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1
Organic Chemistry
Chapter 20
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Carbon
All living matterFour bondsDouble and triple bonds
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Diamond
Colorless crystalline solidExtremely high melting pointConducts heat very wellDoes not conduct electricityCovalent network bonding
Bonded to four nearest neighbors
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Graphite
Crumbles easilyFeels greasyAtoms arranged in thin layersWeak London dispersion forces
Layers slide past each other
Conducts electricity
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Fullerenes
Formed when carbon-containing materials are burned with limited oxygenNearly sphericalC60
Most stableCalled buckminsterfullerene or buckyball
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Organic compounds
Covalently bonded compounds containing carbonExcept:
Carbonates and oxides
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Catenation
Covalent bonding of an element to itself to form chains or rings
Carbon can also double or triple bond to itself
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hydrocarbons
Contain only carbon and hydrogenSimplest organic compounds
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Structural formula
Regular or condensed
Carbon makes four bonds, hydrogen makes oneHydrogen is understood to bond to the atom next to it
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Draw the condensed structural formulas
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Geometric isomers
Order of atom bonding is the same, but arrangement of atoms is space is differentNeed rigid structure in molecule
Double or triple bond
Need two carbons each with two different groups attachedCis and trans isomers
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Cis isomer
Like groups on same side of carbon atoms
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Trans iosmer
Like groups on opposite sides of carbon atoms
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Alkanes
AKA saturated hydrocarbonsHold maximum amount of hydrogenContain only single bondsGeneral formula CnH2n+2
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Cycloalkanes
Carbons arranged in ringFewer hydrogen atoms – no free endsGeneral formula CnH2n
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propane vs. cyclopropane
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Simplified cycloalkane structure
Carbon at each cornerEnough hydrogen so each carbon has four bonds
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IUPAC
International Union of Pure and Applied ChemistrySystematic naming system
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Unbranched chain alkanes
Count carbon atoms for prefixTable 20-3, page 636
And suffix -ane
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You try
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Branched-chain alkanes
Branches are alkyl groupsTable 20-4, page 637
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Alkane nomenclature
1. Name the parent hydrocarbonLongest continuous carbon chainMight be bentName as straight-chain alkane
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Alkane nomenclature
2. Add the names of the alkyl groupsIn frontalphabetizeAdd prefixes if necessary (di-, tri-, tetra-, penta-, etc.)
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Alkane nomenclature
3. Number the carbon atoms in parent alkaneGive lowest numbers to alkyl groupsIf two possibilities, make the first alkyl group in name have lowest number
4. Insert position numbersBefore alkyl group names
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Alkane nomenclature
5. PunctuateHyphens between numbers and namesCommas between numbers
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You try
Name the molecule aboveoctane
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You try
Name the molecule above3-ethyl-2,4,5-trimethyloctane
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You try
Name the molecule above5-butyl-2,2-dimethylnonane
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Example
Draw the condensed structural formula for 3,3,4-triethyl-4-methylhexane.
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You try
Draw the condensed structural formula for 3-ethyl-2,2-dimethylpentane.
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Alkenes
Unsaturated hydrocarbonsHave at least one double bond
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Alkene nomenclature
1. Name the parent hydrocarbonLongest continuous carbon chain containing double bondMight be bentAdd suffix –ene if only one double bond
If two, -adieneThree, - atrieneEtc.
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Alkene nomenclature
2. Add the names of the alkyl groups3. Number the carbon atoms in parent alkene
First carbon in double bond nearest end of chain has lowest numberIf two possibilities, number from end nearest first alkyl groups
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Alkene nomenclature
4. Insert position numbersDouble-bond position numbers before parent alkene nameBefore alkyl group names
5. Punctuate
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Example
Name the following alkene.
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You try
Name the following alkene
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You try
Draw 1,3-butadiene
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Alkynes
Contain at least one triple covalent bond.
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Alkyne nomenclature
1. Name the parent hydrocarbonLongest continuous carbon chain containing triple bondMight be bentAdd suffix –yne if only one triple bond
If two, -adiyneThree, - atriyneEtc.
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Alkyne nomenclature
2. Add the names of the alkyl groups3. Number the carbon atoms in parent alkyne.
First carbon in triple bond nearest end of chain has lowest numberIf two possibilities, number from end nearest first alkyl groups
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Alkyne nomenclature
4. Insert position numbersTriple-bond position numbers before parent alkyne nameBefore alkyl group names
5. Punctuate
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You try
Name the following compound
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You try
Draw 3,3-dimethyl-1-butyne
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Aromatic hydrocarbons
Contain six-membered benzene ringDelocalized electrons
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Aromatic hydrocarbon nomenclature
1. Name the parent hydrocarbonBenzene
2. Add the names of the alkyl groups3. Number the carbon atoms in ring
1 goes with alkyl group that comes first alphabeticallyNumber in the direction that gives the rest of the groups the lowest numbers
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Aromatic hydrocarbon nomenclature
4. Insert position numbers5. Punctuate
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You try
Name the following compound
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You try
Draw 1-ethyl-2-methylbenzene