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Organic Chemistry
Introduction
Functional Groups
AlkanesAlkenes
Alkynes
AlcoholsAcids, Esters and
Amides
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Introduction
Organic chemistry is the study of carbon-
containing compounds
especially compounds containing C-C
bonds The field of organic chemistry is very important
for a wide variety of reasons.
A huge number of carbon-containing
compounds are known.More than 16 million known compounds
About 90% of new compounds made each
year contain carbon
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Introduction
Most of the advances in the pharmaceutical
industry are based on a knowledge of
organic chemistry.
Many drugs are organic compounds Life as we know it is based on organic
chemistry.
Most biologically important compounds
contain carbon:DNA, RNA
proteins
carbohydrates
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Introduction
Learning organic chemistry requires you to
integrate and apply many of the concepts
you¶ve learned in general chemistry:
Electron configuration
Valence bond theory
Lewis structures
Resonance structuresHybrid orbitals
Molecular geometry
Acid/base reactions
Oxidation/reduction
Kinetics
EquilibriumThermodynamics
Stoichiometry
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Introduction
Some familiar organic compounds:
H
C
C C O
H
H
H
O
H
H
H
H
H
C
C C O
H
H
H
O
H
H
H C C
H H
H
H H
H
H O
C C HH C C C H
H
H
O H
H
methane
acetylene
acetone
propane
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Introduction
Some familiar organic compounds:
H C C O H
H
H
H H
H
C C
H
H H
H C C O
H
H
H
H
H
H C C O
H
H
H
O
C
O C
OOH
CH3
O
Acetic acid
Ethyl alcohol
³ether´
aspirin
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Introduction
Most organic compounds have a ³skeleton´
that is composed of C-C bonds.
The C-C bonds may be single bonds,
double bonds, or triple bonds.
The ³skeleton´ of an organic compound has
H¶s attached to it.
other ³heteroatoms´ like O, halogens or Nmay be present as well
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Introduction
The number of bonds formed by C in an
organic compound is determined by the
electron configuration of C.
Carbon has four valence electrons:
1s22s22p2
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Introduction
Carbon generally forms 4 equivalent bonds.
The formation of four equivalent bonds is
best explained using the concept of hybrid
orbitals.
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Introduction
The structure of an organic compound can
be predicted by drawing a Lewis structure:
H O H
H C C C H
H H
acetone
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Introduction
In organic molecules, we generally describe
the geometry around each carbon atom.
Geometry is predicted using:
VSEPR
hybrid orbitals
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Introduction
When C forms four single bonds:
sp3 hybrid orbitals are involved
tetrahedral geometry
When C forms a double bond:
sp2 hybrid orbitals are used
trigonal planar geometry
When C forms a triple bond:
sp hybrid orbitals are used
linear geometry
C CH
H
H
H
H C C H
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Introduction
Example: Identify the electron domain
geometry and hybrid orbitals used by each
atom (except hydrogen) in the following
compound.
C CH C C O H
OH
H
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Introduction
Organic compounds contain not only C-Cbonds but also C-H bonds.
C-C and C-H bonds tend to be non-polar
because there is a small difference in
electronegativites
Most (but not all) organic compounds are
relatively non-polar
generally not very soluble in water
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Hydrocarbons
The simplest organic compounds are thehydrocarbons:
organic compounds that contain only
carbon and hydrogen
four general types:
alkanes
alkenes
alkynes
aromatic hydrocarbons
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Hydrocarbons
Alkanes:hydrocarbons that contain only single
bonds
Examples:
Methane CH4
ethane H H
H ± C ± C ± H
H H
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Hydrocarbons
Alkenes:hydrocarbons that contain a C = C double
bond
H2C = CH2 (ethylene)
Alkynes:
hydrocarbons that contain a C C triple
bond
H ± C C ± H (acetylene)
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Hydrocarbons
Aromatic hydrocarbons:contain a planar ring structure in which
the carbon atoms are connected by a
combination of both W and T bonds
HH
CC
CC -- HH
CC -- HHHH -- CC
HH -- CC
CC
HH
benzene
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Introduction
Organic compounds that are soluble in polar solvents such as water generally have a
polar functional group present in the
molecule.
An atom or group of atoms that influences
the way the molecule functions, reacts or
behaves.
an atom or group of atoms in a molecule
that undergoes predictable chemical
reactions
the center of reactivity in an organic
molecule
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Introduction
Functional groups that contain O or N atomsoften lead to a polar organic molecule
large difference in electronegativity
C vs. O
C vs. N
Examples of familiar polar organic
compounds:
glucose
acetic acid
Vitamin C
amino acids
Functional groupscontain C-O bonds
Functional groups contain
C-O and C-N bonds
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Functional Groups
Since functional groups are responsible for the many of the chemical and physicalproperties of organic compounds, we oftenclassify and study organic compounds by
the type of functional group present.
On your exam, you will be responsible for recognizing and naming the variouscommon functional groups that are found inorganic compounds:
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Functional Groups
FunctionalGroup
p of Co poun a pl
C C al n H2C CH2
C C al n HC CH
C H alco ol CH3OH
C O C et er CH3CH2OCH2CH3
C a ine CH3NHCH3
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Functional Groups
FunctionalGroup
Type of Compound Example
O
C ± H aldehyde
O
CH3C ± H
O
C ± C ± C ketone
O
CH3 ± C ± CH3
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Functional Groups
FunctionalGroup
Type of Compound Example
O
C ± O ± HCarboxylic
acid
O
CH3C ± O ± H
O
C ± O ± C ester
O
CH3C ± O ± CH2CH3
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Functional Groups
FunctionalGroup
Type of Compound Example
O
C ± N ± amide
O
CH3C ± N ± CH3
H
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Functional Groups
Example: Name the functional group(s) that is(are) present in the following compounds:
H2C CH2
H2C CH2
CH3NHCH2CH2OCH3
OO
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Hydrocarbons
Alkanes are often called saturatedhydrocarbons
they contain the largest possible number
of hydrogen atoms per carbon atom.
Alkenes, alkynes, and aromatic
hydrocarbons are called unsaturated
hydrocarbons
they contain less hydrogen than an alkane
having the same number of carbon atoms
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Alkanes
Some of the simplest alkanes:
Con enseorm la Name
CH4 methane
CH3CH3 ethane
CH3CH2CH3 propane
CH3CH2CH2CH3 butane
CH3CH2CH2CH2CH3 pentane
You
mu
st know these!!!You
mu
st know these!!!
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Alkanes
Some of the simplest alkanes:
CondensedFormula Name
CH3CH2CH2CH2CH2CH3 hexane
CH3CH2CH2CH2CH2CH2CH3 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane
You must know these!!!You must know these!!!
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Alkanes
The previous alkanes are also calledstraight-chain hydrocarbons:
all of the carbon atoms are joined in a
continuous chain
Alkanes containing 4 or more carbons can
also form branched-chain hydrocarbons
(branched hydrocarbons)
some of the carbon atoms form a ³branch´
or side-chain off of the main chain
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Alkanes
An example of a straight chain hydrocarbon:
C5H12 CH3CH2CH2CH2CH3 pentane
Examples of a branched hydrocarbon:
C5H12 CH3CHCH2CH3 CH3
CH3 CH3CCH3
CH3
2-methylbutane
2,2-dimethylpropane
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Alkanes
The three structures shown previously for C5H12 are structural isomers:
compounds with the same molecular
formula but different bonding
arrangements
Structural isomers generally have different
properties:
different melting points
different boiling points
often different chemical reactivity
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Alkanes
Alkanes with three or more carbons can alsoform rings or cycles.
Cycloalkanes:
Alkanes containing a ring structure that isheld together by C ± C single bonds
Examples: CHCH22
CHCH22HH22CC
cyclopropanecyclopropane
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Alkanes
Examples of cycloalkanes:
CHCH22
CHCH22
CHCH22HH22CC
HH22CC cyclopentanecyclopentane
HH22CC
HH22CC CHCH22
CHCH22
CHCH22
CHCH22
cyclohexanecyclohexane
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Alkanes
Organic compounds can be named either using common names or IUPAC names.
You must be able to name alkanes, alkenes,
alkynes, and alcohols with 10 or fewer carbons in the main chain using the IUPAC
naming system.
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Alkanes
Alkane Nomenclature:Find the longest continuous chain of
carbon atoms and use the name of the
chain for the base name of the compound:
longest chain may not always be writtenin a straight line
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
1 2
34 5 6
Base name:Base name:
hexanehexane
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Alkanes
Alkane Nomenclature:Number the carbon atoms in the longest
chain beginning with the end of the chain
closest to a substituent
groups attached to the main chain thathave taken the place of a hydrogen
atom on the main chain
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
11 22
3344 55 66
A substituentA substituent
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Alkanes
Alkane Nomenclature:Name and give the location of each
substituent group
A substituent group that is formed by
removing an H atom from an alkane iscalled an alkyl group:
Name alkyl groups by dropping the ³ane´
ending of the parent alkane and adding³yl´
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Alkanes
Alkane Nomenclature:Common alkyl groups (substituents):
CH3 methyl
CH3CH2 ethylCH3CH2CH2 propyl
CH3CH2CH2CH2 butyl
22--methylhexanemethylhexaneCH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
11 22
3344 55 66
KnowKnowthese!these!
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Alkanes
Alkane Nomenclature:
Halogen atoms are another common class
of substituents.
Name halogen substituents as ³halo´:Cl chloro
Br bromo
I iodo
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Alkanes
Alkane Nomenclature:When two or more substituents are
present, list them in alphabetical order:Butyl vs. ethyl vs. methyl vs. propyl
When more than one of the samesubstituent is present (i.e. two methylgroups), use prefixes to indicate thenumber:Di = two Tri = three Tetra = four Penta = five
Know these.Know these.
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Alkanes
Example: Name the following compounds:
CH3CH2CHCH2CH3
CH3
CH2CH2CH3
CH3CHCHCH3
CH3
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Alkanes
Example: Name the following compounds:
CH3CH2CHCH3
CH2CH2Br
CH2CH2CH3
CH3CHCHCH3
Cl
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Alkanes
You must also be able to write the structureof an alkane when given the IUPAC name.
To do so:
Identify the main chain and draw thecarbons in it
Identify the substituents (type and #) and
attach them to the appropriate carbon
atoms on the main chain.Add hydrogen atoms to the carbons to
make a total of 4 bonds to each carbon
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Alkanes
Example: Write the condensed structure for the following compounds:
3, 3-dimethylpentane
3-ethyl-2-methylhexane
2-methyl-4-propyloctane
1, 2-dichloro-3-methylheptane
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Alkenes
Alkenes:unsaturated hydrocarbons that contain a
C=C double bond
Alkene Nomenclature:Names of alkenes are based on the
longest continuous chain of carbon atoms
that contains the double bond.
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Alkenes
Alkene NomenclatureFind the longest continuous carbon chain
containing the double bond.
Change the ³ane´ ending from thecorresponding alkane to ³ene´
butane butene
propane propene
octane octene
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Alkenes
Alkene NomenclatureIndicate the location of the double bond
using a prefix number
designate the carbon atom that is part
of the double bond AND nearest to theend of the chain
Name all other substituents in a manner
similar to the alkanes.
Use a prefix to indicate the geometric
isomer present, if necessary.
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Alkenes
Alkene Nomenclature
Different geometric isomers are possible for
many alkenes.
Compounds that have the same molecular formula and the same groups bonded to
each other, but different spatial
arrangements of the groups
cis isomer
trans isomer
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Alkenes
Alkene NomenclatureCis isomer:
two identical groups (on adjacent
carbons) on the same side of the C = C
double bond
Trans isomer:
two identical groups (on adjacent
carbons) on opposite sides of the C = Cdouble bond
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Alkene
cis-2-butene
CHCH33 CHCH33
C = CC = C
HH HH
CHCH33 HH
C = CC = C
HH CHCH33
trans-2-butene
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Alkene
For an alkene with the general formulaFor an alkene with the general formula
AA PP
C = CC = C
BB QQ
cis and trans isomers are possible only if cis and trans isomers are possible only if
A = B andA = B and
P = QP = Q
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Alkene
Example: Name the following alkenes:
CH3CH2 H
C = C
H H
CH3CH2 H
C = C
CH3CHCH2 CH2CH3
CH3
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Alkenes
Example: Draw the structures for the followingcompounds:
2-chloro-3-methyl-2-butene
trans-3, 4-dimethyl-2-pentene
cis-6-methyl-3-heptene
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Alkynes
Alkynes:unsaturated hydrocarbons that contain a
C C triple bond
Alkyne Nomenclature:Identify the longest continuous chain
containing the triple bond
To find the base name, change the endingof the corresponding alkane from ³ane´ to
³yne´
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Alkynes
Alkyne Nomenclature:Use a number to designate the position of
the triple bond
number from the end of the chain
closest to the triple bondjust like with alkenes
Name substituents like you do with
alkanes and alkenes
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Alkynes
Example: Name the following compounds:
CH3CH2C CCHCH3
CH2CH3
CH2CH2C CH
Cl
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Alkynes
Example: Draw the following alkynes.
4-chloro-2-pentyne
3-propyl-1-hexyne