoms cannot share the electrons in a covalent A B bond equally One atom will attract the electrons more 5 b Here B attracts the electrons more strongly than A The direction of the dipole is shown with a plus sign at the AB positive end of the arrow with the symbols 5 and 5 added to show the partial charges Electronegativity the tendency of an atom to attract electrons TABLE 1 5 The Electronegativities 0 Selected ElementsE IA quotA IE J quotB quotIA IVA VA VIA VIIAI 3 B L 1 0 F I 20 5 30 35 40 a A l Si P s C E 15 18 21 25 30 5 Br 118 E 39 E E incleasing Electronegativin 2 5 r h almlmncgauviues um hnra an 1mm um scalp mm by Linux Pauhng Polar Covalent Bonds Dipole Moments 0 c H H HHI H 0i x Hm Water Methanol Ammonia p 185 D u 170 D 1 147 D Resonance Structures ic 5mm ISchlnnrMM i gs Ezdmr Resonance arrow dz 5 WWW mm 1 muggy 3 mm ames Mm r MMMM 39 39 39 395 2 viamu a mam mamas O c O m nu amquot mem acW H H30 Nlt o 2g mankuns C mu mm 04 e nmbwm m i ngatlvn shame 7mm 7 PasI vanhurgu mamas w 17 WEE 3n Nitromethane quotz 2 I mums A Shared Madmm 2 Macaw mm w Resonance Structure Formalism eff 239 HcCQif H30 0 H H NH MH 01 H L r P H9 0 HQN NHz HZN Hz HZN NH H Rules for Resonance forms ndividua resonance forms are imaginary the real structure is a hybrid Resonance forms differ only in the placement of their 11 or nonbonding electrons Different resonance forms ofa substance don t have to be equivalent Resonance forms must be valid Lewis structures the octet rule applies The resonance hybrid is more stable than any individual resonance form would be Molecular Orbital Theory A molecular orbital MO where electrons are most likely to be found speci c energy and general shape in a molecule Additive combination bonding MO is lower in energy Subtractive combination antibonding MO is higher gy Num 3 7 5 An handing Mo 1 unfilled Cumb39wu 39lwn isorhnzls i Banding MD ll lllndl 17 Hydrogen H2 Molecular Orbitals H39ydrogens too close Energy of mm 153 two separated 2 A H atoms Much too far apart Energy bx wquot W Ci f Lquot3 074 A 1 A Optimum Too far apart distance in the hydrogen H2 WOIECU39G gt molecule 0 050 100 150 200 250 300 Distance between two hydrogens A Orbital Interaction Diagram 0 Ha 153 me 18 03 n W 39s W39le m I 1 wEWan 151 MPH15 Orbita nteraction diagram Tahln 53 Sonic Band Dissncinlion Energies u a n D sum kJIllInll am kJIlnnll Emu kJnml HiH m 04330 1 209 C7HFCH3 355 ka 57o H2CCH7H 444 CHCH CH 351 HACK 432 H10CHCI 368 CHC CH 339 H Br w H1CCHCHz H 351 H2CCH7CH5 405 H71 2015 Hzczcucurcx 2x9 Hzccucu H 310 mic 243 H H ltHz m Br Er 192 Q 454 Aka I I 15 I 417 CHrH 438 c CH3 Cl 351 405 cH2 cuJ CHg Er 293 V f U 331 V cHrl m I CHrH CHrOH 380 368 g 368 CHg NH 335 CHaIFH 3 mm mm quotmm mulm Ol39ganlc Chemlsu39y m e Reaction Aciith a 7 Base H A 8 1Aquot H B Acid Base Conjugate Coniugate base acid 7 39 Hp39l I HNH H Q HNH H H Acid Base Conjugate Coniugate base acid Acids and Bases Bronsted acid is a proton donor proton a hydrogen without an electron Bronsted base is a proton acceptor An atom or molecule that is an electron pair donor is a Lewis base An atom or molecule that is an electron pair acceptor is a Lewis acid Electrophiles are Lewis acids Nucleophiles are Lewis bases Ka the Acidity Constant HA H20 2 A H30 H3O PF Ka KeqHZO W IpKa quotlog Ka lThe pKa of water is 1574 0 r8 3 n i C C h e Y Eit 3 CHAPTER 3 Alkenes and Alkynes Alkanes and Alkenes Alkanes have the formula CnH2n2 Cycloalkanes with one ring have a different formula Cann A second family of hydrocarbons also has the formula Cann These are known as alkenes Alkynes are a third family of hydrocarbons having the formula CnH2n2 Alkenes and alkynes are unsaturated they contain fewer hydrogen atoms than alkanes Physical Properties of Alkenes TA BLE 52 Snnw imperJkAum Name Formula mpquotC hp C Emma lhylcnc HCCH3 169 103 7 Pmpcne pmnv39mnr 1H cnicn 4km IT 4 I Emmv H3CCHIH CH 35 b 3 Burcnc CH CH CH CH 1199 7 rrrmr Huh Hr CHaic iC iCT h i109 09 2Mcthy1mopcnc isobuRM CH zCHiCJi 407 is 1 Pm39lrl39ne 39 7 39Halr57CH 4155 01 lIchcnc 112C7C117CIIL17CI13 1393 133 1 ngmno H I 1 39HW 7 3 7119 03 h lOctcm Illcicllv CI 7C1 41017 213 lIVOncnc H LCH7CH3L7C 1 83 146 1 Dt39n39m H 7CHCH77CH Arm 17M Alkenes H H C C H H Ethylene IS Carmene orange pigment and vitamin A precursor ram kmnn my mun Uses of Alkenes CHJCHZGH Hocuzcnzou CIcHICMECI Emmi Ethylene glycal Ethylene dkhlovlrlo 0 o o n H II I c c crich 01ng Hzcickz H H Awaklehyde Acetic cid Ethylnu oxid Emvlmu manI H2CCHOCCH3 CH1CH2n HgCCHK21 Vinyl Iceuln Pawmm nyl mlmda DH 0 CH3 1 CH3CHCH3 HzcichHq chachj hnpmpyl Fmpylenz Polypropylene H 1W alcohol oxld C C H II H cu J Fropviene CM propane Cumen sz Orbitals and the Pi p Bond 2px 2p 21 Hmquot V HM NH H quotaclt o i c39 gt 39c 39 c c 3703 33 quot 0 0 quot sp2 SpaSpec Bond sp2sp2 a Bond Hl Illllll H H y T w x V a quot0 1 c C H H QC H The coded represemation for a double bond note at there is no distinction made between the ci and y b a typical CC bond distance is 133 A Nomenclature of Alkenes IUPAC names of alkenes are based on the corresponding alkane with ane replaced by Ilene HZCZCHZ CH3CHZCH2 Q systematic name ethene propene cyclopentene common name ethylene propylene Nomenclature Examples y K vquot r7 7v 3 ens 13Bumuiene A ND 3amen9 V aMelhyl1 Ahemadiene a Promlinonene naryw zmxgna rm Avlnyldanlne L K T J V I a 1Melhylcyclahexene SMethylcyclahexene ZMethylLacyclohexadlene ncr enmnwcynlqhexsne noxsdnemymg cygohexadlgni 5 Cis and trans isomers cisMuhna mamwuumu mm Emulw w trans ZBumne Low High priority H i C priority C C g High CH3 5 CH3 Low priority priority 3 EiZChloroZbutene c 1qu Human mm mum The E 2 System of Nomenclature Low Low priority H i CH3 priority C iC i High CH3 i C39 High priority I priority b ZlZChloroZbutene Alkene Stability Heats of Formation AH AHOf of a compound the enthalpy of formation of one mole of a compound from its elements in their standard states C graphite H2 150nm AH hillmo 111 cncn ugcnlcm rm 0 Lmsrsmbi u on oncucr1lcuA 7112 ms C o H CIICILCII 712 Chi Chuman 16 o CH31CCCH12 n r Nimrsrabi Anegaiive H n rm 9 A Apositive H its formation i5 endothermic requiring energy to be apphed Bicyclic Systems Fused bicyclic system Bridgehead position H H Bridgehead position 0Two shared adjacent carbons Bridged bicycic system Bridqehead pmn H E H H B ridgehead position OThree shared carbons amp Thls double bond Is at the bridge head poslion Bredt s Rule A bridged bicyclic compound cannot have a double bond at a bridgehead position unless one ofthe rings contains at least eight carbon atoms The bridgehead position is the point at which the bridges meet Alkynes Steam 2 CH4 W 3 H2 Methane Acetylene 2004 Thomson 7 Brooks Cole H CEO CEC CEC CEC CEC CEC CEC H A polyyne detected in interstellar space Alkynes V p orbital W a 4 p orbital r np orbital Sp whims K n bond 7 band Cubancarbon triple bond ms pm 113 H C 2 r ec 120 pm mmwmm Alkzncs f TABLE 34 Heals anu n s Hume Relative Heats of Formation for Alkynes rmalion for Some Small Hydrncm39lmn u c AH hullmu 125 48 70 719 us 729 ms Allyn AH hmmu Alkynes H s s a CHrCECiC 2 A u 2 3 4 1 3 2 w HcEc CHz CH3 G CHz 9 c 13 3 2 s a l H CH3 1Butyne tmnsZHexendyne BZhexen4 33Dimethyl1butyne netsbmyns L 1 y 7A CH 0 CHi CECH Elhynylcyclohexane 3Pronynylcyclopentane or cyclohexylacetylene 0r propargylcydopentane Alkyne Acidity Alkanesalkenes have high pKa gt40 values Terminal alkynes differ they are relatively strong proton donors An acetylide anion is produced by alkyne deprotonation Alkynes are more acidic due to higher 5 character 50 5 Greater 5 character lower energy of electron more stable anion Alkene Addition Reactions THE GENERAL CASE A SPECIFIC EXAMPLE HQC CH3 H X H30 CH3 H Br H X H Bl c gt Hacac c CHa c gt Hc c c CHa Hc CHa H30 CHJ HJC CH HJC CH3 H l II c CH 1 7quot H a a H a cc 707mg H s cicioHa H 0 I H36 OH I Proxonauon s CH Aaamon or or 0 CH3 Reaction Energy Diagram Reac cn progress H l or HQ CHsi l i clt lt CH3 H H30 H cc Regiochemistry of Addition H Tl H3C7077H CH3 H This product is not formed Zl H HSC J CHZ CH3 The product of the reaction Order of Carbocation Stability More substituted carbocation is preferred upon alkene protonation CH3 More H More CH3 More H I stable I stable l stable Le than than than H30 CH3 H30 CH3 H H H H Tertiary Secondary Primary Methyl regeneraled have Hydration Mechanism used up here HJC CH H30 CH3 CZC quotAx I H29 9C C H HJC CH3 1 Protonation of H30 CH3 me am Cavbocalion imermediale 2 Addition a H30 CH3 H30 CH I H QH2 HQ C C H Hz C C H HJC H3 3 tgemottonalion HJJ CH3 Alcohol y wa 939 Oxonium ion Cakalyst 5 intermediate Families of Organic Compounds Functional Groups Alkane c c Nitro 39 Io I 0 O Alkene 30 I H Aldehyde CCH Alkyne CEC I o I I I Ketone I C I Alcohol COH II I 39 9 Ether COC Acld ICOH I Fquot I 9 I Amine IIl H Ester CCOC H O Q c 39 v cgziigw O rga n I c C h e m 51 ry W 5 h mu chveu A Fleming H ll39HHDN c HAPTE R 2 Alkanes V NOR39l nN 1r mm mum Hybrid Orbitals and Methane CH4 The simplest alkane is methane C atom is sp3 hybridized 39 4 C SP3 Atetrahedron orbitals overlap with 7 gt 4 H 15 orbitals to form a L 4 sigma 6 bonds All angles are 1095 Methane a tetrahedral molecule b l 109 A l C H 7695 sp hybrid orbitals SD 7 5 The amtcn l g m orbiial CO 3 sn Hybnd f AM g mums symmaw w O Roxa nnaroum H15 mastanus 39 V mumg I Axis H 14 5 15 mahondhg u arblw Example of Heterolytic Bond Cleavage for a Carbocation and a Carbanion a Carbocation formahon b Carbanion formation Hr H Ho 1 Hng 4 Hp H HQH 4 He m H H H H H n n F I HltJ3 H a H ID39 H HiciH 439 Hie H I L H H H The methyl Hydnde The melhy Apmmn cakion Wm Bum mm mm a The Methyl Radical CH4 can undergo homolytic bond cleavage The C and the H atoms each take a single electron from the 0 H bond thus becoming radicals H H H cn DH gt H II H H l The methyl A hydrogen radical atom Arrows with half arrowheads called fishhook arrows imply movement of one electron Potential energy Newman projectionsconformations of ethane eclipsed canformalians HH 2 9 ktaimol oi 12 Kllmul H energy barrier H H 11 i 1 11 11 11 11 H H H H H H H staggered conformations i V i i i 120 24039 i 180 am Degrees of rotation Copyright 2007 Pearson Prentice Hail int Various Conformations of Butane Alkane Nomenclature Common names for first 4 alkanes IUPAC utilizes the Greek prefixes TABLE 24 Some StraightClminAlkancs a e Formu mp CC 171 C Mam CH4 71 71M Ethan cHicH 71833 788 5 Pmme HZC 7129 7 743 1 Emma CHKCHZLCHi 713s 4 70 s Pantanc 3ng CH3 7129 7 35 1 exam LHKCHDoCHi b9 Hepnne CHZiCHJ 7905 95 4 On In qua H 7568 125 7 Nonanc CII C112CIL 751 150 8 Doom CHan 1 719 7 174 1 Undecme CH1CHZ7CHq 725 a 195 9 i d CHACHD quotChi r9 6 216 3 Emoane CH3CH2V 3 36 s 343 o Triammanc CHKCHDmCHi 66 4497 Pcmacon inc CH3CHZ ECH3 92 Constitutional Dilferenl carbon skelelnns H Different lunmlonal gmups cluso Di erenl pasilinn nf funninnal gmupa 1ng W CHgCHCHg ZMathvlpmpanu lsobutane c gt430on Ethanal W CH3CH 5 H3 Isnpmpylumlne Isomers and CHacHZCHZCHg Butane and CH30CH3 Dimelhyl mm and CH3CH2CH2NH Propylnmine Table 32 Numhm Bl Alkall J Isnmers Numhar M isumcrs M47 366310 4 T 1305763 IUPAC Hydrocarbon Naming Nomenclature Rules Find the longest continuous carbon chain Number the carbons starting closest to the first branch Name the groups attached to the chain using the carbon number on the main chain as the locator Substituents appear alphabetically in the name Use di tri etc for multiples of same substituent Nomenclature of cycloalkanes Use the prefix cyclo C 2 Hzc VCH CH HEC CHZ H2C CHI 39 1 H2C CH2 HZC CHZ HZC CHZ Hzc CH2 CH2 cyclopropane cyclobutane cyclopentane cyclohexane Physical Properties of Alkanes and Cycloalkanes Intermolecular van der Waals forces stabilize the liquid phases of hydrocarbons As electrons approach the molecules electron clouds polarize g n inducing dipoles Orgnnlt cnemlsuy 39 duced dipoleinduced Dipole Interactions CH CHgCHZCHZCHICHJ CH3CHCH2CH3 CHJCCH pentane I hp 36 1 39c CH1 CH1 isopemane neopemane bpl7 9 C bp95 39 Nuclear Magnetic Resonance Spectroscopy NMR The number of NMR signals is equal to the number of inequivalent sets of nuclei H C etc depending on the atom being analyzed HCH 0H HSC CH3 H30 CHa Methane Ethane Propane One signal One signal Two signals one for the CH2 and another for the two identical CH3 groups O Q c 39 v cgziigw O rga n I c C h e m 51 ry W 5 h mu chveu A Fleming H ll39HHDN CHAPTER 5 Rings V NOR39l nN 1r mm mum Various Conformations of Butane Strain Energy Torsional Strain electrostatic repulsion between electrons in a bond Steric Strain When bulky groups try to occupy the same space Angle Strain or Ring Strain angles that deviate from the ideal sp3 bond angle of 1 0950 Ol39ganlc Chemlsu39y m a of Cylalane Ring Strain 1139 139 7 quot quot 2 x 17 1 939 umlmdmn u 9 a f49 7 ma39 quot120 gt V X Li Cyclompn Cvdobman Cyclopeman cyd hm n a 2am Thurman mum Emum Rings and Strain Angle Strain cont CH2 2 39 CH 2 Wis 30 6A IR 1040 Hzc l CHz Hzcxl CH2 Cyclopropane Cyclopropane internuclear angle is 60 interorbital angle is 104 Quantifying Strain Heats of Combustion NW Octane Can 125 02 2233Tetrama 1yibutane also 03H 125 02 energy difference between these isomeric compaunds Heai of combustion AH 456 sumo 130760 kcalrnol 130760 130304 456 Energy Heat of combustion AHg 130304 kcaImcl 3002 sto Quantifying Strain Heats of Formation TABLE 51 5min Energies forsom Cycloalknnzs 1 2 3 4 s Mumted CalchH If A11 pa CH2 n Strain e Molecul 5min E 5min 1 pa CH2 Molecule Italmob mlmo mlmo mlmo kmlmnl Cytlupmpnul 12 4 7147 274 v 1 Cyrlubuxmm b 3 39H T 196 264 56 Cyclopnnlauc 1 m 17 245 a 1392 Cyrlnhmne 29 s 4 9 29 4 n 1 o Cycloheptmz 233 74 0 734 1 h o o 9 Cyduomne 297 73 7 739 2 95 1 2 Cyclades u 369 3 7 749 o 12 1 1 2 ydududunmu 55 u 74 6 ss 5 J x o 3 Stability of Cycloalkanes The Baeyer Strain Theory 0 0 Strain energy kJmol m 0 287 239 191 143 96 0 8 91011121314 Ring size kcalmol Chair Conformation of Cyclohexane H H h H CH2 H 2 4 H QHZ H H 39 H chair conformer of Newman proiettion of ballandstick model of the the chair conformer chair conformer of cyclohexane Chair Cyclohexane The six axial hydrogens of chair cyclohexane The six equatorial hydrogens of chair cyclohexane Chair Cyclohexane H H The six equatorial hydrogens All 12 C H bonds of chair Up hydrogens in green ne of chair cyclohexa Cyclohexane axial hydrogens down hydrogens in gray are shown in re 39 hydrogens in blue Chair Cyclohexane Ring Flip Up axial becomes up equatorial Down axial becomes down equatorial Monosubstituted Cyclohexanes Consider methylcyclohexane there are two distinct sites for substitution on the ring CH3 H ring flip e W CH 3 m Equatorial methyl Axial methyl Monosubstituted Cyclohexanes 13diaxial interactions Imerfera E h t 39 mgi in 5 a H 5 CH3 H E 1 Monosubstituted Cyclohexanes TABLE 53 Axial Equatorial Energy Differences for Some Alkylcyclohexanes at 25 C A G39 axeq kcaJm 01 Compound Methylcyclohexane Ethylcyclohexane Propylcyclohexane Isopl39opylcydohcxanc ierz Butylcyclohexane 174 179 2121 2161 55 K 195 212 434 860 11916 12Disubstituted Cyclohexane 12 dimethylcyclohexane has cis and trans isomers CH3 H CH3 H CH CH H 3 CH 3 CH2 CH3 3 H CH3 H H H H Methyl groups cis Methyl groups trans hydrogens cis hydrogens trans 12Disubstituted Cyclohexane cont Trans12 dimethyloyolohexane has two possible conformations This axial meihyl becomes equatorial CH3 H H flip CH3 lt H CH3 H CH3 This axial methyl also becomes equatorial 12Disubstituted Cyclohexane cont Concerning stability larger groups produce more steric strain when they occupy axial positions The more stable conformation of cis lisopropyl 2 methylcyclohexane has an equatorial isopropyl group Axial group CHCH32 H C Axial group 3 H ring fle CHCH32 A CH3 39 6393 cis H A H Equatorial group B H Equatorial group Bicyclic Compounds cont Bicyclics sharing two or more carbons are more prevalent than spiro compounds The fusion positions or bridgeheads are highlighted ltgt lt 31 CD C0 Bicyclic Compounds cont Consider cis and transdecalin H CD H H H Decalin Schematic picture of Schematic picture of cisdecalin fransdecalin I Wm Naming Bicyclic Compounds Bicyclic compounds are named by counting the number of carbons in the ring system this gives you a base name Le a bicyclic with eight carbons has a base name octane Number from the bridgehead C 1 along the longest bridge rst then the next longest then the shortest ifthere are three bridges Assign each bridge a number equal to the number of carbons excluding bridgeheads put those numbers in brackets in ascending order separated by periods between a bicyclo suf x and the base name Naming Bicyclic Compounds cont Numbering examples 5 v 0H LIHz i 3 CH3 7 2 CH3 I 1 Bridge counting naming example 1 Atomlr bridge j 3Atom bridge lt CH 2 Atom I 3 bridge CHa 33Dimethylbicyclo321octane Organic Chemistry 2201 TuesdayThursday 1100 to 1220 PM Office hours TuTh 12301 30 By appointment Franklin A Davis Room 450 Beury Hall 2152040477 Email fdavistempleedu Organic Chemistry 2201 Text Book Organic Chemistry and Study Guide Jones amp Fleming 4e W VllladN wn Study Guide Molecular Models Recommended SmartWork access ebook organic animations QuickTImeT39V39 and a TIFF Uncompressed decompressor are needed to see this picture QuickTime M and a TIFF Uncompressed decqmz ssss or are needed to see this pic ure Blackboard Organic 2201Davis Fall 2012 Content InformationDocuments SyHabus 2201 ntroductionBBppt Grading Review Exam Midterm Exam 1 Midterm Exam 2 Midterm Exam 3 Final Quizzes Homework Total Points 50 200 200 200 200 100 i 1000 Quick39l39imeTM anda TIFF Uncompressed decompressor are needed to see this picture 2201 Instructors for Fall 2011 in alphabetical order Instructor s name BE Office Frank Davis 450 David Dalton 342 Steve Fleming 442 Dave Hill 4268 Chris Schafmeister 340 Email address Lecture fdavistempleedu 1100am TTh daltontem9leedu 100 MWF steveflemingtempleedu 1000am MWF hilltempleedu 530pm T meistertempleedu1 11 00 MWF Course Schedule This schedule is tentative and subject to change Please be a HELP Make certain you take full advantage of all the academic support services available at Temple on the Main Campus and at Ambler These include instructor of ce hours the Math and Science Resource Center MSRC 1810 Liacouras Walk 2quotquot oor Main Campus in addition to Supplemental Instruction sessions The services provided at the MSRC include oneonone tutoring computer lab weekly group tutorialslsupplementary instruction nal exam review sessions and a resource library The center is open 6 days a week AND IS FREE For additional information check hugftwwtemgleedufmsrcl39 DnLine Help I Practice Quizzes h zl lwwwchemhelgercomr39gracticetestshtnl I Organic reactions Quizzes and Summaries httpz pagestowsonedufladonlorgrxsi39reactsumhtm I Organic Chemistry Toolkit httplmwrstolafeduldeptsr chemistmooursesltoolkitsl247i I Organic Chemistry Practice Problems at Michigan State University Excellent httpzllwwwcemmsuedulreuschNirtualTextl39Ouestionsioroblemshtm I Electronic Flashcard httpllwwwchemistmohio stateeduiorganiclflashcardsl SmartWork Online homework Course Course ID Davis TuTh 11001220 Book Organic Chemistry 4th Edition Instructor Davis Franklin Temple University Email fdavistemloleedu Course ID JONES1808 SmartWork Online homework STUDENT SELFREGISTRATION To create a SmartWork account and selfenroll into the class follow the quotFirst Time User instructions at httpsmartworkwwnortoncom Help See Paul Finn His office hours will be announced His email is paulfinntempleedu You will need 1 a valid email address 2 The enrollment key for your course JONES1808 3 a registration code from WW Norton 9 1FDP P 9 NT Organic Chemistry 2201 What is necessary to Succeed in Organic Chemistry You must learn the material You have to memorize things like nomenclature It is important to regularly attend lecture and recitation Read the chapter before coming to lecture Do the problems Review every day Use the summaries at the end of the chapter Stay on top of the material from day one 9 Work in groups 10 Outline the the chapter 11Do lots of writing of the material 12Ask questions 13 Take good notes 14 Use the internet Google 15 Make note cards CH4 SP3 thlvbOndamgleyOfIOQSO WWlfSiWWVWOt WQ amd 39739 3 Cquot 39H H H Ba HF e e BF3 HF gt 813416 f e f a 315 76 gt FBF H F F Use the Resources available See the lecturer See the recitation Instructor Use a Tutor Use the study Guide Use the MSRC math science resource center Wikipedia YouTube Office Hours nance After class 1230 to 130 PM amp by appointment Office Beury Hall Room 450 Suggestions on How to Pass Organic Chemistry by Students 1 Recognize that organic chemistry is not as terrible as the rumors suggest but it is labor intensive 2 Read the textbook 3 Study a little at a time everyday you can t cram everything before a test 4 Go to class and recitations 5 Work extra problems Build models Recopy your lecture notes you may realize there are things you don t completely under stand 6 Model sets are a great resource They re essential to under standing ster eochemistry 7 Working on syntheses ties together everything you have learned 8 If you know the underlying reasons why stuff happens you can gure out a reaction you have never seen before CampEnews April 16 2001 Miscellaneous Be considerate of your fellow students During lectures keep conversations to a minimun Take care of your needs before coming to class Cells phones off or on silent mode Why Study Organic Chemistry Because it is required for my major Because my professional school requires it Organic chemistry provides a foundation for molecular biology and biochemistry Organic chemistry is the study of live and all chemical reactions related to live because it has a role in all life s processes Techniques learned in the study of organic chemistry helps in mastering other information intensive subjects medicine law biology etc What is organic chemistry It is the chemistry of carbon containing compounds Carbon C in combination with other elements including H O N Br F Cl l halogens S P B and certain metals Li Na Mg Cu The study of organic chemistry includes Classification compounds by functional group 00 and nomenclatl Reactions of compounds by type or functional group CC COH e1 Reagents used in reactions Synthesis Mechanisms Stereochemistry Physical properties NQWPWNT 0 r8 3 n i C C h e Y Eit 3 c H A PT E R 4 Stereochemistry Review and Preview We saw that hindered rotation about single bonds leads to different conformational isomers Rotation about double bonds is not possible without bond breakage Other types of isomerism besides conformational isomerism are possible Two molecules may be mirror images of each other and not be the same like a left hand and a right hand This handedness of a molecule is called chirality Molecules having handedness are said to be chiral Kinds of isomers g constitutional isomers I stereoisomers I configurational isomers 5 i dlasteriomers l anantiomers ie lsh ans max CHZXY ITeft hand Right hand Enantiomers These are two nonsuperimposable mirror images Have identical physical properties except for the way they rotate planepolarized light Have different chemical properties with chiral molecules but the same with achiral molecules CH3 CH2 N c H c H CHacH GHQCH I oiichZCH3 CHQCHS 3Melhylhexane 3Melhylpenlane chiral achiral Thalidomide R Thalidomide SThalidomide In the 50 s this drug in racemic form was given during pregnancy to to prevent nausea but was found to produce fetal limb abnormalities Now used in the treatment of leprosy Inhibits replication of the AIDS heals canker sores Being investigated for use in treating tuberculosis Om de are needed kTwmeW and a umpres tn seet sur ms pmture CahnlngoldPrelog Rules Step 1Use the priority system to distinguish atoms on the basis of atomic number The atom of higher atomic number has the higher priority Step 2For isotopes atomic mass is used to break the tie in atomic number Step 3Nonisotopic ties are broken by looking at the groups attached to the tied atoms Step 4Multiple bonds attached to alkenes are treated as multiplied bonds Assign R or S Working in 3D rotate molecule so that lowest priority group is in back Draw an arrow from highest to lowest priority group Clockwise is R Counterclockwise is S is 39mnivmmr m arrowh 3 w 5 cmw errlockwlw c Assign R or S ll3r 13r C gtquotquotI E quotquot C CH3CH2 H H 1 CHZCH3 CH3 CH3 mirror the two isomers of 2bromobutane a pair of enantiomers R S m 0sz m Io39m I m m1 m 0 m 016 m I A 22 A 5 A LnE a 196 m N N m fo39m 0 0 0 I n 330205 wE wEow o mmEmem Physical Properties of Stereoisomers Enantiomeric molecules differ in the direction in which they rotate plane polarized light but their other common physical properties are the same 9H3 i 9H3 CZHsr IH E H39g C2H5 CH2OH CH20H s R a 5156quot 6756 5p 1289 1289 density 06193 03193 Physical Basis of Optical Activity Ordinary light is passed thru a Nicol prism Movable polarizing filterto measure angle The polarimeter measures the angle of rotation of light Unpolarized lig Planerpolarized fr Ia M Dm sodium mp Tuba containing samp e m Chiral molecule i r Emcrgmgiigm H isrolated i l Detector pm I Nicm prism Physical Basis of Optical Activity Prupagmim of Intavadicn oi the light The solution oniains only with n axana so planepolarized light 39 Iii 3meihylhsxane mamamym CH3 1 I 1 CH emerges12 39 Specific Rotation Observed rotation depends on the length ofthe cell and concentration as well as the strength of optical activity temperature and wavelength of light a or observed Col 0 is concentration in gmL is length of path in decimeters Physical Properties of Stereoisomers Table 91 Speci c Rotation of Some Organic Molecules Compound aln Compound aln Penicillin V 233 Cholesterol 31 5 Sucrose 6647 Morphine 132 Camphm 4426 Cocaine 716 chloroform 0 Acetic acid 0 amnmumnxuu my Molecules with More Than Two Chirality Centers The number of possible stereoisomers with n Chirality Centers is 2n Cholesterol eight Chirality centers H GmL JThumsanAamokstale 8 stereocen ters 256 stereoisomers 128 pairs of stereoisomers COCAINE 4 chiral centers 16 stereoisomers 333 w Warm 5 mama enantiomers Threonine isomers co 907 95w gem H NH7 7m H2N H H ampNH I1N H HNH I i HOH MOI HDV EKH Hr HITDH CH5 CH3 CH3 CH O lt i u b x g h V o 39 39 3 man 2535 25135 25317 Enmliomus Emmiumm 9 mu mm mm mama Threonine isomers TABLE 92 39 39 Arno ng ruul 39 of Th reonine Slereoisumer 39 39 2R3 2338 2R3S and 2523 2835 211316 2 3b39 and 283 2HBS 233 2193 and ZS 233 2H3s 2193 and 2533 2004 Thomson Breakslcma Examples of Diastereomers CH HO OH r v zs sz cI c gt 13 H H cHichl I39H H2053 1 Gym c c symmmburzm manunfl H 52H H30 g quotT pug f t I r clgc i c c S2Dhlarobnlne CchH CHrcHg39l 0442041 H RlZclllarnhutan F CH CH r l 31 m cw Cr H H a a 1chn UHan 2Cl Sjvarchlnmbmane II112 an H c CH 3 2 a 4 w RV cricx uiuu szchlombulam quCH H l Var13cm H CHCH2 n wzchlcmhutane Racemic Mixtures and The Resolution of Enantiomers 02H R C H CH3 HO HO HAGCH3 C07H 5 Racemic lactic acid CHENHZ 4 c o H3NCH3 c H CH3 HO H salt M39rmr Enantiomers HO H CH C 3 7 02 H3NCH3 Ssalt Racemic ammonium salt 50 R 50 S Racemic Mixtures and The Resolution of Enantiomers E EOZH W C 3 JH THE H JC H3C HJ39WPhenvltha39mne HO CH 5 H K Z a CDZH Racemic lamic acid 50 R 50 sh om m um mm mm I 02 H35 c c H 1 Ha H39l A H0 H3C l An nasal Dlasmrenmars H bl HD 3 HAJCHa C H coz H3C An an salt Meso Compounds Tartaric acid Mirrnr Mirror 1Q02H QOZH 1DZH IQOEH HieDH HOampH HEOH HO2H HO B 3H HJE OH H a oH HOH ICOQH mozH ACOZH ACOZH 2535 ZRSS 253 2PM qu Symmerrv mama I c Ho 5 com H Chapter 5 35 TABLE 93 ianarlc Add elling 01 Density Solubility at nquot Surmlsnmal polnt 390 degrees glam gm mL up Hi 1687170 12 17593 M 165 170 712 17555 mm Mm 11le 0 16660 1250 chamer 5 31 Comparison of Physical Properties of Diastereomers and Enantiomers Diastereomers have different physical properties mp bp Enantiomers can be separated by resolution Enantiomers differ only in reaction with other chiral molecules and the direction in which polarized light is rotated Diastereomers can be separated by normal chromatography trans12Dichlorocyclopropane Ji CI CH2 H H CH2 Cl c c gtc clt H CI Cl H trans12 Dichloro error cyclopropane Summary of Isomerism Structural isomers have the same molecular formula but differ in their connectivity Stereoisomers have the same connectivity but differ in their arrangement in space Enantiomers are nonsuperimposable mirror image stereoisomers Diastereomers are stereoisomers that are not enantiomers Meso compounds have chiral atoms but overall are achiral due to an internal mirror plane of symmetry 55 Dr Nopper Asian Diaspora Week 8 Articles Writing Assignment Due March 29 Drawing from all of the readings from week 8 Kurashige Crenshaw and the rise of multiethnic Los Angeles and Tsuda When minorities migrate The racialization of the Japanese Brazilians in Brazil and Japan answer the following two questions 1 How were the Japanese internees treated by whites in Crenshaw after WWII and how did this relate to quota global imaginary of integrationquot 1 paragraph The Japanese were the first to experience atomic bombs from the US However the US wanted to reconcile with the Japanese after all they have done to them because they would be their new ally to bring democracy And even the whole story on internment camps were covered up In Crenshaw suburban whites were willingly and openly selling homes to Japanese Americans in ways that were unimaginable before the war Kurashige p 51 The global imaginary of integration was their way of rekindling their connection to the Japanese This is considered imaginary because the main point of this rebuilding was to help with their image propaganda They wanted to once again be thought of as a free and loving country The global imaginary integration is a way to get rid of contradictions that occurred in the past When we did everything other than what they said they were a free country 2 How were Japanese Brazilians treated by Brazilians and how did views of Japan s place in the global economy influence this treatment 1 paragraph In Brazil the Japanese were looked up to it s amazing how many Brazilians want to learn Japanese Tsuda p 236They were put on a pedestal and admired there were plenty of positive images about Japan s industrial development prosperity and advanced technology Tsuda p 233 And the Brazilians would make gestures that we consider offense to them however that was not their intention The Japanese had a good image in the global economy Their products were thought to be better than the Chinese and the Koreans less cheap Basically they were treated in the same way the Chinese were treated in South America They were considered the model minority There was an obvious admiration there was a notable consensus among Brazilians that the japon s are hard working honest intelligent trustworthy and responsible which is partly the result of their notable success as a socially mobile and highly educated immigrant minority Tsuda p236 They were well respected
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