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NCSU CH 221 - 221cam8-L1-skeletal

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11Organic molecules© Dr. Kay SandbergWhich of these organic molecules have you ingested today?CH3CH2OHHNCNCCCOOCH3NCHNCH3NCNCCCOH3COCH3NCHNCH32What do you see?© Dr. Kay SandbergNN3You are a walking organic lab© Kay SandbergNorepinephrineHOHOOHNH2Adrenaline (epinephrine)HOHOOHNHCH3SN2-H+4Organic chemistry overviewCH221: Organic ChemistryOrganic ChemistryPart oneOverviewHydrocarbons:Hydrocarbons:•alk___•alk___•alk___©Dr. Kay Sandberg5Organic ReactionsCH221: Organic ChemistryOrganic ChemistryPart oneOverviewBasic reactions & mechanisms:Basic reactions & mechanisms:•Nucleophilic Substitution rxns: SN1 & SN2•Elimination rxns: E1 & E2•Addition rxns©Dr. Kay Sandberg•Radical rxns6Domino effect©Dr. Kay SandbergGet started on the right foot!Strategy for success Understanding lecture workUnderstanding homeworkUnderstanding examsUnderstanding organic chemistry27Will you make an A?©Dr. Kay SandbergStudents who have an A daily average, butfail exams have not progressed past the “what”.Organic chemistry:What?Why?How?8Bond and lone pair #’sHow many bonds does a nonmetal form so that it has access to an octet (where nonmetal’s formal charge is zero)?©Dr. Kay Sandberg_ bonds_ bonds_ bonds_ bond_ bondSection 1.34th family5th family6th family7th family8th familyNCOFNe_ lp_ lp_ lp_ lp_ lp9Lewis structuresSection 1.7Formulas for moleculesOne Lewis structure:CHCHHCHHOHHHC3H8OMolecular formulaMolecular formulaDoes not show the “hook up”order of the atomsCHCHHCHHHHOHAnother Lewis structure:©Dr. Kay SandbergCHOHHCHHCHHH10Condensed structural formula©Dr. Kay SandbergSection 1.7Short cuts for representing the structures of molecules:CHCHHCHHOHHHCHCHHCHHOHHH1) Omit LP2) Omit C-C & C-H bonds(CH3)2CHOH3) Omit all bondsCondensed structural formulaCH3CHCH3OH11Skeletal structureCHCHHCHHOHHHHHHHHHHOH4) Omit C labels5) Omit C labels &C-H bonds & H labels (bonded to C)Skeletal structure©Dr. Kay SandbergShort cuts for representing the structures of molecules:12Skeletal vs LewisSection 1.7Short cuts for representing the structures of molecules:CHCHHCHHOHHH________structureOH©Dr. Kay SandbergOHused prevalently inorganic chemistryused inbiochemistry313JME input formatSection 1.7JME editorinput formatOHOHOHJME editor:Automatically adds HDoes not show LP’sXDo NOT usethe X-tool to input H (protium isotopeof hydrogen)14Condensed to skeletalNHO©Dr. Kay SandbergSection 1.7Draw the skeletal structure for(CH3)2CHCH=OWhat is the molecular formula for:LP#?double bondedoxygen15Condensed to skeletal continuedcondensed structural formula©Dr. Kay SandbergOcean: Draw the skeletal structure of:Section 1.7Each C needs 4 bonds and NO lone pairs.H only forms 1 bond.Hint: the bonds do not all have to be single(you may need to use double or triple bonds)Start C skeleton from left to right16Constitutional isomers__-means “the same”______________cpds with the same molecular formula,but different properties___means “part”____________________________: molecules withthe same molecular formula, but differenthook up orders (connectivities).OH©Dr. Kay SandbergC3H8OHO17©Dr. Kay Sandberg(CH3)2CHOHOHHOOH182-D representationLewis structuresSimplest alkane (CH4)2-D representationHCHHH____aneSection 1.10©Dr. Kay SandbergThis structure does not reflect reality. This molecule does NOTpossess __obond angles.This molecule is NOT_____.What is reality?4193-D representationReality: tetrahedral geometry3-D molecular shape (reality)HCHHHmethaneHCHHHSection 1.10©Dr. Kay SandbergVSEPR (valence shell electron pair repulsion model)20Bonding of methaneHybridizeTetrahedrallydistributedsp3sp3sp3sp3spxpypzC4Hsp3sp3sp3sp3Cs s s sHCHHH_ bond__________ orbitals ________ orbitalsMethane (CH4) bonding HCHHH©Dr. Kay SandbergSection 2.6Each H pure s-orbitaloverlaps with a sp3hybrid C orbital_____ bond21Bond angles in methaneMethaneHHCHHAll carbons are ___hybridized__ C-H σ bondsSection 2.6Alkane: CnH2n+2©Dr. Kay Sandberg_____o22Alkane generic formulaAll carbons are sp3 hybridized in alkanesSection 2.3Alkane: CnH2n+2©Dr. Kay SandbergHow many hydrogens are in an alkane chain composed of 200 carbons?23Bonding of ethaneEthane (C2H6)bonding HCCHHHHH1 C-C σ bondThe C-C σ-bond has a cylindrical shape24Bonding of propaneHCCHCHHHHHHPropane (C3H8)Section 2.7_ C-C σ bond_ C-H σ bonds©Dr. Kay Sandbergskeletal structureWord of warning:Do not use thewedge/dash toolin the JME editoruntil the stereochemistrychapter (or told otherwise)JME input for propane525Functional group definitionOrganic compoundsStructural unit responsible for a givenmolecule’s chemical reactivity under aparticular set of conditions.Structure, reactions & applicationsMillions of compounds Few structural types (classes/families) Few reaction typesClass/Family: characterized by presence of _________ _______Section 2.1©Dr. Kay SandbergFind the patterns!!26Classes of hydrocarbons•Functional group classesClasses of hydrocarbons•Hydrocarbon structural typesChapter 2Section 2.1C-C & C-H bonds_______ _______alkanesC-CalkenesC=CalkynesC CCh 2Ch 5,6Ch 9Ch 11,12(CH223)arenes©Dr. Kay Sandberg27FG transformationR-HFunctional group transformationsCH3CH3+ Cl2CH3CH2Cl + HClchlorine_______________hydrogenchlorideCCHHHHHH+Cl ClCCClHHHHH+H ClR-H + Cl2R-Cl + HCl______________©Dr. Kay Sandberg28Alkane derivativesFunctionally substituted derivatives of alkanesR-OH __________CH3CH2OHR-X __________ CH3CH2Cl(F,Cl,Br,I)R-NH2__________CH3CH2NH2R2CCR2O__________H2CCH2OR-O-R__________ CH3CH2OCH2CH3__________R-C N CH3CH2C NR-NO2__________CH3CH2NO2R-Der ClassExampleR-SH __________ CH3CH2SH©Dr. Kay SandbergR-H (replace H with something else – derivative)29OCHCarbonyl derivativesClasses of cpds that contain a carbonyl groupCH3CH2COHR-DerClassExampleOCHR_________CH3CH2COCH3OCRRCH3CH2COOHOCOHROCOCOHOCOCOCH3CH2COOCH3OCORR©Dr. Kay Sandberg___________________________30FG condensed structural formulaDraw the skeletal structure of the following molecules.©Dr. Kay SandbergA) H2CCHCH2CH2OHB) H2CCHCH2COH©Dr. Kay SandbergWhat is the functional group (FG) in each?How do you know when the CO will be C-O or


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