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DOOOLES IN THE MEMBRANE ORGRNIC CHENISTIEN INTRODUCTION TO THE FUNDAMENTALS AND PDPERTIES OF ORGANIC CHEMISTEN., HNDEOGEN TRI@ONAL AR, TRAHEDEAL WMMere cats Sianerexca, CHa CH, SH FUNCTIONAL AkOUP: RSH (22)-BROM0-(3k)-FWORDBUTANE = HVDROKIDE 10M ~ OH NUCLEOPHIG. ORGANIC. CHEMISTRY | INTRODUCTION TO THE FUNDAMENTALS OF ORGANIC CHEMISTeY: VOLUME | TABLE OF CONTENTS cont OF THE BOOK FOCUSES ON INTRODUCING ANID FRMILIREIZING: shall SSENTIRL TRENDS AND TOPICS INTRODUCTION TO ORGANIC: CHEMISTRM : TEENDS IUPAC NOMENCLATURE - FUNCTIONAL GROUPS AND MORE INTRODUCTION TO QURNTUM NUMBERS - PROBABILITY DENSITY AND O2BITALS. MOLECULE ORBITAL THEORN ~ MOLECULAR O2BITALS DIAGZAMS , AND BONDING MOLECULAR GEOMETRY - VSEPR AND ORBITAL HYBRIDIZATION NEWMAN PROJECTIONS , CHCLIC STRUCTUZES, AND CHRI2 CONFORMATION, ISOMERS: STEREOISOMEES AND cHIeAUTY INTRODUCTION TO ALKENE PROPERTIES AND BERGTIONS - MARKOVNIKOV EULE AND THRLOGENATION, - OXIDATION AND. REDUCTION TACD-CATALNZED HVDZATION ~ OKYMERCURATION ~ PECMANGANATE ‘ORMATION OF HALOHY DRAINS INDEOBORATION - CATRUITIC. REDUCTION: -O20NOWISIS INTRODUCTION TO ALKYNE PROPERTIES AND PERCTIONS =EUMINATION OF ()2-DIHALDES - HYDEOBORATION. — HYOZOMALOGENATION - OXIDATION — HRLOGENATION - REDUCTION — ACAD“ CATALYZED HYDRATION RADICAL REACTIONS NUCLEOPHILIC SUBSTITUTION AND ELUMINATION = SNI WMOLECL USSTITUTION = NUCLEOPHI! = SNAPSINSUEGHIRE SMerrOnON TLeRINa aeooes = El CUNIMOLECULA EUMINATION) = ZAITSEV'S RULE — E2 CEIMOLECULA ELIMINATION ) - SOWENTS RETROSYNTHESIS PRINTVERSION #3 (2022) ORGANIC CHEMISTRY INTRODUCHON, WHAT LS THE FIELD OF ORGANIC CHEMNTRY? INTRODUCTION! FORTHE MOST PART THE FIELD OF ORGANIC CHEMISTRY REFERS TO THE ENDLESS AND VAMT GHEMUTRY OF CARBON 6MNED MOLECULES. WE ARE GOING TD EXPLORE CARBON GHAI AND THE FUNCIONIAL GROUPS THAT INFLUENCE THEIR REACTUITY wo ESTER WHY THINK ABOUT ORUANIC CHEMITRY Ad THE LANGUAGE OF CHEMUTRY JUITINE WHEN IERRALING A NEW LANGUAGE IT TANES TIME To BUILD THE RHYTHM, $0 DONOT WORRY iF VOW 00 MOT UNDERSTRAD i ont NOUR FIRST TRY. THE " VOCABULARY OF ORGANIC (HEMILTRN COMES FROM THe FUNCTIONAL GROW THAT CHRNGE THE: BEHRULOR OF TNOIEUAIES /CARBON CHAIN THEY ARE BONDED TO. =~ aunines A cg 0H @ gn TRENDS ° TN MY OFINION, FOCUSING ON THE DIFFERENT TREMOS uNu DF FUNCTIONAL GROUPS AND TOW THEN REACT ww AND INTERACT 1S MORE IMPORTANT 10 LEARNING DRGANIC CHEMIITRY THAN PURE MEMORIZATION. R DF REACTANTS, SOWENITS, ANO PRODUCTS. * IF WE WANT TO CONSIDER FUNCTIONAL GROUPS RU THE " VOCABULARN” THEN REACTION TRENOS EXAMPLE: THE MAIN) REACTION. Wi BE THE "SENTENCE SIRUGURE™ THAT BUILDS TREND FOR CARBOAMIIC DERATUES. INTO THIS LANIQUAGE THAT WE ARE GOING 10 JTUDY. MOLECULAR MODELS DIFFERENT JRILES OF REPRESENTING MOLECULES APPROACH E | LEWISSTRUCTURES: REPRESENT VALENCE ELECTRONS, IONE PRIR ELECTRONS, | ANO BON DING ELERONS AY DOTS AND DAJHES 1 WNOENSED STRUCTURES *1ONE PRI. = SINGLE BOND SHOWS AN THE ELEMENTS BUT EUMINATES OUBLE BOND F-F Na THE BONDING LINES PND ELECTRONS. ELETMENTS 5 TRIPE BOND. : ARE WAITTEN NEXT TO EACH OTHER. PARENTHESES WE ULE D TD REPEESENT SIMILAR 3 SMELETAL STRUCTURES GROUPS 1D THE SAME ATOM. ~ PROTRAVING CARBONS IN CARBON CHAINS Cg CH CH CHy, OR CH CCH) CH HNDAOGEME D8 CARBON CHAILS ARE NOT aie mn DRALIN GUT ALLUMED: COLORS Cane aaa COVOR CODING ELEMENTS CAN HELP W REPRESENT CHOW TO REPRESENT SPATIAL CRAEMEARON) MOLECULES IN DIFFERENT WANS, ‘ON THE PLANE LTHINK: FIAT ON THE PAPER) WME WEDGE - PROVECTING IN FRONT OF THE °o ee ®@ aaNet ro MITE DASHES: PROJECTING AWAY FROM THE PLANE HYDROGEN © CARBON §—OXNGEN = NUTROWEN) CawAY FROM You " " e e 5 ® FLUORINE CHUORINE BROMINE = LODINE aunt Ot n~ n 4 A BALL AND STICK MODEL-THINH ABOUT BALLAND sTICh MODELS FO LEWIS STRUCTURES CW ITHOUT LONE PAIRS) AND WING COLOR (CODED SPHERES AS ATOMS, O-@58-O a-cec-H ex AUNWNE CHCH © SPACE FILING MODEL: 30 MOLECULAR. REPRESENTATION, Tiny FocusEsON THe PROPORTION LeNSTEED OF ADM IN THE LEUMIE. IN THLE MODEL/ REPRELENFATON THE Aron. ARE BUNDED DIRECTLY With OVERCAPPIKLG CLECERONT Te IDE 1S BRJED OFF THE CLECIRON coud. aK SMELETAL STRUCTURE (g(CH,)2 COCs (ONDENIED STRUCURE (SPACE FIWING MODEL DOODIES-IN-THE- MEMBRANE TUPAC NOMENCIATURE UNDERSTANDING IUPAC NOMENICLATURE AND How TO WE IT HAVING CIAL uo CIRNOAKOILED NOMENCLATURE RULES Fo AFFIXE GLUES a\tows Wo maT THE NE Wit THe tact nee RAD. PUNCHONAL GROUP PLACEMENT IN THE MOLECULE POETIC" THE DegiNMiNtG STEM 9F THE WORD rE: THLAL THE Wat S Niifocen 8 fordten QUEFIK: RODED ATTINE END FTE WORD, © SUEUR © CHLORINE: METHANGI (Hg OH oH METH ETHANOATE Aor METHY! AMINE CHgNA, NH, ETHANDIC AUD Daou ETHANOYI LHIOMIDE METHANETHION CHgsH Dra : ) a @doovies-inm-THE-MEMBRANE TUPAC NOMENCIATURE UNDERSTANDING IUPAC NOMENICLATURE AND How TO WE IT Waal ATAICT ANO STANDARDIZED NOMENCLATURE RULES FOR AFFIXE AMUNG MOLECULES ALOU WTO MTU THE NAME UATH THE. EXACT HAPE RAND FUNCTIONAL GROUP PLACEMENT IN THE MO PREFIX: THE DOOINMMING {TEM OF THE WORD ONE OF THE MosT IMPORTANT TMere: BULL WiTHAd THE WORD APFDC RULES IN, TUPAC NOMENCLATURE. SUEFIX: RODED AT TNE ENO OFTHE WORD Rafer nie Numacg or cnkbon NU MBER, PRAIES SANG otanic chemistey 16 THE ctu0N OF HUDROCAREONS, THIS RULE CAN BE AID TO BE THE MOST IMPORTANT SINCE IT IMPUES THE MOLECULE’S LENGTH. ARENT (HAIN LONGEST CRREON CHAIN IN THE MOLEWILE BRANCHES (MALLER CARSON CHAINS OFF THE PARENT CHAIN, WUMPERING PREFIKES: NON- (MCC HYDROCARBON CHAINS SHOWCAJE THE PRITERN: Co Hane, HYDROCARBON SUFFIXES. 1 RUMANE Chu SINGLE BONS” SATARRIEO) "ANE 72. BURENE CONTAINING A DOUBLE BONO- UNSATURATED) ~ ENE 3. ALAYNE CONTAINING A TRIOLE BOND ~ UNSATURATED) ~ YNE CARBON BRANCH INFIX RULE: RULES IMPLYING CARBON CHAINS OFF THE PARENT CHAIN: ~ yl. \ 2 3 4 5 © 10 ~ BUTRNE PENTANE. 1- METHYLBUTANE @doovies-inm-THE-MEMBRANE PARENT CHAIN LEARNING a. te IDENTIFY THE LONGEST CONTIN WOUS CHAIN, JUEST PARENT CHAINS ABE NUMBERED / METHANE (> METHOXY ETHANE METHANOL WPACNOMENICLATURE: CARGON CHAIN, BRANCHING, ADENTIFYING PARENT CHAINS IN HVDROCARBONS. CARBON CHAIN BRANCHING NOMENCLATURE: Ct \ ( \ — T-MOHNI- BUTANE. PARENT CHAIN WHEN NAMING HVDROCARBONS WE ROW WE FONOU THETUPRC NOMENCLATURE PREF RULES THE MOLT TMPULTANT SHE THOUGHT (2 10, DENT APIME LONGEST UNER@ CHAIN (PARENT MAM IME. FARSTIN TS 8 Ui ERUVEAC I FOULDLD TRE VIER, © UTE eulANE = =Y™ Sk 2-METHNL- BUTANE NOW FORTHE THIRD EXAMPLE ce Re FNGHT HESIATETO NAME i 2-E1H' Bac Ore He THE we is 1 BEAN Temiemaoer gman 2 NAW IF We Lee ROIWIE THE NOW WESEE HOW THE LEUALE If ERNIE 10 LQ om IDENT A: 3- METHYL- PENTANE S-MEIHYL- PENTANE DOODIES-IN-THE . MEM O@LANE TUPAC NOMENCIATURE UNDERSTANDING IUPAC NOMENICLATURE AND How TO WE IT AFF \ XE Ss WAVING cTRIGE AND CTANORROIZED NOMENCLATURE RULES FOR MING MULECALES ALLOWS WTO MATL THE AME WiIH THE. EXACT NAPE RND FUNCTIONAL GROUP PLACEMENT IN THE MOt PREFIX: THE DEQINNING STEM OF THE WORD AN "RGROUP"IN ORGANIC CHI EMSTEN WMFIK: BUILT WiTHLAL THE WORD REFERS TO THE CARBON JHELETON SUFFIX: RODEO AT THE ENO OF THE WORD. THE MOLECULE EXAMPIE: ALCOHOLS ROH AFUNCTIONAL GROUP IS A SPEC FUNCTIONAI GROUPS Bieied oa IMMLEGALES PA AHAICHANG ES THE ROPERTI 7 SAND iINFUE a REACTIVINN, EXAMPLE, CARBON - CARBON CT NOS ARE EAVILY eS omen IN IEMICRURERCHONS AND ELecTRONCUNTIGE FONCTION : R UAE UEOURETCAN, PUTTELECIEON. DeNuTY AIFING NCIGHODURING CONNECTED CARBONE ImenttiNe PoIbLe RERCTIONS SPECIFIC FUNCTIONAL GROUPS HAVE DIFFERENT AFFIX RULES TO AUOW THE NAME OF THE MOLECULE TOMATCHTHE SPEGFIC STRUCTURE (WPRC EXAMPLES PREFIXES FUMORINE: FLUORO~ CHLORINE F 1 CHLDRO- BROMINE Br BKOMO- R TopomeTHANe gL TODINE Topo- Rarours BUA I~ SUFFIX Rta “AMINE ROH” - OL ONE AL METHYLAMINE GIREONNERCIO —oeRCD RNA, -en- ayn NUMBERING: NUMBERING HELPS WDENTIEN WHICH CARBON THE FUNCTIONAL GROUP BELONGS 10 @doovies-inm-THE-MEMBRANE TUPAC NOMENCIATURE UNDERSTANDING IUPAC NOMENICLATURE AND How TO WE IT Waal ATAICT ANO STANDARDIZED NOMENCLATURE RULES FOR AFFIXE AMUNG MULELALES ALLOWS US TO MATA THE NAME WITH THE EXACT IHAPE RNO FUNCTIONAL GROUP PLACEMENT IN THE MOLECULE. PREFIX: THE DOOINMMING {TEM OF THE WORD eTWANe TMere: BULL WiTHAd THE WORD A SUEFIX: RODED AT TNE ENO OFTHE WORD ( CIASSIFICATION, CURSMIFICATION OF CARBON ORI CARBON CHAIN WE THE SPECIFIC NOTATION 26, 5°,4°) WHICH REFERS TO THE CLALSUFICATION OF CARBONS {5 ON MuMBet OF BONDS N SPEEIHE REFEEENCE CARGON! 15 BOND- FOR CARBONS BONDED 14 GROUPS (se?) 0 TO. METHANE \" PRIMARY CARBON: A CARBON BONDED 10 ONE OTHER CARBON rc CP HYDROGEN If R HVDROGEN BONDED 10 A PRIMARY CARBON) chy 2° SELONDARN CARBON.’ A CARBON BONDED 10 TWO OTHER CARBO! a (20 HNDROGEN 1S A HYOROGEN BONDED To A SECONDARY CARBON: GpgBons WU 3° TERTIARY CARBON: A CARBON BONDED To THREE OTHER FREON ). (3° HYDROGEN IS A HYDROGEN BONDED 70 A TERTIARY 4° QUATERNARY CARBON: A CARBON BONDED TO FOUR OTHER CARBONS CS 2,3- DIMETHNLBUTANE metHy! AY BRANCH 2-METHMI BUTANE @doovies-inm-THE-MEMBRANE TUPAC NOMENCIATURE UNDERSTANDING IUPAC NOMENICLATURE AND How TO WE IT WAVING TAICT ANO (TANOAROIZED NOMENCLATURE RULES FOR AFF (xe S Whenntd MOLE GILES ous Ue TO mata THe wAMe WITH THe EXACT IHAPE RNO FUNCTIONAL GROUP PLACEMENT IN THE MOLECULE. PREFIX: THE DOQINAIING STEM OF THE WORD. / METHANE WWFIK: BUILT WITHLAL THE WORD SUFFIX: RODEO AT THE ENO OF THE WORD. AU SP HNBRIDIZED, ry | 4 Tht WOMENCLAMIRE CAN ALCO GIVE Us some INSIGHTS AeOUT HOW THE CARBONS ARE HV BLIOI ZED. HYBRIDIZATION RELATES TO HO! E ATOMIC ORBITALS ARE ARZANGED TO OPTIMIZE BONDING ORIENTATION WHILE MiMMiZING REPULSION IN THE MOLECULE. naues $03 HYBRIDIZE D TETRAHEDRAL GEOMeTRN 7 NES -SP2 HVBRIDIEED TRIUONALPLANAR GEOMErRN 1 NES - SP HVBRIDIRED LINERR GEOMETRY I-PROPYNE e . cageeH ETHANE. ‘ ig Clg TH CARBONS r THANE ARE HVBRIDIZEO. Bor We sPa SINCE THIS MOLECULE CONTAINS A TRIPLE BOND C=) Wi INE THE PERE wtaaays . ARE SPS HYBRIDIZE. Chg Cit, CH, CH, CH 1° BUTANE na ~ \ sp? FROM THE NAME Wentoizeo we CANTONESE THAT 7 CARBONS CARBONS ZANID 3 ARE SP? HNBRIDIZED WHILE THE REMAINING Cig Cit 2 CH Crs CARBONS ARE SPS HNBRIDIZED. 2- PENTENE a @doovies-inm-THE-MEMBRANE TUPAC NOMENCLATURE EXAMPLES TUPAC NOMENGATURE EXAMPLES - NAMING DIFFERENT MOLECULES z FN, ETovoeurene 4 say? 2- PENTANIMINE @doovies-inm-THE-MEMBRANE TUPAC NOMENCLATURE EXAMPLES TUPAC NOMENUAMIRE EXAMPLES - NAMING DIFFERENT MOLECULES v 2 we COMMON NAME: \SOPROPYL ALCOHOL 2-PROPANOL iS) ' a HEXANE ai) CARBONS NRE AY SPPTNERIDN METHANOL Funcnonat CYCLOHEXANE GROUP OH 2° cube Prete RESENTS CUCUC “STRUCURES o EIHANOL FUNCTIONAL ‘GROUP: oF ~~ Ni, ° : 1° B ° : . P PROPAD ETHANAMINE. fo @doovies-inm-THE-MEMBRANE FUNCTIONAL GROUPS MORE EXAMPLES OF OME FUNCTIONAL GROUPS, Cg Or AUN HALIDE D0ODIES-IN-THE - MEMBRANE PROBABUUITY DENSITY EXPLAINING THE BENEFITS OF REFERRING TD ELECTRON DENSITY XG WAVE PARTICLE DUALITY : THE PRINCIPAL WHERE ELECTRONS HAVE CHARATERICTICS OF BOTH WAUES RAND PARTICLES THIS HELPS US DERIVE A MODEL Te EXPLAIN BND STUDY THE BEHAVIOR OF ELECTRONS IN ATOMS. Louis DE BROUILE: REPRECENTED HOW A WANES WAVELENGTH Is ASSOCIATED WITH ITS ENERGY, AND HENCE,THE ENERGY OF THE PRETICLE WAVELENGTH: GISTANCE (nm) BETWEEN TWO CHARACIERISTICS OF A WAVE ADJACENT CRESTS OR TROUGHS FREQUENCY : THEN Um BER OF WIAUE CYCLES PER UNIT WAVELENGTH DFTIMELASOGATED WiTH THE ENERGY OF THE WAUE), WRUELENGTH AND FREQUENCY ARE INVERSE RELATED. commer WANE HIN A LARGER WAVELENGTH ommmmer WAVE HALA HIGHER FR AND JUST UNE WaUES, WHET CHEMICAL BONDING, WE Will Am PUTUDE FE COMBINATION OF WAUES WITH CON DESTRUCTIVE INTERFERENCE. TROUGH on SCHRODINGER PROPOSED RN EQUATION To HELP ECRRSBINGER. DESCRIBE THE WANE FUNCTION OF ANN SYSTEM * ' GeNeRALcne: AY=EW THE TIME-INDEPENDENT SCHRODINGER EQUATION: ht 20 tvae=en 2M Ox: BUT HERE If THE ISSUE = THE UNCERTAINTY PRINCI PLE STATESTHAT SINCE AN ELECTRON IS ACTING AS A WE, CANOE SIMUCTANEOUSLY MEASURE Bott THI ui JON AND WELOCITY | = NODE WHEN W2= 0 Z Mis is wit we Foes on eeoonpinty ND PROBABIL OF FINDING DENSITIES BY SQUARING THE WAUE FUNCTION, THE ELECTRON, WE CAN PLOT AO MODEL oF THE PROBABIGIY OF FINDING AN ELECTRONLIN SPACE. WE Will THEN HAVE REGIONS OF HIGHER AND LOWER PROBABILITY, THIS Will INFLUENCE THE GEOMETRIC SHAPES OF ATOMIC ORBITALS Q@ooopies. in-THE-memeRANE ATOIUG ORBITALS QUANTUM Num BERS AMD FONG ORBITALS INTHE PREVIOUS INFOGRAPHIC WE LEARNEO THAT THROUGH JQUARING THE WAVE FUNCTION (Y*) WE CAN FINDTHE PROBRBIIITY DENSITY OF FINDING THE ELEGRON ALONG THE WAVE ATOMIC ORBITALS ARE 3D GEOMETRIC. Quantum NUMBER REPREFENTATIONS ENLOMPALLING G00 OF THE ELECTRON PROBABILITY DENSITY THE QUANTUM NUMBER! E:RBLSH CHARALIERITICS OF THE ARRPHICAL PION RELATING 10 THE WAVE FUNCTION. PRINCIPAL QUANTUM NUMBER: DESCRIBES THE ENERGY ASSOCIATED WITH THE ORBITAL (n) ANGULARQUANTUM NUMBER: DESCRIBES THE SHAPE OF THE ATOMIC ORBITAL FOR AGIVENN VAWETHERE ARELI-1 POSSBIUTIES OF ORBITAL SHAPES FOE THAT ENERGY LEVEL LE) MAGNETIC QUANTUM MUNEE | BESCELBES THE, SPATIAL DLLENTATION DF THE ORBITAL POSSIBLE VALUES £> 2 INCUWDING ZERO (mL) 4+ ORBITALS WITHIN THE SAME N VRE ARE JAID'TO BE INTHE GAME PRIRGPAL LEVEL CSHEID * ORBITALS WITHIN THE SAME NAND £ VAWLES ARE SAID 10 REIN THE SAME JUB LEVEL C SHELL) ORBITALS (2=0) gone, L@=2) i fi a a UWORRESPONDS 10 A CLOVER SHAPE = 0.CORRESPONDING TD A SPHERICAL SHAPE, 53 NODES = 2 OR Noves= 0 me-0 . Q vom NODES=2 Ns3 NODES=Z a2 caspian (eei) FV CORRESPONDING To A DUMBI be Mert aye SHAP mert2 dry g 2 NODES=1 Q=2 Noves=1 Let % met 2Px FORGITALS (23) 4-3 CORRESPONDS TO COMPLEX SHAPES WITH MORE LOBES THAN D ORBITALS. G8" a3 mers Nopes=3 NODES= 3, N=3 npesez ee 3 Nove=z =2 meen axe Tero a2? NODES = 3 DOODIES-IN-THE . MEM ORANE PROPERTIES OF ORRITHLS Nod ESS Mmeinceense inencnaycreincrat QUANTUM # (Nd) THE SIZE OF THE ATOMIC ORBITALS WININCRERSE — uM THE PROBABILITY DENSITY FURTHER FROM THE NUCLEUS. Augmer eoees AVE TO REALIZE 1S THAT AS WE INCREAJE IN ENERGY, WE WIIL INCREASE IN THE FOR EXAMPLE: THE IS ORBITAL TAS ZERO NODES BUT THE 2s ORBITALHAS | AND THE 3S HAS 2 THE PROBABILITY VS. RADIAL COMPONENT GRAPH SHOWS SPHERICAL NODES. NOW THE ORBITALS INCREASE IN BOTH

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