a brief introductionorganic chemistry a brief introduction thursday, april 2, 2009 the study of...
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Organic Chemistry
A brief introduction
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the study of carbon-containing compounds and their properties
Organic Chemistry
excluding: CO, CO2, CS2, carbonates and cyanides
eight million known organic compounds(and counting!)
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Hydrocarbons
compounds composed of hydrogen and carbon
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Alkanes
The simplest hydrocarbon
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Alkanes
CnH2n+2 where n = 1,2,3...
generic chemical formula
a hydrocarbon containing only single covalent bonds
CH4 C
H
HH
H
Methane
sp3 hybridizationthese molecules are said to be saturated, meaning no more hydrogen atoms can be added to the molecule
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Alkanes
CH4Methane
C2H6Ethane CH
HH
CH
HH
CH
HH
H
CH
HH
CH
HCH
HH
C3H8Propane
C4H10Butane Two possible schemes
You must memorize these 1st 4
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n-butane
CH
HH
CH
HCH
HCH
HH C
HH
HCH
CH
HH
H CH
H
Structural Isomers:Molecules that have the same molecular formula
but different constitutions/connectivities
Structural Isomers
Exhibit different chemical and physical properties
isobutane
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Elemental Composition
Empirical Formula
Molecular FormulaConstitution
Configuration
Conformation
Levels of Structure
√√√
the order in which the atoms are connected
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Alkane Nomenclaturethe names of alkanes beyond butane are obtained by
adding the suffix -ane to the Greek root for the number of carbon atoms
(CH2)8 CH3CH3 decane(CH2)7 CH3CH3 nonane(CH2)6 CH3CH3 octane
the longest continuous chain of carbon atoms determines the root name
(CH2)5 CH3CH3 heptane(CH2)4 CH3CH3 hexane(CH2)3 CH3CH3 pentane
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Alkane NomenclatureWhen alkane groups appear as substitutents, they are
named by dropping the -ane and adding -yl.
CH2 CH2CH3 PropylCH2CH3 Ethyl
CH3 Methyl
CH CH3CH3 Isopropyl
CH2 CH2CH3 CH2 Butyl
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Alkane NomenclatureWhen alkane groups appear as substitutents, they are
named by dropping the -ane and adding -yl.
CH2 CHCH3 CH3 sec- Butyl
C CH2CH3
CH3
H
iso-Butyl
C CH3CH3
CH3tert-Butyl
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Alkane NomenclatureThe position of substituent groups are specified by
numbering the longest chain of carbon atoms sequentially, starting at the end closest to the
substituent.
CH3 CH
CH2 CH2
CH3
CH3
1 2 3 4 5
methylpentane
The location and name of each substituent is followed by the root alkane name.
2-
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Example
3-methylhexaneCH3 CH
CH2 CH2
CH2
CH3
CH3
CH3 CH2 C CH2 CH3
H
CH3
3-methylpentane
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CH3 CH
CH2 CH2
CH2
3-methylhexaneCH3
CH3
Example
CH3 CH2 C CH2 CH3
H
CH3
3-methylpentane
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Alkane NomenclatureThe substituents are listed in alphabetical order, and
the prefixes di-, tri-, and so on are used to indicate multiple, identical substituents.
CH3 C CH2 CH2
CH3
CH3
CH3
2,2-Dimethylpentane
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Example
2,4-dimethylhexaneCH3 CH
CH2 CHCH2
CH3
CH3
CH CH2 CH2 C CH3
H
2-methylhexane
CH3
CH3
CH3
H
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Example
4-ethyl-3,5-dimethylheptane
CH2 CH CH CH
CH2
CH2
CH3
CH3
CH3CH3
CH3
CH2 CH2 CH2 C
CH2
CH2
CH3
CH3
CH3
CH2
CH3
3-ethyl-3-methyloctane
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Example
4-ethyl-3,5-dimethylheptane
CH2 CH CH CH
CH2
CH2
CH3
CH3
CH3CH3
CH3
CH2 CH2 CH2 C
CH2
CH2
CH3
CH3
CH3
CH2
CH3
3-ethyl-3-methyloctane
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CH3 CH
CH CH2
CH3
CH2
CH2
Alkane NomenclatureIf two chains of equal length are present, choose the one with the larger number of branch points as the
parent.
CH3
CH3
3-ethyl-2-methylhexane
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CH3 CH
CH CH2
CH3
CH2
CH2
Alkane NomenclatureIf two chains of equal length are present, choose the one with the larger number of branch points as the
parent.
CH3
CH3
3-isopropyl-hexaneNot
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The Chemistry of Alkanes
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Physical Properties of Alkanes
as molecular size increases so does the boiling point of the alkane
increased size increased dispersion forces
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Alkanes
CH4Methane
C2H6Ethane C
HH
HCH
HH
C3H8Propane
C4H10Butane
CH
HH
H
Boiling Point˚C
-161.6
-88.6
-42.1
-0.5(CH2)2 CH3CH3
(CH2)1 CH3CH3
C5H12Pentane 36.1(CH2)3 CH3CH3
C6H14hexane 68.7(CH2)4 CH3CH3
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Chemical Reactions and Alkanes
because the C-C and C-H bonds are relatively strong, the alkanes are fairly unreactive
their inertness makes them valuable as lubricating materials and as backbone material
in the construction of other hydrocarbons
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Combustion of Alkanes
these reactions are all highly exothermic
CH4 O2 CO2 2H2O+ +
C4H10 13/2O2 4CO2 5H2O+ +
ΔH˚-890.4 kJ
-3119 kJ
At high temperatures alkanes combust
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alkyl halide
An alkane in which one or more hydrogens have been replaced with halogens
CH3Cl
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Example
CH3 CH2 CH2 C CH3
H
Cl2-chloropentane
Br CH2 CH2 C CH3
H
Cl1-bromo-3-chlorobutane
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A Functional Groupa group of atoms that are largely responsible
for the chemical behavior of the parent molecule
NH2, F, Cl, Br, I, NO2 ,, ,some common
functional groups
Alkyl groups - derived from alkanes
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Elemental Composition
Empirical Formula
Molecular FormulaConstitution
Configuration
Conformation
Levels of Structure
√√√√
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Stereoisomersisomers that have the same constitution but differ in
the spatial arrangement of their atoms
CH3 CH
CH3
HCH
H CH3
H
H
CH3H
H
saw horse projection
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Stereoisomersisomers that have the same constitution but differ in
the spatial arrangement of their atoms
CH3 CH
CH3
HCH
H
saw horse projection
Conformations : different spatial arrangments of a molecule generated by rotation of atoms about single
bonds
CH3
H
HCH3
H
H
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Elemental Composition
Empirical Formula
Molecular FormulaConstitution
Configuration
Conformation
Levels of Structure
√√√√√
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EnantiomersStereoisomers that are related as an object and
its nonsuperimposable mirror image
ie: being chiral
C
Br
HF
Cl
bromochlorofluoromethane
C
Br
FH
Cl
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C
Br
HCl
F
mirror images
C
Br
ClH
F
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nonsuperimposable
C
Br
ClH
F
C
Br
HCl
F
amino acids are examples of molecules that have a chiral carbon
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Cycloalkanes
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Cycloalkanes
Alkanes whose carbon atoms are joined in rings
CnH2n
sp3 hybridization
C5H10cyclopentaneC
CC
C CH
HHH
HH
H
HH
H
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Alkane Nomenclaturefollows the same rules as for naming other alkanes except that the root name is preceded by the prefix
cyclo-
The ring is numbered to yield the smallest substitutent number possible.
CH3CH2
CH2CH2
CH2CH2
cyclobutane 1-ethylcyclobutane
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Example
1-Ethyl-2-methylcyclohexaneCH3
CH2 CH3
H3C
CH3
1,4-Dimethylcyclohexane
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Example
CH3
CH3
1,1-Dimethylcyclohexane
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Cyclohexane
CC
C C
H
HCHH
HH
H
H
HH C
HH
to attain tetrahedral bond angles the cyclohexane ring must “pucker”
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CyclohexaneTwo stable conformations C6H12
C
C C
C H
HC
H
H
HH
H
H
HH
C
H
H
Boat Thursday, April 2, 2009
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CyclohexaneTwo stable conformations C6H12
C
C C
C H
HC
H H
HH
H
H
HH C
H
H
Chair
Cyclohexane assumes the chair conformation 99%
of the time
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Fused Ring Cyclic Alkanes - Steroids
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Fused-Ring Cyclic Alkanes - Steroids
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Alkenes
multiple carbon-carbon double bonds result when hydrogen atoms
are removed from alkanes
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CnH2n
Alkenes
sp2 hybridization
hydrocarbons containing at least one carbon-carbon double bond
C2H4
Ethylene C C
H
H
H
HEthene
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these molecules are said to be unsaturated
unsaturated: more hydrogen can be added to the molecule
C2H4Ethene C CH
H
H
H
Alkenes
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Alkene Nomenclature
The location of the carbon-carbon double bond is indicated by the lowest numbered carbon atom
involved in the double bond.
The root hydocarbon ends in -ene rather than -ane.
1-ButeneCH3CH2 CH2CH2
CH3CH CHCH3 2-Butene
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Example
3-methyl-3-hexeneCH3 C CH CH2
CH2
CH3
CH3
CH3 CH2 C CH CH3
H
2-pentene
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Conformations of Alkenesrotation around the carbon-carbon double bond is
highly restricted but not impossible
the two H atoms are on the same side
the two H atoms are across from each other
C CH
CH3
H3C
HC C
H
CH3
H
H3C
cis-2-Butenetrans-2-Butene
thus alkenes exhibit cis-trans isomerism
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Conformations of Alkenes
less steric strain
C CH
CH3
H3C
HC C
H
CH3
H
H3C
cis-2-Butenetrans-2-Butene
thus alkenes exhibit cis-trans isomerism
rotation around the carbon-carbon double bond is highly restricted but not impossible
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Example
C CH
CH2CH3
H3C
H
C CH
CH2
H
CH2
cis-3-hexene
trans-2-pentene
CH3CH3
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Some Chemical Reactions involving Alkenes
addition reactions
with hydrogen halides
hydrogenation
with halogens
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Hydrogenation of ethylene
Exothermic ΔE˚ = -136 kJ/mol
catalyzed by finely divided Pt,Pd, Rh, Ni
CH
HC
H
HHH CH
HC
H
HH
H
+
Addition Reaction
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H HC
H
HC
H
H
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CH
HC
H
HH
H
H
H
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HH HC C
H
H
H
H
H
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HHC C
H
H
H
H
HH
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H H
HH HC C
HH
H
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Alkynes
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CnH n
Alkyneshydrocarbons containing at least one carbon-
carbon triple bond
sp hybridization
C2H2 C C HHEthyne
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Alkyne Nomenclature
alkynes involves the use of -yne as a suffix to replace the -ane of the parent molecule
number from the end closer to the carbon bearing the triple
1-ButyneCH3C CH2CHCH3C CCH3 2-Butyne
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Chemical Reactions and Ethyne (Acetylene)
Due to its high heat of combustion acetylene has many industrial uses
+ 5O2 4CO2 +CH )( HC 2H2O2
ΔH˚ -2599.2 kJ
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Aromatic Hydrocarbons
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Benzene
due to benzene’s high carbon to hydrogen ratio it was assumed that it would under go addition
reactions similar to that of alkenes and alkynes
C6H6
Benzene however proved to be relatively inert
Its formula was known relatively early on, but what as its structure???
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August Kekulededuced the
structure of benzene to be planar and
cyclicthe properties of benzene can be explained by delocalized
molecular orbitals
CCC C
HC
H
H
H
H CH
CCC C
HC
H
H
H
H CH
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Benzene C6H6
CCC C
HCH
H
H
H CH
The circle represents the electrons in the p system.
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H
H
H
H
H
H
Benzene C6H6
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H
H
H
H
H
H
Benzene C6H6
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NomenclatureNaming of monosubstituted benzene
CCC C
HCCl
H
H
H CH
CCC C
HCNO2
H
H
H CH
CCC C
HC
H
H
H CH
CH2 CH3
ethylbenzenechlorobenzenenitrobenzene
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NomenclatureIf more than one substituent is present we must indicate
the location of the second group relative to the first
CCC C
ClCCl
H
H
H CH
1,2-dichlorobenzene
CCC C
HCCl
Cl
H
H CH
1,3-dichlorobenzene
CCC C
HCCl
H
H
H CCl
1,4-dichlorobenzeneortho
metapara
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NomenclatureIf more than one substituent is present we must indicate
the location of the second group relative to the first
CCC C
ClCCl
H
H
H CH
CCC C
HCCl
Cl
H
H CH
CCC C
HCCl
H
H
H CCl
o-dichlorobenzenem-dichlorobenzene
p-dichlorobenzene
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Benzene C6H6
when benzene is used as a substituent, it is called the phenyl Group
CH3CCCH2
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NomenclatureAny group that contains one or more fused benzene
rings is called an aryl group
NaphthaleneAnthracene
phenathrene
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Graphite - fused aromatic rings in extended sheets held together with van der Waals forces
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CCC C
HC
H
H
H
H CH
CCC C
HHC
HH
HH
HH
HH C
HH
+ 3H2Pt
Chemical Reactions involving Aromatics
benzene can be hydrogenated with difficulty
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Polymerization
Building large molecules (polymers) from small molecules (monomers).
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CH2H2C CH2)(H2C
ethylene polyethylene
From http://www.chemheritage.org/EducationalServices/faces/poly/readings/rec.htm
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More Functional Groups
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Alcoholscontain at least one hydroxyl group (-OH)
CH
OHH
CH
HH
ethanol
CCC C
HC
OH
H
H
H CH
benzenolphenol
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AlcoholsThe systematic name for an alcohol is obtained by
replacing the -e of the parent hydrocarbon with -ol.
The -OH group is specified by a number
OHCH
HH
CH
HCH
HCH
H
CH
CH
HH
CH
OHHH
2-butanol
1-propanol
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Ethers
Diethyl ether
CH
HH
O CH
HCH
HH
CH
H
contain the ( R O R ) group
Ethyl methyl ether
CH
HH
OCH
HH
CH
H`
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Ethers
Ethyl methyl ether
CH
HH
OCH
HH
CH
H
Diethyl ether
CH
HH
O CH
HCH
HH
CH
H
Names of ethers are derived by listing the two alkyl groups in the general structure ROR’ in alphabetical order as separate words, and then adding ether to the
end.
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Aldehydes and Ketones
(formaldehyde)
contain a carbonyl group
Aldehydesat least one hydrogen is bonded
to the carbonyl group C
O
H H
2-butanoneKetones
no hydrogen atoms bonded to the carbonyl group
C
O
CH2CH3H3C
C O
methanal
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Carboxylic Acidscontain a carboxyl group C
O
OHR
Acetic acid C
O
OHH3C
C
O
OHHFormic acid
CCC C
HC
H
H
H CH
C
O
OH
Benzoic acid(used in FP Depression lab we did)
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EstersHave the general formula R COOR
C
O
OR RC
O
O
Ethyl acetate
CH2CH3CH3
Ethyl benzoate
C
O
O CH2CH2
C
O
O
Methyl propanoate
CH3CH3CH2
`
`
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Aminescontain at least one amine group (-NH2)
CH
NH2
HCH
HH
ethylamine
butylamine
CH3CHCH2CH2 NH2
CCC C
HC
NH2
NH2
H
H CH
1,3-benzenediamine
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Amino Acids
polymerize to form peptides (a few amino acids long) and proteins (hundreds of amino acids long)
+
+ ???1 2
+ H2O
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