CHEM 212 - Structures and Geometry Review

IntroductoryOrganicChemistry
Chem 212&Chem 211
ORGANICBITES1A:STRUCTURES&GEOMETRYREVIEW
Dr.LauraPavelka
DepartmentofChemistry
Pulp&Paper104
laura.pavelka@mcgill.ca
FIRST,ABITOFREVIEW...
Section1 OrganicStructures(Review)
Chapter1 BondingandMolecularStructure
OctetRuleandLewisStructures
DrawingOrganicMolecules
Resonance
VSEPRGeometry
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OrganicBites1A Chapter1
ValenceElectrons
Group4=4valenceelectrons
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MakingChemicalBonds
THEOCTETRULE tendencyofanatomtofillvalencewitheightelectrons
(atomsreacttoachievestablenoblegaselectronconfigurations)
1. TRANSFEROFELECTRONS IONICBONDS
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occursbetweenatomsofdifferingelectronegativity
formssalts(ionpairs)
MakingChemicalBonds
1. TRANSFEROFELECTRONS IONICBONDS
occursbetweenatomsofdifferingelectronegativity
formssalts(ionpairs)
ex.Li+F
Li+ +F
ionsachieveHeandNeelectronicconfigurations
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MakingChemicalBonds
2. SHARINGELECTRONS COVALENTBONDS
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occursbetweenatomsofsimilarelectronegativity
formsmolecules(eachbond=2sharedelectrons)
AssigningFormalCharges
1.
2.
3.
Determineneutralvalenceofeachatom
Assigneachatomhalfofbondingelectrons+lonepairs
FC=NeutralValence(1) Assignedelectrons(2)
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AssigningFormalCharges
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DrawingLewisStructures
1.
2.
3.
4.
Valenceelectronsofeachatom?
Anycharges?...NO moveon,...YES add/subtractelectrons
Noblegaselectronicconfigurationateachatom?
Assignformalcharges.
ex.CH6N+
ex.C2H3Cl
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ExceptionstotheOctetRule
1. Elementsofthethirdrowandbelow
havemorethan4valenceorbitals,canholdmorethan8electrons
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ExceptionstotheOctetRule
2. Electrondeficient(reactive)molecules
havelessthan4valenceelectrons,canholdlessthan8electrons
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1.
2.
3.
4.
Noblegaselectronicconfigurationateachatom/knownexception?
ex.SO42
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ex.B2H6
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StructuralFormulaandIsomers
ISOMERS differentcompoundswiththesamemolecularformula
STRUCTURAL/CONSTITUTIONAL differentconnectivity(differentnames)
differentphysicalproperties/reactivity
ex.TWOSTRUCTURESWITHFORUMLAC3H6O
STRUCTURALFORMULAS allbondsexplicitlyshown
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StructuralFormulaandIsomers
ISOMERS differentcompoundswiththesamemolecularformula
STRUCTURAL/CONSTITUTIONAL differentconnectivity(differentnames)
differentphysicalproperties/reactivity
ex.THREESTRUCTURESWITHFORMULAC3H8O
STRUCTURALFORMULAS allbondsexplicitlyshown
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...ANDWENEEDTOMAKESUREWE
REMEMBERHOW TODRAW/INTERPRET
ALLTYPESOFCHEMICALSTRUCTURES
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OrganicBites1A:Structures&GeometryReview
Resonance
VSEPRGeometry
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CondensedFormulas
C4H10
MolecularFormula
StructuralFormula
CH3CH2CH2CH3
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CondensedFormula
17
1.
2.
3.
4.
Noblegaselectronicconfigurationateachatom?
ex.CH3CH2CO2Li
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ex.CH3NCO
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Skeletal(bondline)Structures
StructuralFormula
SkeletalStructure
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StructuralFormula
SkeletalStructure
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StructuralFormula
SkeletalStructure
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HN
O
CH3
HO HO
HO
N
HO
CH3
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OH
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DrawingIsomers
Skeleton:
Condensed:
FullLewis
Structure:
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Practice:SkeletalStructures
DrawcompleteLewisstructures(structuralformula,includinglonepairs)
forthefollowingcompounds:
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Practice:SkeletalStructures
Whichofthefollowingareconstitutionalisomers?
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SOMETIMESONELEWISSTRUCTUREIS
INSUFFICIENTTOACCURATELYDESCRIBE
ASINGLEMOLECULE/ION...
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Resonance
VSEPRGeometry
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ResonanceStructures
*multiplecorrectLewisstructures onlymoveelectrons,notpositionsofatoms*
ResonanceTheory whenamolecule/ionrepresentedby>2Lewisstructures:
1. Noneofthesestructuresarerealisticrepresentationsforthemolecule/ion
2. Actualmolecule/ionisaHYBRIDOFALLRESONANCESTRUCTURES
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RulesforWritingResonanceStructures
1.
2.
3.
4.
Resonancestructuresonlyexistonpaper
ONLYallowedtomoveelectrons bondsareNOTbroken
ALLstructuresmustbevalidLewisstructures.
TheACTUALenergyofamoleculeislowerthananyoneresonancestructure
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1.
2.
3.
4.
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1.
2.
3.
4.
HYBRID
HYBRID
equivalentresonancestructures
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Practice:Resonance
Drawaresonancestructureforeachofthefollowingstructures.
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LEWISSTRUCTURES,CONDENSED
FORUMLA,ANDSKELETALSTRUCTURES
SHOWBONDATTACHMENT...
BUTNOTMOLECULARSHAPE
(GEOMETRY)!
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Resonance
VSEPRGeometry
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VSEPR&TetrahedralGeometry
VSEPR ValenceShellElectronPairRepulsionTheory
*putvalenceelectronpairsasfarapartfromoneanotheraspossible*
TETRAHEDRALGEOMETRY
ex.methane:4electrongroups,4bonds
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DrawingTetrahedralStructures
Skeleton(bondline)structure
3DFormulas
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VSEPR&PyramidalGeometry
PYRAMIDALGEOMETRY
ex.ammonia:4electrongroups,3bonds
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VSEPR&BentGeometry
BENTGEOMETRY
ex.water:4electrongroups,2 bonds
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TetrahedralBasedGeometries
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Remember...GeometryandVSEPR
TRIGONALPLANARGEOMETRY
ex.formaldehyde:3 electrongroups,3bonds
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BENTGEOMETRY
ex.nitriteion:3 electrongroups,2bonds
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LINEARGEOMETRY
ex.carbondioxide:2electrongroups,2bonds
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Practice:Geometry
Whatisthegeometryofeachindicatedatominthefollowingcompound?
HN
O
CH3
HO HO
HO
N
HO
CH3
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OH
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OrganicBites1A:MainObjectives
1. Assignformalchargetoagivenatominamolecule.
2. DrawLewisstructures(structuralformula)given
formula,condensedformula,orskeletalstructures.
3. Identifyanddrawstructural/constitutionalisomers.
4. Drawaccurateresonancestructures.
5. UseVSEPRtheorytopredictthegeometryaboutan
atomcenter.
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CHEM 212 - Structures and Geometry Review

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IntroductoryOrganicChemistry

Chem 212&Chem 211

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