COLLEGE:

Science

DEPARTMENT: Chemistry

COURSE CODE:ORGCHE1/Organic Chemistry 1 for Chemistry Majors Prerequisite: Prerequisite to: o" of units $erm %ca&emic year I OCHE! ORCHEM! # units

CLASS DAYS AND CLASS TIME:__________ ROOM:_____ INSTRUCTOR: E'mai(: Consu(tation Hours: Office: COURSE DESCRIPTION: ORGCHE1 )Organic Chemistry for Chemistry majors* is a #'unit (ecture course that inc(u&es a re+ie, of -asic .rinci.(es/ nomenc(ature/ as ,e(( as structure an& reacti+e sites of organic mo(ecu(es" It a(so &iscusses the &ifferent forms of isomerism/ conformations an& configurations of organic com.oun&s" $he .hysica( an& chemica( .ro.erties of a(0anes/ a(0y( ha(i&es/ a(0enes/ an& a(0ynes are &iscusse& in more &etai(s" LEARNING OUTCOMES (LO): On com.(etion of the course/ the stu&ent is e1.ecte& to -e a-(e to &o the fo((o,ing: ELGA LEARNING OUTCOME Critica( an& Creati+e $hin0er 2se e(ectronic effects )hy.erconjugation/ in&ucti+e effect/ an& resonance* an& structura( effects )steric effect* to .re&ict chemica( -eha+iors of organic com.oun&s" Recogni3e the functiona( grou.s .resent in an organic com.oun& Pre&ict the mo(ecu(ar geometry of com.oun&s using the 4a(ence She(( E(ectron Pair Re.u(sion )4SEPR* Mo&e( Pre&ict the 0in&s an& re(ati+e strengths of e(ectrostatic forces -et,een mo(ecu(es an& estimate .hysica( .ro.erties such as me(ting .oint/ -oi(ing .oint an& so(u-i(ity -ase& on .o(arity an& sha.e of organic mo(ecu(es" 5etermine the re(ati+e aci&ity of organic com.oun&s -ase& on their chemica( structures" Recogni3e chira( mo(ecu(es an& rea(i3e that a sma(( &ifference in orientation great(y affects their set of .ro.erties" 5ra, sim.(e three &imensiona( mo(ecu(ar formu(as of stereoisomers an& &istinguish -et,een conformation/ configuration/ an& the &ifferent isomeric forms" I&entify the most (i0e(y mechanism of a reaction an& .re&ict the .ro&uct -y consi&ering the factors affecting S !/ S 1/ E!/ an& E1 reactions" I&entify the factors affecting the sta-i(ity of organic mo(ecu(es" Out(ine a synthesis for sim.(e a(0enes an& a(0ynes" Effecti+e Communicator 6rite/&ra, mo(ecu(ar structures using the -on&'(ine/ con&ense& an& &ash structura( formu(as of organic com.oun&s" Gi+e the systematic )I2P%C* an& common names of organic com.oun&s" 2se the )E*')7* system for &esignating a(0ene &iastereomers" Pro.ose synthetic ste.s in the .re.aration of a(0anes an& a(0enes" 2se cur+e& arro,s to i((ustrate the mechanism of a reaction Sho, .atience/ .erse+erance an& &i(igence in ans,ering .ro-(em sets an& e1ercises" Re(ate some of the organic reactions to in&ustria( an& (ife .rocesses" incor.orate 0no,(e&ge gaine& in .ursuits for the im.ro+ement of hea(th an& ,e(('-eing of the community

8ife(ong 8earner

Ser+ice 5ri+en Citi3en

FINAL COURSE OUTPUT: %s e+i&ence of attaining the a-o+e (earning outcomes/ the stu&ent is require& to gi+e a LEARNING OUTCOME REQUIRED OUTPUT 8O 1: 2se e(ectronic effects )hy.erconjugation/ $,o to three minute .resentation in c(ass a-out a s.ecific organic in&ucti+e effect/ an& resonance* or structura( com.oun& of interest containing effects )steric effect* to .re&ict chemica( -eha+iors of organic com.oun&s an& recogni3e an assigne& functiona( grou." $he re.ort shou(& contain -oth ho, e1tensi+e(y organic su-stances affect .hysica( an& chemica( .ro.erties human (i+es an& the en+ironment" of the com.oun&s" RUBRIC FOR ASSESSMENT: Criterion Ver S!ti"#!$tor %& Organi3ation Presentation is ,e(( organi3e& an& com.(ete Scientific Scientific %ccuracy information or facts .resente&/cite& are 1::; accurate" Presentation Presentation is +ery (i+e(y an& interesting" $he stu&ent ,as a-(e to ans,er a(( questions from the c(ass"

DUE DATE 6ee0 9 on,ar&s )one or t,o stu&ents .resenting in a meeting*

Goo'%( Presentation is organi3e& -ut not com.(ete Scientific information or facts .resente&/cite& sho, some inaccuracies" Presentation is (i+e(y an& generates the interest of the +ie,er" $he stu&ent ,as a-(e to ans,er some questions from the c(ass"

S!ti"#!$tor %) Presentation is not organi3e&/ -ut com.(ete" Scientific information or facts .resente&/cite& sho, a significant num-er of inaccuracies" Presentation is not that (i+e(y -ut generates the interest of the +ie,er" $he stu&ent ,as a-(e to ans,er some questions from the c(ass

Nee'" I*+ro,e*ent%Presentation is not organi3e& an& incom.(ete" Scientific information or facts .resente& or cite& are a(( inaccurate" Presentation is -oring/ &oes not generate the interest of the +ie,er/ an& the stu&ent ,as not a-(e to ans,er questions from the c(ass

OT.ER REQUIREMENTS AND ASSESSMENTS: %si&e from the fina( out.ut/ the stu&ent ,i(( -e assesse& at other times &uring the term -y the fo((o,ing: 6ritten E1ams Home,or0/Pro-(em Sets GRADING SYSTEM: $he stu&ent ,i(( -e gra&e& accor&ing to the fo((o,ing: 8ong E1ams Pro-(em Sets/=ui33es/Presentation/Seat,or0/>oar&,or0 ?ina( E1am Passing Gra&e Gra&ing Sca(e <:'<9"@ A<9"@'@1"B A@1"B'@@"1 <:; Gra&e 1": 1"9 !": A@@"1'C!"C ACC"9'DB"! ACC"9'DB"! ADB"!'1:: !"9 #": #"9 B":

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LEARNING PLAN: LEARNING OUTCOME TOPIC C2!+ter -:Intro'3$tion to Or4!ni$ C2e*i"tr 1"1 Organic Chemistry an& 8ife 1"1% $he 5e+e(o.ment of Organic Chemistry as a Science 1"! Structura( $heory of Organic Chemistry 1"# $he Im.ortance of Structura( ?ormu(as:Isomers C2!+ter -:B!"i$ Prin$i+5e" 1"B Chemica( >on&s: $he Octet ru(e 1"9 6riting 8e,is Structures 1"@ ?orma( Charge 1"C Resonance $heory 1"1: %tomic Or-ita(s an& E(ectron Configuration 1"11 Mo(ecu(ar Or-ita(s 1"1! s.# Hy-ri&i3ation: Structure of Methane an& Ethane 1"1# s.! Hy-ri&i3ation: Structure of Ethene 1"1B s. Hy-ri&i3ation: Structure of Ethyne 1"1@ Mo(ecu(ar Geometry: $he 4SEPR $heory 1"1C Re.resentation of Structura( ?ormu(as /EE0 NO1 6ee0 1 LEARNING ACTIVITIES 8ecture Seat,or0 >oar& ,or0

2se the .erio&ic ta-(e to com.are the re(ati+e e(ectronegati+ity of one e(ement ,ith another an& &etermine the forma( charge of an atom or ion" Pre&ict the three &imensiona( structure of mo(ecu(es using the 4a(ence She(( E(ectron Pair Re.u(sion Mo&e( Recogni3e the functiona( grou.s .resent in a gi+en structura( formu(a Pre&ict the 0in& an& re(ati+e strength of e(ectrostatic forces -et,een mo(ecu(es an& .re&ict the .hysica( .ro.erties of organic com.oun&s"

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C2!+ter ): F3n$tion!5 4ro3+" !n' Inter*o5e$35!r For$e" !"1 Car-on'car-on co+a(ent -on&s !"! Hy&rocar-ons: %(0anes/ %(0enes/ %(0ynes an& %romatic !"# Po(ar Co+a(ent >on&s !"B Po(ar an& on.o(ar Mo(ecu(es !"9"!"1# ?unctiona( Grou.s !"1B'!"19 Physica( Pro.erties an& Mo(ecu(ar Structure

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" 5etermine the most re(ati+e aci&ity of organic com.oun&s -ase& on chemica( structures"

%..(y the Internationa( 2nion of Pure an& %..(ie& Chemistry )I2P%C* ru(es in naming organic com.oun&s I&entify the factors affecting the sta-i(ity of a(0anes

C2!+ter (: A$i'" !n' B!"e": Intro'3$tion to Or4!ni$ Re!$tion" !n' Me$2!ni"*" #"1 Reactions an& $heir Mechanisms #"! %ci&'>ase Reactions #"# Car-ocations an& Car-anions #"B $he 2se of Cur+e& arro,s in i((ustrating Reactions #"9 $he Strength of %ci&s an& >ases #"< Pre&icting the Outcome of %ci&'>ase Reactions #"@ Re(ationshi. -et,een structure an& an& %ci&ity #"1:"#"11 $he %ci&ity of Car-o1y(ic %ci&s: #"1# % Mechanism for an Organic Reaction E6!*C2!+ter &: No*en$5!t3re !n' Con#or*!tion" o# A57!ne" B"1 Intro&uction to %(0anes an& Cyc(oa(0anes B"! Sha.es of %(0anes B"# I2P%C nomenc(ature of %(0anes/ %(0y( Ha(i&es an& %(coho(s B"B omenc(ature of Cyc(oa(0anes B"9 omenc(ature of %(0enes an& Cyc(oa(0enes B"< omenc(ature of %(0ynes B"@ Physica( Pro.erties of %(0anes an& Cyc(oa(0anes B"C Sigma >on&s an& >on& Rotation B"D Conformationa( %na(ysis of >utane B"1: Re(ati+e Sta-i(ities of Cyc(oa(0anes: Ring Strain B"11 Conformations of Cyc(ohe1ane B"1! Su-stitute& Cyc(ohe1anes: %1ia( an& Equatoria( Hy&rogen %toms

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B"1# Recogni3e chira( mo(ecu(es an& rea(i3e that a sma(( &ifference in orientation great(y affects its .otency an&/or to1icity" 5ra, sim.(e three &imensiona( mo(ecu(ar formu(as of stereoisomers" &istinguish -et,een conformation/ configuration/ an& the &ifferent isomeric forms" ame chira( mo(ecu(es using the Cahn'Ingo(&'Pre(og system"

Su-stitute& Cyc(oa(0anes:Cis an& $rans Isomerism 6ee0 D 8ecture Po,er.oint Presentation Seat,or0 >oar& ,or0

I&entify the most (i0e(y mechanism of a reaction an& .re&ict the .ro&uct -y consi&ering the factors affecting S !/ S 1/ E!/ an& E1 reactions"

6rite reaction mechanisms using cur+e& arro,s to e1.(ain the con+ersion of one organic com.oun& to another"

2se the )E*')7* system for &esignating a(0ene &iastereomers Confi&ent(y sho, the synthetic ste.s in the .re.aration of organic mo(ecu(es using mo(ecu(ar structures"

C2!+ter 8: Stereo$2e*i"tr : C2ir!5 Mo5e$35e" 9"1 Chira(ity an& stereochemistry 9"! Isomerism: Constitutiona( Isomers an& Stereoisomers 9"# Enantiomers an& Chira( Mo(ecu(es 9"< $ests for Chira(ity: P(ane of Symmetry 9"@ aming of Enantiomers: $he R/S System 9"C Pro.erties of Enantiomers: O.tica( %cti+ity 9"D $he Origin of O.tica( %cti+ity 9"1: $he Synthesis of Chira( Mo(ecu(es 9"11 Chira( 5rugs 9"1! Mo(ecu(es ,ith More than One Chira(ity Center 9"1# ?ischer Projection ?ormu(as 9"1B Stereoisomerism of Cyc(ic Com.oun&s 9"19 Re(ating Configurations through Reactions in ,hich o >on&s to the Chira(ity Center are >ro0en 9"1< Se.aration of Enantiomers 9"1@ Com.oun&s ,ith Chira(ity Centers Other than Car-on 9"1C Chira( Mo(ecu(es $hat 5o ot Possess a Chira(ity Center E6!*) C2!+ter 9: Ioni$ Re!$tion" <"1 Organic Ha(i&es: Physica( Pro.erties <"! uc(eo.hi(ic Su-stitution Reactions <"# uc(eo.hi(es <"B 8ea+ing Grou.s <"9 S ! Reaction <"< % Mechanism for the S ! Reaction <"@ $ransition State $heory: ?ree Energy 5iagram <"C $he Stereochemistry of S ! Reactions <"D S 1 Reaction <"1: % Mechanism for the S 1 Reaction <"11 Car-ocations <"1! $he Stereochemistry of S 1 Reactions <"1# ?actors %ffecting the Rates of S 1 an& S ! Reactions <"1B Organic Synthesis: ?unctiona( Grou. $ransformations 2sing S ! Reactions <"19 E(imination Reactions of %(0y( Ha(i&es <"1< $he E! Reaction <"1@ $he E1 Reaction <"1C Su-stitution +s E(imination C2!+ter :A57ene" !n' A57 ne" P!rt @"! $he )E*')7* System for 5esignating 5iastereomers @"# Re(ati+e Sta-i(ities of %(0enes @"B Cyc(oa(0enes @"9 Synthesis of %(0enes +ia E(imination Reactions @"< 5ehy&roha(ogenation of %(0y( Ha(i&es @"@ %ci& Cata(y3e& 5ehy&ration of %(coho(s @"C Car-ocation Sta-i(ity an& Occurrence of Mo(ecu(ar Rearrangements @"D $he %ci&ity of $ermina( %(0ynes @"1: Synthesis of %(0ynes -y E(imination Reactions @"11 Re.(acement of the %cety(enic Hy&rogen %tom of $ermina( %(0ynes @"1! %(0y(ation of %(0yni&e %nions @"1# Hy&rogenation of %(0enes @"19 Hy&rogenation of %(0ynes E6!* (

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REFERENCES: Te6t;oo7: So(omons/ G"$"6"E ?ryh(e/ C" >" Organic Chemistry/ 1:th E&"E Fohn 6i(ey G Sons )%sia* Pte 8t&: 2S%/ )<--" McMurry/ F" Organic Chemistry/ @th E&"E >roo0s/Co(e/ $homson 8earning/ Inc": 2S%/ )<<=1 6a&e/ 8"G" Organic Chemistry/ @th E&"E Prentice Ha(( Internationa(: e, Fersey/ )<<>1 Carey/ ?"E Giu(iano/ R" Organic Chemistry/ Cth E&"E Mc Gra,'Hi((: 2S%/ )<-Smith/ F"G" Organic Chemistry/ Cth E&"E Mc Gra,'Hi((: 2S%/ )<-ONLINE RESOURCES: So(omons/ ?ryh(e: Organic Chemistry, 10th Edition stu&ent com.anion site" Retrie+e& May 1D/ !:11 from 2tt+:%%;$"1?i5e 1$o*%2e@;$"%Boo7"A!$tionBin'e6C;$"I'B889)Cite*I'B<&:<&<-&-> On'8ine 8earning Center for HOrganic ChemistryH )?rancis %" Carey*" Retrie+e& May 1D/ !:11 from 2tt+:%%???1*22e1$o*%+2 ""$i%$2e*i"tr %$!re 8e% CLASS POLICIES: 1" Stu&ents are require& to su-mit their .ro-(em sets an& assignments on time" !" $hey are a(so require& to ta0e ,ritten e1aminations as sche&u(e&" ?ai(ure to ta0e an e1am on the sche&u(e& &ate ,i(( resu(t in a gra&e of 3ero in the (ong e1am" Ma0e'u. e1am ,i(( -e gi+en for officia( a-sence on(y )58S2'Mani(a stu&ent han&-oo0*" #" E1ce.t those stu&ents in the 5eanIs 8ist/ stu&ents e1cee&ing more than 9 a-sences ,i(( automatica((y get a fina( gra&e of :":"

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