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Organic Chemistry
Muh. Yanis Musdja
The Study of the
Compounds of Carbon
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Carbons Place on the
Periodic Table
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Why does Carbon form so
many interesting compounds?
Easily forms bonds with other C atoms.
Forms double and triple bonds with other C atoms.
Can form long chains (and rings) of C-C bonds.
Ubiquitous/Found everywhere.
Depending on bonding (presence of single, double,or triple bonds) carbon compounds can exhibittetrahedral, trigonal planar or linear geometries
Though carbon and hydrogen form the backbonestructure, carbon can also bond to other elements,like O and N, which are called heteroatoms
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Carbon Skeletons
Since carbon bonds four times, it can assumea very complex set of bonding arrangements.
Single bonded carbons can rotate relative to
one another, so arrangements can be
represented in different ways, as shown
below:
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H
H
H
A C atom single-bonded
to one other atom gets
three H atoms.
C C
A C atom single-bonded
to two other atoms gets
two H atoms.
C C C
H
H
A C atom single-bonded
to three other atoms gets
one H atom.
C C C
C
H
A C atom single-bonded
to four other atom is
already fully bonded (no
H atoms).
C C C
C
C H
H
A double- and single-
bonded C atom or a
triple-bonded C atom is
treated as if it were
bonded to three other
atoms.
CC C
C C
H
H
A double-bonded C atom
is treated as if it were
bonded to two other
atoms.
CC
Hydrogen Skins
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Hydrocarbon Representations
C C H
H
H
C
H
HH
H
C
H
H
C
H
H
C
H
H
H Expanded Structure
CH3CH2CH2CH2CH2CH3 Condensed Structure
Bond-line Representation
C6H14 Molecular Formula
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IsomersNote that for the formula C6H14, several possible structures
exist. These alternate forms are called structural isomers.
Note that each of these isomers is a different compound
with different properties - and a different name.
CH3CH2CH2CH2CH2CH3
CH3CHCH2CH2CH3
CH3
CH3CH2CHCH2CH3
CH3
CH3CHCHCH3
CH3
CH3
One more isomer exists. Can you suggest what it is?
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Functional Groups
Groups of atoms bonded in a particular way. They tend to
act as a unit and react in a similarway despite the rest
of the compound.
Many functional groups contain electronegative elements
(N,O) and contain polar bonds.
Incomplete list of Functional groups:
1. -C=C- alkene
2. -CC- alkyne
3. -C-OH alcohol
4. -C-O-C- ether
5. -C-NH2 amine
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Most basic organic compounds: hydrocarbons
Hydrocarbons contain only the elements C and H. They
are all non-polar. They are classified by the types ofC/C bonds they contain:
1. C-C single bonds only alkanes
2. C=C double bonds alkenes
3. CC triple bonds alkynes
4. Alternating double and single aromatic
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Examples
Alkane: CH3CH2CH2CH2CH3
Alkene: CH2=CHCH2CH2CH3 or
Alkyne: CHC-CH2CH2CH3 or
Aromatic:
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Hydrocarbon Nomenclature
Number of
C atomsRoots
1
2
3
4
5
6
8
7
9
meth-
eth-
prop-
but-
hex-
pent-
hept-
oct-
non-
dec-
PREFIX + ROOT + SUFFIX
10
Note that
beginning
with 5 Cs,
the roots are
numerical
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Rules for Naming AlkanesNote that alkanes contain only single bonds and have the
generalized formula CnH2n+2
Rules for Naming Organic Compounds
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Alkane Nomenclature Examples
Suggest appropriate names for the following:
CH3CHCH2CH2CH3
CH3
CH3CHCHCH2CH3
Br
CH3
CH3CHCH2CHCHCH3
CH3
CH3
Cl
CH3CH2CHCHCH2CHCH3
CH2CH3
Br
CH3
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Alkane Nomenclature Examples (II)
Suggest appropriate names for the following:
CH3CHCH2CH2CH3
CH3
CH3CHCHCH2CH3
Br
CH3
CH3CHCH2CHCHCH3
CH3
CH3
Cl
CH3CH2CHCHCH2CHCH3
CH2CH3
Br
CH3
2-methylpentane
2-bromo-3-methylpentane
4-chloro-2,5-dimethylhexane 4-bromo-5-ethyl-2-methylheptane
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Alkane Nomenclature (III)
Suggest reasonable structures for the following names:
5-bromo-2,2-dimethyloctane 3-ethyl-2,3,4-trimethylhexane
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Alkane Nomenclature (IV)
Suggest reasonable structures for the following names:
5-bromo-2,2-dimethyloctane 4-ethyl-2,3,5-trimethylheptane
CH3CCH2CH2CHCH2CH2CH3
CH3
CH3
Br
CH3 CH CH CHCH CH2 CH3
CH3
CH3
CH2H3
CH3
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Cycloalkane Representations
C
C C
H H
H
HH
H
C
C C
CH
H
H
H
H
H H
H
cyclopropane cyclobutane
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Cycloalkanes
Cycloalkanes contain rings, and have the generalized
formula: CnH2n Cycloalkanes are usually representedby polygons, as shown below:
Cyclopropane Cyclobutane
Cyclopentane Cyclohexane
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Cycloalkane NomenclatureWhen only one substituent is on the ring, numbering is not necessary.
Chlorocyclohexane
When two or more substituents are present, the substituent that is first
alphabetically is assumed to be on carbon one, and the others are
numbered, clockwise or counter-clockwise to give the smallest number
arrangement.
1-chloro-3-methylcyclopentane
ClCl
Cl
CH3CH3
Cl
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Alkenes Alkenes contain at least one double bond.
Their molecular formula is CnH2n
The double-bonded carbons have trigonal planar
geometries.
An expanded structure for ethene, the simplest alkene,is shown below:
C C
H
H116.6o
H
H121.7o
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Alkenes (II)Note that there is no rotation around a double bond, in
contrast to single bonds. This factor leads to thepossibility ofcis-trans, or geometric, isomerism. When
atoms are bonded to double-bonded carbons, they are
constrained to remain in the same position. For
example, two kinds of 2-butene exist as is shown below:
C CCH3
H
CH3
H
C CH
CH3
CH3
Hcis-2-butene trans-2-butene
CH3 groups are cis, or
same side of double bond
CH3 groups are trans, or
opposite one another
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Alkene Nomenclature
The double bond plays a prominent rolein alkene nomenclature. Despite
whatever else is present, the carbon
chain is numbered from whichever endis closest to the double bond.
When a double bond is present, the
name ending is changed from -ane to-ene.
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Alkene Nomenclature (II)
Example 1:
C CCH2CH3
H
CH3
H
This compound is called 2-pentene, or more correctly,
c is-2-pentene, since the continuing carbon chains are
situated on the same side of the double bond.
Generally, if sufficient structure information is provided,
you should assign a cis or trans designation to the name
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Alkene Nomenclature (III)
Other rules we have learned also apply to alkenes, except
that the double bond dictates the direction of chain
numbering. For example:
C CH
CH2CHCH3
CH3
CH2
H
trans-6-bromo-3-heptene
Br
Note that the double bond determines chain
numbering, not the bromo group.
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Alkene Nomenclature (IV)
Provide a complete, correct name for the following:
C CH
CH2CCH3CH3
H
Br
CH3
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Alkene Nomenclature (IV)
Provide a complete, correct name for the following:
C CH
CH2CCH3CH3
H
Br
CH3
cis-5-bromo-5-methyl-2-hexene
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CycloalkenesCycloalkenes, which have a molecular formula of C
n
H2n-2
,
share many characteristics of alkenes, however, in order to
form rings, the double bond generally must be in the cis form.
When naming a cycloalkene, it is understood that the double-
bonded carbons are numbered 1 and 2. Examples:
Cyclohexene
3-
methylcyclohexeneCH
3CH3
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Alkynes
Hydrocarbons containing a triple bond are
called alkynes, and have molecular
formulas of CnH2n-2.
The triple bonded carbons exhibit linear
geometries, with bond angles of 180o.
This geometry prevents them from
forming rings.
Nomenclature for alkynes is completely
analogous to the method for alkenes.
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Aromatic Hydrocarbons
Aromatic hydrocarbons are ring structures
with multiple double bonds. The doublebonds are conjugated, alternating doubleand single bonds.
Aromatic hydrocarbons have molecularformulas approaching CnHn.
These structures are planar, with all ringcarbons exhibiting a trigonal planargeometry, and a high degree of resonance.
A number of aromatics are notoriouscarcinogens
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Aromatic Nomenclature
NH2 CH3 OHOH
Benzene Aniline Toluene Phenol
NH2 CH3 OHOH
Benzoic
Acid
COOH
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Aromatic Nomenclature (II)
Nomenclature for aromatics is performed much like othercyclic compounds.
If only one substituent is present, numbering is unnecessary
If one of the common names, such as phenol, is used, it is
understood that the substituent is on carbon 1. Othersubstituents present are numbered or given a special
designation used in aromatic chemistry.
In general, substituents are numbered by counting
clockwise or counterclockwise to produce the lowest
numbering pattern.
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Aromatic Nomenclature (II)
Nomenclature for aromatics is performed much like
other cyclic compounds.
If only one substituent is present, numbering isunnecessary
If one of the common names, such as phenol, is used, it
is understood that the substituent is on carbon 1. Othersubstituents present are either numbered or given aspecial designation used in aromatic chemistry.
1-2 substitution is called ortho
1-3 substitution is called meta
1-4 substitution is called para
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Aromatic Nomenclature (III)
Examples:
3-chloroaniline
ormeta-chloroaniline
4-bromotoluene
orpara-bromotoluene
2,4-dimethylphenol
NH2
Cl
NH2
Cl
CH3
Br
CH3
Br
OH
CH3
CH3
CH3
CH3
OH
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Hydrocarbon Chemistry
Hydrocarbons are generally derived
from natural sources, particularlypetroleum.
The most plentiful compounds in
petroleum are alkanes. A number of reactions can be used to
convert one type of hydrocarbon intoanother.
Organic compounds are much morereactive when heteroatoms, N and O,are present.
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Alkanes
Alkanes are generally considered to beunreactive.
They are commonly combusted as
gasoline, diesel, kerosene, etc. They can also be reacted with the
halogens, e.g. Cl2 and Br2, to form
halogenated forms. The halogenated forms can be used to
produce other compounds.
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Alkenes
The double bond in alkenes makes them much
more reactive than alkanes.
The pi electrons in the double bond are relatively
loosely held, and the double bond is subject to
attack by substances attracted to negative charge(electrophiles).
Generally, substances are added to the doubly
bonded carbons, and the double bond is lost.
Ethylene and propylene are heavily used toproduce polymers polyethylene and
polypropylene.
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Alkynes
Alkynes have two pi bonds, and reactmuch like alkenes, except that
stoichiometrically they tend to react twice
as much.
The most common alkyne, acetylene, is
capable of participating in unusual
reactions with strong bases, and it
combusts at very high temperature, whichmakes it ideal for welding torches.
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Aromatic Compounds
Although aromatic compounds containdouble bonds, they do not react likealkenes, because the loss of double bondswould eliminate their stabilizing resonance.
Instead, aromatic compounds tend toundergo substitution reactions, where othersubstances replace hydrogen atoms on thering carbons.
A number of aromatic hydrocarbons areproduced as pollutants when otherhydrocarbons are burned.
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Alcohols
When a carbon atom is bonded to an -O-Hgroup, often designated as R-O-H, where Ris used as a general designation for a carbongroup, the molecule is called an alcohol.
The -OH group is very polar, and most smallalcohols have high boiling points and goodwater solubility.
Besides simple alcohols, alcohols are foundbiologically in carbohydrates and variousmetabolites.
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Alcohol Nomenclature
Alcohols often have common trivial names,
but IUPAC nomenclature rules suggest that
the alcohol name contain the -ol suffix.
The alcohol group is considered higher
priority than any carbon-containing group,and the chain should be numbered from
whichever end is closest to the alcohol
group. Other groups are named and numbered as
shown previously
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Alcohol Nomenclature (II)
Examples:
CH3CH2-OHEthyl alcohol (trivial name)
Ethanol (IUPAC name)
CH3CHCH2CHCH3
Cl OH
4-chloro-2-pentanol
CH3
OH
CH2CH2CHCH2CHCH3
CH3Br OH6-bromo-4-methyl-2-hexanol
3-methylcyclohexanol
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Ethers
Another oxygen-containing functional group
is the ether. The ether group, sometimesdesignated as R1-O-R2, contains an oxygenbridge between two carbon atoms.
Ethers, unlike alcohols, do not participate inhydrogen bonds, and are not consideredpolar.
Ethers, which are important medical andindustrial chemicals, are not commonlyfound naturally in biological systems.
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Ether Nomenclature
Although IUPAC recommends a methodfor naming ethers, we will only focus on
a trivial method that is in common use.
With this method, the two carbon-containing groups connected by the
oxygen are listed alphabetically,
followed by the name ether.
( )
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Ether Nomenclature (II)
Examples:
CH3-O-CH2CH3 Ethyl methyl ether
CH3CH2-O-CH2CH3 Diethyl ether
O
CH3 Cyclohexyl methyl ether
Diethyl ether was used for years as an anesthetic until it
was replaced due to safety considerations.
C b l G
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Carbonyl Groups
The carbonyl group contains a carbon-
oxygen double bond. This functional group
can be found in the interior of a carbon
chain, where it is called a ketone, or on a
terminal carbon, where it called an aldehyde.
A commonly used representations of
ketones and aldehydes look as follows:
R1-C-R2
O||
R-C-H or RCHO
O||
Ketone Aldehyde
C b l G (II)
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Carbonyl Groups (II)
Carbonyl groups, particularly aldehydes, are veryreactive, and appear in many biologicalcompounds.
Like alcohols, carbonyl groups are found incarbohydrates, and they are observed duringmany metabolic processes
These compounds are moderately polar, and thesmaller ketones and aldehydes are water soluble.
A number of ketones have common names, suchas acetone and methyl ethyl ketone (MEK), andare widely used industrial solvents.
K t N l t
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Ketone Nomenclature
When a ketone is present in a compound, it
is considered higher priority than anything
discussed thus far, and the chain is
numbered from whichever end is closest to
the ketone. If an alcohol is also present, itis given a number and is called a hydroxy
group.
When a ketone is present, the suffix for thename is changed to -one.
K t N l t (II)
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Ketone Nomenclature (II)
Examples:
Acetone (trivial name)
2-propanone (IUPAC name)
CH3CCH2CH3
O||
CH3CCH3
O||
Methyl ethyl ketone (trivial name)
2-butanone (IUPAC name)
CH3CHCCH2CHCH3
O||
OH|
CH3|
5-hydroxy-2-methyl-3-hexanone
Ald h d N l t
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Aldehyde Nomenclature When an aldehyde is present in a compound, it is
considered higher priority than anything discussedthus far, and the chain is numbered from aldehyde
end. The aldhyde group is understood to be on the
terminal carbon, so it needs no number. If ketones
are also present, they are called oxo groups andare given a number.
When an aldehyde is present, the suffix of the name
is changed to -al. Remember, aldehydes can be represented as:
R-C-H or RCHO
O||
Ald h d N l t (II)
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Aldehyde Nomenclature (II)Examples:
CH3C-H
O|| Formaldehyde (trivial name)
Methanal (IUPAC name)
CH3CCH2CHO
O||3-oxobutanal
CH3CHCCH2CHCHO
O||
OH|
Cl|
5-chloro-2-hydroxy-4-oxohexanal
C b li A id
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Carboxylic Acids Carboxylic acids have the generalized formula:
The carboxyl name is a contraction of carbonyland hydroxyl group names, which are bothpresent.
The hydrogen on the hydroxyl group is acidic, andcarboxylic acids are notable for their acidicbehavior.
Carboxylic acids are found in many biologicalcompounds, most notably amino acids.
R-C-OH or RCOOH
O||
C b li A id N l t
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Carboxylic Acid Nomenclature
The carboxylic acid structure requires that this
functional group be on a terminal carbon. The carboxyl group has higher priority than
any other functional group, and if it is present,
it is understood to be on carbon number 1,and the chain is numbered away from it.
Other groups present are numberedappropriately, and the names suffix is
changed to -oic, followed by the word acid.
There are many trivial names, such as aceticacid that are commonly used.
C b li A id N l t (II)
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Carboxylic Acid Nomenclature (II)Examples:
CH3C-OH
O||
Acetic acid (trivial name)
Ethanoic acid (IUPAC name)
CH2CH2CH2COOH
OH|
Gamma-hydroxybutyric acid or GHB(trivial name)
4-hydroxybutanoic acid
CH3CHCCH2CHCOOH
Cl|
CH3|
Cl|
4,5-dichloro-2-methylhexanoic acid
A i
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Amines
Amines act as bases in organic chemistry. They contain the amino functional group:
R-NH2
These compounds are notable for theirbasic nature and strong odors.
Nitrogen-containing compounds, or amines,are found in a variety of biological
compounds including amino acids andnucleic acids.
A i N l t
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Amine Nomenclature
Amines are commonly named by referring to the alkyl
group attached to them, followed by the word amine.
In IUPAC, or systematic, nomenclature, the amine is
numbered from which ever end of the chain is closest.
The final e of the name is replaced by the suffix -amine. If a higher priority group is present, the amine is called an
amino group and given a number. All of the oxygen-
containing functional groups are considered higher priority.
Finally, though we wont cover them, amines exist wheremore than one carbon group is attached to the nitrogen
atom.
A i N l t (II)
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Amine Nomenclature (II)
Examples:
CH3CHCH3
NH2|
Isopropyl amine (trivial name)
2-propanamine (IUPAC name)
CH3CHCH2CH2-OH
NH2|
3-amino-1-butanol
CH3CHCOOH
NH2|
Alanine (amino acid)
2-aminopropanoic acid