Organic Chemistry

Organic Chemistry:Organic Chemistry:Study of carbon based moleculesStudy of carbon based molecules

BondingBonding

Covalent (share valence e-)Covalent (share valence e-)

All NonmetalsAll Nonmetals

Made of Made of carbon,carbon, hydrogenhydrogen and other and other

nonmetals like sulfur, oxygen, nitrogen etcnonmetals like sulfur, oxygen, nitrogen etc..

Carbon Based MoleculesCarbon Based Molecules

Carbon Atoms Form the “Backbone”Carbon Atoms Form the “Backbone”

Carbon has 4 valence and needs 4 moreCarbon has 4 valence and needs 4 more

ALWAYSALWAYS forms 4 bonds forms 4 bonds

Bonds can be single, double or tripleBonds can be single, double or triple

Due to variety and number Due to variety and number

of bonds carbon can form of bonds carbon can form

you can have an enormous you can have an enormous

number of combinationsnumber of combinations

Properties of Organic Properties of Organic CompoundsCompounds

Melting Point Temp.Melting Point Temp.Relatively Low MPRelatively Low MP (compared to ionic, metallic)(compared to ionic, metallic)

MP depends on strength of IMF MP depends on strength of IMF

Non-polar moleculesNon-polar molecules: (Lowest MP): (Lowest MP)Have VDW attractions (weak)Have VDW attractions (weak)Larger NP molecules have higher MP than smallerLarger NP molecules have higher MP than smaller

Polar moleculesPolar molecules: (Slightly Higher MP): (Slightly Higher MP)Dipole-dipole attractions or H-bonding Dipole-dipole attractions or H-bonding Molecules held together moreMolecules held together more

SolubilitySolubility

Polar molecules:Polar molecules: soluble in polar solvents like watersoluble in polar solvents like water

Nonpolar molecules:Nonpolar molecules: soluble in nonpolar solvents like hexanesoluble in nonpolar solvents like hexane

Look for:Look for: Symmetry = nonpolarSymmetry = nonpolar Assymmetry = polarAssymmetry = polar

Conductivity in SolutionConductivity in Solution

Organic Molecules usually DO NOT ionizeOrganic Molecules usually DO NOT ionizedon’t conduct in solutiondon’t conduct in solution

NONELECTROLYTESNONELECTROLYTES

Important Exception:Important Exception: ORGANIC ACIDSORGANIC ACIDS

Ex: CHEx: CH33COOHCOOH

Also…Also…

Organic Molecules:Organic Molecules:Undergo combustionUndergo combustion in the presence of in the presence of oxygenoxygen

Slow rates of reactionSlow rates of reaction due to complexity of due to complexity of bonds (often catalyst needed)bonds (often catalyst needed)

Breakdown/decompose at low temperatureBreakdown/decompose at low temperature compared to other compoundscompared to other compounds

Formula Writing and Formula Writing and Drawing MoleculesDrawing Molecules

Types of FormulasTypes of Formulas

MolecularMolecularEmpiricalEmpiricalStructuralStructural

Condensed StructuralCondensed Structural

Organic Prefixes (Table P)Organic Prefixes (Table P)MethMethEthEth

PropPropButButPentPentHexHexHeptHeptOctOctNonNonDecDec

Indicate how many carbon atoms are in the entire moleculeIndicate how many carbon atoms are in the entire moleculeYou will only see molecules with a max of 10 carbonsYou will only see molecules with a max of 10 carbons

Homologous Series of Homologous Series of Hydrocarbons (Table Q)Hydrocarbons (Table Q)

Have unique general “formula”Have unique general “formula”Each member of the series differs by oneEach member of the series differs by one

carbon and a certain # of hydrogencarbon and a certain # of hydrogen

AlkanesAlkanes

General Formula:General Formula: CCnnHH2n+22n+2

All All singlesingle bonds between carbon atoms bonds between carbon atoms

Name ends in “ane”Name ends in “ane”

SATURATEDSATURATED hydrocarbons hydrocarbons(holding as many hydrogen atoms as possible)(holding as many hydrogen atoms as possible)

http://www.kentchemistry.com/links/organic/orgonaming1.htm

AlkenesAlkenes

General Formula:General Formula: CCnnHH2n2n

One One doubledouble carbon to carbon bond carbon to carbon bond

*Address needed for bond location*Address needed for bond location

Name ends in “ene”Name ends in “ene”

UNSATURATED UNSATURATED hydrocarbonshydrocarbons(not totally filled with hydrogen)(not totally filled with hydrogen)


AlkynesAlkynes

General Formula: General Formula: CCnnHH2n-22n-2

One One tripletriple carbon to carbon bond carbon to carbon bond

*Address needed for bond location*Address needed for bond location

Name ends in “yne”Name ends in “yne”

UNSATURATED UNSATURATED hydrocarbonshydrocarbons(not totally filled with hydrogen)(not totally filled with hydrogen)


dienes, diynes etc…dienes, diynes etc…

Have multiple double or triple bonds.Have multiple double or triple bonds.

Give the address for each multiple bond.Give the address for each multiple bond.

End of name becomes “-diene…or –triene”End of name becomes “-diene…or –triene”

Use prefix “di/tri/tetra/penta” etc…if more Use prefix “di/tri/tetra/penta” etc…if more than one of the same thing on the chain.than one of the same thing on the chain.

http://www.kentchemistry.com/links/organic/orgonaming5.htmhttp://www.kentchemistry.com/links/organic/orgonaming6.htm

Branching HydrocarbonsBranching Hydrocarbons

Have hydrocarbon “branches” off the main Have hydrocarbon “branches” off the main carbon chain.carbon chain.

Called Called “alkyl” groups“alkyl” groups

Naming Branched HydrocarbonsNaming Branched Hydrocarbons

Find longest continuous carbon chain and Find longest continuous carbon chain and name itname it (parent chain)(parent chain)

Find address of each branch Find address of each branch

Count carbons in each branchCount carbons in each branch

Name branches using prefix ending in “yl”Name branches using prefix ending in “yl” Ex: 2 carbon branch would be an “ethyl” branch.Ex: 2 carbon branch would be an “ethyl” branch.

NoteNote: : If more than one of the same type of branch use If more than one of the same type of branch use ““di”, “tri”, “tetra” etc…instead of repeating the namedi”, “tri”, “tetra” etc…instead of repeating the name

IsomersIsomers

Same molecular formulas, but different Same molecular formulas, but different structural formulasstructural formulas..

Atoms in the molecule have a different Atoms in the molecule have a different arrangement.arrangement.

The more atoms the larger the number of The more atoms the larger the number of possible isomers possible isomers

http://www.kentchemistry.com/links/organic/isomersofalkanes.htm

Cyclical HydrocarbonsCyclical Hydrocarbons

Form ringsForm rings

Start with “cyclo-”Start with “cyclo-”


Benzene SeriesBenzene Series

Benzene SeriesBenzene Series::6 carbon ring with alternating double bonds.6 carbon ring with alternating double bonds.

Electrons in double bonds “resonate” between Electrons in double bonds “resonate” between bond sites giving more strength to all the bondsbond sites giving more strength to all the bonds

Branches and functional groups are often Branches and functional groups are often attached to the ringattached to the ring

Ortho/Meta/Para locationsOrtho/Meta/Para locations


Organic Functional GroupsOrganic Functional GroupsReference Table RReference Table R

HalidesHalides

Contain one or more halogen atoms.Contain one or more halogen atoms.

Fluoro / chloro / bromo / iodo prefixFluoro / chloro / bromo / iodo prefix

Use address Use address

Use di, tri, tetra if more than one of sameUse di, tri, tetra if more than one of same

http://www.kentchemistry.com/links/organic/halides.htm

AlcoholsAlcohols

Have one or more Have one or more “Hydroxyl” groups (-OH)“Hydroxyl” groups (-OH)

Use address

Name ends in “-ol”

If more than one (–OH), name ends in “diol”, or “triol”

Important Example: Glycerol or 1, 2, 3 propantriolImportant Example: Glycerol or 1, 2, 3 propantriol

Types of AlcoholsTypes of Alcohols

PrimaryPrimary

SecondarySecondary

TertiaryTertiary

http://www.kentchemistry.com/links/organic/alcohols.htm

Aldehydes Aldehydes

Carbon double bonded to oxygen Carbon double bonded to oxygen at endat end

of a carbon chain (“carbonyl” group)of a carbon chain (“carbonyl” group)

ADDRESS NOT NEEDED (always at end!)ADDRESS NOT NEEDED (always at end!)

End in “–al”End in “–al”

http://www.kentchemistry.com/links/organic/Aldehydes.htm

KetonesKetones

Carbon double bonded to oxygen Carbon double bonded to oxygen in middlein middle of a carbon chain (“carbonyl” group)of a carbon chain (“carbonyl” group)

Use addressUse address

End in “-one”End in “-one”

http://www.kentchemistry.com/links/organic/Ketones.htm

EthersEthers

Oxygen atom withinOxygen atom within carbon chain carbon chain

Count carbon atoms on either side of oxygen Count carbon atoms on either side of oxygen and name them like “alkyl” branches.and name them like “alkyl” branches.

““Butterflies” with belly buttonsButterflies” with belly buttons

http://www.kentchemistry.com/links/organic/ethers.htm

Organic AcidsOrganic Acids

At the endAt the end of the carbon chain is a “carboxyl” of the carbon chain is a “carboxyl” group containing two oxygen atoms.group containing two oxygen atoms.

ADDRESS NOT NEEDEDADDRESS NOT NEEDED (always at end!) (always at end!)

End in “-oic acid”End in “-oic acid”

Has an acidic hydrogen that ionizes so these are Has an acidic hydrogen that ionizes so these are ELECTROLYTESELECTROLYTES

http://www.kentchemistry.com/links/organic/OrgAcid.htm

EstersEsters

WithinWithin the chain, there is an oxygen atom that is the chain, there is an oxygen atom that is next to a carbon double bonded to oxygennext to a carbon double bonded to oxygen

Use oxygen inside of chain as middle point. (Sorta Use oxygen inside of chain as middle point. (Sorta like an “ether” belly button)like an “ether” belly button)

Name both sides around the oxygen atomName both sides around the oxygen atom Side with carbon “Alkyl” branch, Side with carbon “Alkyl” branch, ends in “yl”ends in “yl” Side with the double bonded oxygen Side with the double bonded oxygen ends in “oate”ends in “oate”

http://www.kentchemistry.com/links/organic/esters.htm

AminesAmines

Have an “amine” group containing Have an “amine” group containing nitrogennitrogen..

Use addressUse address

Ends in “-amine”Ends in “-amine”

Important Example: Amino AcidImportant Example: Amino Acid

http://www.kentchemistry.com/links/organic/amines.htm

AmidesAmides

Also have a Also have a nitrogen nitrogen atom, but it is next atom, but it is next to a carbon double bonded to oxygen.to a carbon double bonded to oxygen.

End in “amide”.End in “amide”.

http://www.kentchemistry.com/links/organic/amide.htm

Organic ReactionsOrganic Reactions

CombustionCombustion

Burning or oxidation of a hydrocarbon.Burning or oxidation of a hydrocarbon.Needs ONeeds O22

Produces COProduces CO22 and H and H22OOAlways EXOTHERMICAlways EXOTHERMIC

If not enough OIf not enough O22 present, you can get present, you can get

“incomplete” combustion resulting in “incomplete” combustion resulting in carbon monoxide (CO) and soot (C).carbon monoxide (CO) and soot (C).

http://www.kentchemistry.com/links/organic/combustion.htm

FermentationFermentation

Makes ALCOHOL!!!Makes ALCOHOL!!!

Sugar is metabolized by yeast enzymes to Sugar is metabolized by yeast enzymes to make ethanol and COmake ethanol and CO22

http://www.kentchemistry.com/links/organic/Fermentation.htm

SubstitutionSubstitution

Happens with Happens with ALKANESALKANES One hydrogen atom comes off and is One hydrogen atom comes off and is

“substituted” for another atom.“substituted” for another atom.Results in Results in TWO productsTWO products

Ex: Halogen SubstitutionEx: Halogen Substitution

http://www.kentchemistry.com/links/organic/Substituition.htm

AdditionAdditionALKENESALKENES and and ALKYNESALKYNES..Add atoms without removing hydrogenAdd atoms without removing hydrogenDouble or triple bond “opens up” Double or triple bond “opens up” Two atoms “add on” for each broken bondTwo atoms “add on” for each broken bondResults in Results in ONE productONE product..Ex:Ex:

Halogen AdditionHalogen AdditionHydrogenationHydrogenation

http://www.kentchemistry.com/links/organic/Addition.htm

PolymerizationPolymerizationJoining together of many individual “monomers” toJoining together of many individual “monomers” tomake a “polymer”.make a “polymer”.

Ex: Synthetic PolymersEx: Synthetic Polymers NylonNylon RayonRayon PolyethelenePolyethelene Polystyrene (styrofoam)Polystyrene (styrofoam) PolyesterPolyester

Ex: Natural PolymersEx: Natural Polymers DNA/RNADNA/RNA Starch, CelluloseStarch, Cellulose ProteinsProteins

http://www.kentchemistry.com/links/organic/polymers.htmhttp://www.kentchemistry.com/links/organic/polymersswf.htm

Types of PolymerizationTypes of Polymerization

Condensation PolymerizationCondensation PolymerizationRemove water to join monomersRemove water to join monomersEx: Amino Acids joining to make “peptide” bondsEx: Amino Acids joining to make “peptide” bonds

Addition PolymerizationAddition PolymerizationOpen up double/triple bonds to join monomersOpen up double/triple bonds to join monomersHappens to alkenes/alkynesHappens to alkenes/alkynes

http://www.kentchemistry.com/links/organic/polymerization.htm

CrackingCracking

BreakingBreaking of long hydrocarbon chains into of long hydrocarbon chains into smaller ones.smaller ones.

Often used on long chain hydrocarbons Often used on long chain hydrocarbons found in petroleum to make them into found in petroleum to make them into more usable fuels.more usable fuels.

Usually involves a catalystUsually involves a catalyst

http://www.kentchemistry.com/links/organic/cracking.htm

Fractional DistillationFractional Distillation

Separation of a petroleum mixture by Separation of a petroleum mixture by differences in Boiling Pointdifferences in Boiling Point temperature. temperature.

Most compounds in petroleum are non-Most compounds in petroleum are non-polar hydrocarbons.polar hydrocarbons.

Larger chains = stronger VDW = higher BPLarger chains = stronger VDW = higher BP

Smaller chains = weaker VDW = lower BPSmaller chains = weaker VDW = lower BP

http://www.kentchemistry.com/links/organic/Fractional.htm

***Esterification******Esterification***

Dehydration synthesis (water is removed to Dehydration synthesis (water is removed to join molecules)join molecules)

Alcohol + Organic Acid Alcohol + Organic Acid Ester + Water Ester + Water

Ester molecules often have nice Ester molecules often have nice odorsodorsFatsFats are a type of ester made of glycerol and are a type of ester made of glycerol and

3 fatty acid chains3 fatty acid chains

http://www.kentchemistry.com/links/organic/esterfication.htm

Saponification Saponification (Making Soap)(Making Soap)

Soap molecules are long molecules that Soap molecules are long molecules that are nonpolar at one end and polar at the are nonpolar at one end and polar at the other end.other end.

Can bring oil and water togetherCan bring oil and water together

Ester + Base Ester + Base Soap + GlycerolSoap + Glycerol

http://www.kentchemistry.com/links/organic/saponification.htm

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Organic Chemistry