Download CH 3

ORGANIC FUNCTIONAL
GROUPS AND NOMENCLATURE
ALKYL GROUPS
• An alkyl group is an unbranched alkane
with a hydrogen atom removed from
the terminal, or end, carbon.
• To name the alkyl group, replace the –
ane ending of the unbranched alkane
with –yl.
• Thus, if you take one hydrogen from
CH4, it becomes —CH3, and the name
changes from methane to methyl.
NAMES OF ALKANES and ALKYL GROUPS
Alkane
Molecular
Formula
Structural
Formula
Alkyl
Molecular
Formula
Methane
CH4
CH4
Methyl
CH3
Ethane
C 2H 6
CH3CH3
Ethyl
C 2H 5
Propane
C 3H 8
CH3CH2CH3
Propyl
C 3H 7
Butane
C4H10
CH3(CH2)2CH3
Butyl
C4H 9
Pentane
C5H12
CH3(CH2)3CH3
Pentyl
C5H11
Hexane
C6H14
CH3(CH2)4CH3
Hexyl
C6H13
Heptane
C7H16
CH3(CH2)5CH3
Heptyl
C7H15
Oktane
C8H18
CH3(CH2)6CH3
Oktyl
C8H17
Nonane
C9H20
CH3(CH2)7CH3
Nonyl
C9H19
Dekane
C10H22
CH3(CH2)8CH3
Dekyl
C10H21
Undekane
C11H24
CH3(CH2)9CH3
Undekyl
C11H23
Dodekane
C12H26
CH3(CH2)10CH3
Dodekyl
C12H25
ALKYL GROUPS ANIMATION
•
• Carbon atoms are classified as primary, secondary, tertiary, or
quaternary based on the number of non-hyrogen groups attached to
the sp3 carbon.
• The hydrogen atoms attached to these carbon atoms are given the
same designation.
Primary,secondary and tertiary
carbon atoms
• Organic compounds often
contain functional groups
bonded on to different types
of carbon chains.
• These can often be usefully
distinguished using the terms
primary,secondary and
tertiary.
• Primary means that the
carbonthat the functional
group is joined to is bonded to
only one other carbon atom
• Secondary means that it is
bondedto two other carbon
atoms
• Tertiary three other carbon
atoms.
METYL,ETHYL and PROPYL GROUPS
methyl
H
|
H-C|
H
ethyl
H H
| |
H-C-C| |
H H
n-propyl
or simply
propyl
H H H
| | |
H-C-C-C| | |
H H H
isopropyl
H H H
| | |
H-C-C-C-H
| | |
H
H
DRAWING PROPYL GROUPS IN A VARIETY
OF ORIENTATIONS
 The skeletal structural formulas shown




here are intended to emphasize the fact
that the n-propyl and isopropyl groups
can be drawn in a variety of orientations.
It is not the way that the Cs are drawn
that makes the difference.
It is the location of the bond to
something else that distinguishes npropyl from isopropyl.
Starting from the bonding point in a
normal propyl group there is a
continuous string of three carbon atoms.
Starting from the bond point in an
isopropyl group the three carbon atoms
are not continuous, instead they are
branched.
n-propyl
isopropyl
BUTYL GROUPS
The next set of alkyl groups contains four carbons. That is why they are called
butyl groups. There are four types of butyl groups each with a different
combination of carbon chain and bonding point.
The first one is a straight chain with an
H missing from the end and is called a
normal butyl group (or n-butyl group).
The next one is iso-butyl (usually
spelled isobutyl). It has a branched
chain at the end opposite where it
attaches to something else.
There is also a secondary-butyl which
is often referred to as sec-butyl. Its
structural arrangement is shown here.
Also, tertiary-butyl (also called tertbutyl or t-butyl) has a fourth kind of
arrangement as shown.
n-butyl
or
butyl
iso-butyl
or
isobutyl
sec-butyl
tert-butyl
or
t-butyl
TRIVIAL(COMMON) AND IUPAC NAMES OF
COMMON ALKYL GROUPS
PENTYL GROUPS
There are eight different pentyl groups (-C5H11), but only
four of these have trivial names. These four are shown
above.
ALKYL GROUP
• Note that an alkyl group (CnH2n+1, like an
alkane with one H removed) can be
represented by R.
• Thus alcohols (which contain the
hydroxyl group — OH) can be
represented as ROH.
• Similarly the benzene ring can be
represented as so that phenol (a
benzene ring with an — OH attached) is
represented as
ALKENYL GROUP
• An alkenyl group is a hydrocarbon
group formed when a hydrogen atom is
removed from an alkene group.
• Alkenyl compounds are named by
replacing the -e from the parent
alkene's name with -yl.
• H2C=CH- (ethenyl or commonly known
as vinyl). The parent alkene was
H2C=CH2, ethene.
ALKYNYL GROUP
• An alkynyl group is a hydrocarbon
group formed when a hydrogen atom is
removed from an alkyne group.
• Alkenyl compounds are named by
replacing the -e from the parent
alkyne's name with -yl.
• ethynyl group, H C  C  derived from
ethyne, H C  C H is also called
ethynyl radical.
AROMATICS (ARENES)
• Arenes are cyclic hydrocarbons that contain three
single bonds and three double bonds conjugated in
a six-carbon ring.
• Arenes are usually derived from benzene.
• Another commonly used name for arenes is
aromatic hydrocarbons.
• Arenes are cyclic hydrocarbons with alternating
single and double bonds.
• Aromatic hydrocarbons are arenes based on
benzene.
BENZENE DERIVATIVES
• The nomenclature of substituted benzene ring
compounds is less systematic than that of the
alkanes, alkenes and alkynes.
• A few mono-substituted compounds are named by
using a group name as a prefix to "benzene", as
shown by the combined names listed below.
• A majority of these compounds, however, are
referred to by singular names that are unique.
• There is no simple alternative to memorization in
mastering these names.
BENZENE DERIVATIVES
ARYL GROUP
• aryl group , in chemistry, group of atoms
derived from benzene or from a benzene
derivative by removing one hydrogen
that is bonded to the benzene ring.
• The simplest aryl group is phenyl, C6H5 ;
it is derived from benzene.
ALKYL, ALKENYL, ALKYNYL and ARYL GROUPS
Hydrocarbons
Groups after one hydrogen removed
Name of
the Group
Formula
Name of the
Compound
Name of
the Group
Formula
Name of the
Substituent
Alkane
CH4
Methane
Alkyl
CH3 –
Methyl
C2H6
Ethane
C2H5 –
Etihyl
Cyclohexane
Alkene
Alkyne
CH2 = CH2
Etene
CH2 = CH – CH3
Propene
CH  CH
Ethyne
CH  C – CH3
Propyne
Arene
Benzene
CH3
Toluene
Naphtaline
Cyclohexyl
Alkenyl
Alkynyl
CH2 = CH –
Ethenyl(Vinyl)
– CH = CH – CH3
1-Propenyl
CH2 = CH – CH2 –
2-Propenyl (Allyl)
CH  C –
Ethynyl
CH  C – CH2 –
Propynyl
Aryl
Phenyl
CH2
Benzyl
naphthyl
FORMATION OF ALKANES AND ARENES
Alkyl, Alkenyl, Alkynyl and Aryl groups are not stable enough to exist
as alone.
• Their tendency is to join other groups and this bonding tendency is
the basis of synthetic organic chemistry.
• When alkyl groups join with each other alkanes will form:
CH3-CH3
CH3CH2-CH2CH3 CH3CH2- CH2CH2CH3
•
Ethane
Butane
Pentane
• When alkyl groups joined to aryl groups arenes will form. When we are
naming arenes (aromatic hydrocarbons) first the name of alkyl group is
said then the word benzene is added:
CH3
Methylbenzene ( Toluene )
C2H5
Ethylbenzene
FORMATION OF POLYCYCLIC ARENES
• When aryl groups join to each other
polycyclic arenes (polycyclic aromatic
hydrocarbons) will form.These
compounds are named by using their
common names.
Naphtaline
Anthracene
FORMATION OF ALKENES
•
•
•
1.
2.
3.
4.
When alkyl groups join to alkenyl groups alkenes will form. 2propenyl (CH2 = CH – CH2 -) and methyl ( CH3-) groups join 1butene will form:
CH2 = CH – CH2 – CH3
When we are naming alkenes according to IUPAC (Systematic
Naming) rules number the carbons in the chain so that the double
bond would be between the carbons with the lowest designated
number.
1
2
3
4
CH2 = CH – CH2 – CH3
When writing the name of the compound:
first the lower number of the carbon atom which makes the double
bond is written then
a hyphene (-) is drawn and
finally the name of the alkene corresponding to the parent chain(
the longest continuous chain of carbons that have the double
bond) is written.
1
2
3
4
1
2 3
4
CH2 = CH – CH2 – CH3
CH3- CH=CH - CH3
1- butene
2- butene
NAMING ALKENES
NAMING ALKENES
FORMATION OF ALKYNES
• When alkyl groups join to alkynyl groups alkynes will
form.
• For example: ethyl (C2H5-) and propynyl (CH  C – CH2 -)
groups joined to each other 1-pentyne will form:
1
2 3
4
5
CH  C – CH2 – CH2 – CH3
NAMING ALKYNES
1. Identify the longest continuous chain of carbon
atoms that contains the carbon-carbon triple bond.
The parent name of the alkyne comes from the
IUPAC name for the alkane of the same number of
carbon atoms, except the - ane ending is changed to
- yne to signify the presence of a triple bond. Thus, if
the longest continuous chain of carbon atoms
containing a triple bond has five atoms, the
compound is pentyne.
2. Number the carbon atoms of the longest continuous
chain, starting at the end closest to the triple bond.
Thus,
is numbered from right to left, placing the triple bond
between the second and third carbon atoms of the
chain. (Numbering the chain from left to right
incorrectly places the triple bond between the third
and fourth carbons of the chain.)
Naming Alkynes
3. The position of the triple bond is indicated by placing
the lower of the pair of numbers assigned to the triplebonded carbon atoms in front of the name of the
alkyne. Thus the compound shown in rule 2 is 2pentyne.
4. The location and name of any substituent atom or
group is indicated. For example, the compound
is 5-chloro-2-hexyne.
ALKYL HALIDES AND ALCOHOLS
• When halogens and alkyl groups join to each
other alkyl halides will form.
• In the functional groups table - I we can see
ethyl bromide as an example of an alkyl halide.
• Similarly when hydroxide and alkyl groups join
to each other alcohols will form.
• In the functional groups table - I we can see
propyl alcohol or propanol (C3H7 - OH) as a
combination of a propyl (C3H7 -) and hydroxide
(- OH) groups.When we are naming alcohols in
common naming syste,first the name of alkyl
group is written than the family name alcohol is
added.
FUNCTIONAL GROUPS
• Alkyl groups can also join with halogens and
other atoms or atom groups to form organic
ompounds other than hydrocarbons.
• Groups that are joined to alkyl grous which have
tendency to react chemically are called
Functional Groups.
• Functional groups will be represented in a table
in the next two slides. The R, R',R1,R2,R3 and R4
written as bold represent different alkyl groups.
• But R not written as bold are generally represent
alkyl groups and in some special cases it may
be hydrogen,H.
NAMES AND FORMULAS OF COMMON FUNCTIONAL
GROUPS AND DERIVED COMPOUNDS - I
Functional
Groups in
Compounds
Family
Name
General Formula
Formula of the Compund
as an Example
Name of the
Compound
R
Alkane
R  H or R  R
CH3 – CH3
Ethene
C=C
Alkene
R2  R1  HC = CH  R3  R4
CH3CH2CH = CHCH2CH3
3-hexene
CC
Alkyne
R1  C  C  R2
C2H5 – C  C – CH3
2-pentyne
Arene
R
CH3
Methyl
benzene
(Toluene)
X
(-F, -Cl, Br, -I)
Alkyl
Halide
R–X
C2H5 – Br
Ethyl bromide
 OH
Alcohol
R – OH
C3H7 – OH
Propyl alcohol
(propanol)
O
Ether
R – O – R'
CH3 – O – CH3
Dimethyl ether
O
O
Acetaldehyde
O
Aldehyde
C H
O
C
R C H
Ketone
CH3 C H
O
O
R C R'
CH3 C CH3
Propanone
(dimethyl
ketone)
NAMES AND FORMULAS OF COMMON FUNCTIONAL
GROUPS AND DERIVED COMPOUNDS - II
Functional
Groups in
Compounds
O
Family Name
carboxylic acid
C OH
H
Amine
N O
CN
O
Nitrile
RCN
Ester
O
O H
R C O R'
Amide
C N H
O
C X
Acyl halide
H
O
CH3
Propylamine
Nitromethane
N O
CH3  C  N
O
Ethanenitrile
Ethyl ethanoate
C2H5 C OCH3
O H
CH3
C N H
O
O
R C X
Propanoik acid
C3H7 N H
O H
R C N H
Name of the
Compound
C2H5 C OH
O
R N O
C O
O
H
R N H
Nitro alkane
Formula of the
Compund as an
Example
O
R C OH
N H
O
General Formula
CH3
C Cl
acetamide
(Ethanamide)
acetyl chloride
FUNCTIONAL GROUPS
FUNCTIONAL GROUPS
LEARNING CHECK
1. Draw the stuructural formula and write the
name of the compound made of ethyl(-C2H5)
and butenyl(CH2 = CH – CH2 – CH2-) grops.
2. Draw the stuructural formula of 2- pentene.
3. Draw the stuructural formula of isobutyl
chloride.
4. Write the IUPAC name of the structure:
CH3 – CH2 – C  C – C2H5
5. Draw the stuructural formula and then write
the name of the compound when the alkyl
CH
group 1,1-Dimethylethyl
and hydroxyl
3
CH3
C
CH3
group (- OH) join to each other.
PHYSICAL PROPERTIES OF HETEROATOMIC
ORGANIC COMPOUNDS
• Heteroatomic groups like hydroxide
(- OH), formyl(- CHO) and caboxyl(-COOH) can join to alkyl
groups.
• The physical properties of these heteroatomic compounds
are different than that of hydrocarbons having the same
number of carbon atoms.
• Due to changes in intermolecular forces based on
mass,volume and polarity changes) physical properties will
change.
• Alcohols,aldehydes and carboylic acids have higher melting
and boiling points than alkyl halides having the same number
of carbon atoms due to addition of hydrogen bonding to
dipole-dipole interactions.(Remember hydrogen bonding is
stronger interaction than dipole-dipole forces.)
LEARNING CHECK
Name
m.p
(ºC)
b.p
(ºC)
Butane
- 138
- 0.5
Butanol
- 88.6 117.7
Etoxyethane
(Dimethyl ether)
Butylamine
- 116
34.6
- 51
78
Try to explain the
differences in melting
and boiling points of
the compounds in the
given table by
comparing their
intermolecular forces.
PHYSICAL PROPERTIES OF HETEROATOMIC
ORGANIC COMPOUNDS
• When heteroatomic groups like hydroxide
(- OH), and caboxyl (- COOH) join to alkyl groups solubility
in water will increase since these hydrophilic groups are
polar.
Hydrofobic group Hydrophilic group
CH3- CH2- CH2 OH
propopyl alcohol
Hydrofobic group Hydrophilic group
CH3- CH2- CH2 COOH
butanoic acid
• On the other hand hydrocarbons having the same
number of carbon atoms with alcohols and carboxylic
acids do not dissolve in water since hydrophobes are
nonpolar molecules.
CHEMICAL PROPERTIES OF HETEROATOMIC
ORGANIC COMPOUNDS
• When heteroatoms are joined to alkyl groups
chemical reactivity will be greater than the
hydrocarbons having the same number of carbon
atoms.
• Saturated hydrocabons(Alkanes) can only give
substitution and combustion reactions.
• Alkenes and Alkynes are more reactive than
alkanes due to existance of pi bonding.So they can
also give addition reactions.
• Heteroatomic organic compounds can give other
types of reactions due to polar character of
heteroatomic part.
CHEMICAL PROPERTIES OF HETEROATOMIC
ORGANIC COMPOUNDS
• Funcional groups can be cations and anions in chemical
reactions.
• Acetyl group in the compound H3C – CO – Cl act as a
cation since acetyl chloride molecule is polar.
• Cl is partial negative and C is partial positive.
O
CH3
Acetyl
cation
C+
O
Cl
CH3
Chlorine
anion
C
Cl
Acetyl chloride
• In the compound Li – CH3 methyl group act as an
anion,since methyl lithium molecule is polar.
• CH3 is partial negative and Li is partial positive.
Li+ +
Lithium
cation
CH3Methyl
anion
LiCH3
Methyl lithium
CHEMICAL PROPERTIES OF HETEROATOMIC
ORGANIC COMPOUNDS
• In the polar compound Methyl fluoride
(Fluoromethane) CH3F methyl group act as a
cation and fluorine act as an anion.
CH3+
+
F-
Methyl
Fluorine
cation
anion
CH3F
Methyl fluoride
NAMING OF DIOLS AND TRIOLS
• Diols, hydroxyaldehydes ,
hydroxyketones,dicarbonyls,hydroxyacids,ketoacids and
dicarboxylic acids are the examples of organic compunds having
more than one functional groups.
• Diols (glycols) have two hydroxide (-OH) groups but triols
(glycerine) have three hydroxide groups.
• When naming these compounds the longest continuous chain
having hydroxide groups is chosen and numbering should start
from the end closer to hydroxide group.
• After writing the numbers of carbon atoms bonded to hydroxide
groups a hyphen is drawn and then the name of the hydrocarbon is
written according to the number of carbon atoms in the longest
chain.
• Finally the word diol or triol is added if the molecule has two or
three hydroxide groups respectively.
2 CH2OH
3 CH2OH
2 CHOH
1 CH2OH
1,2-Ethanediol
(Glycol)
1 CH2OH
1,2,3-Propanetriol
(Glycerine)
NAMING OF HYDROXYALDEHYDES AND
HYDROXYKETONES
• Hdroxyaldehdes and hdroxyketones have both
hydroxide (- OH) and carbonyl( C=O ) groups.
• When naming these compunds the carbon atom having
the double bonded should be located to the lowest
possible number.
CH3
1 2
3 4
CH3 C CH2 C OH
5
CH3
O
OH
O
1 2
3 4
CH3 CH CH2 C H
3-Hydroxybutanal
4-Hydroxy-4-methyll-pentane2-on
(Diaceton alcohol)
NAMING OF DICARBONYL COMPOUNDS
• Dicarbonyl compounds are dialdehydes,aldehyde-ketone and
diketones.
• When naming these compounds the longest chain is
numbered in such away that the carbonyl group should be
located to the lowest possible number.
• After writing the numbers of carbon atoms bonded to oxygen
atoms a hyphen is drawn and then the name of the
hydrocarbon is written according to the number of carbon
atoms in the longest chain.
• Finally do not forget to add the suffixes - dione,- trione,- dial
and – trial depending on the the type and number of
functional groups.
• –al suffix will be used for aldehyde and -one suffix will be
used for ketone.
O
1 2
5
3 4
CH3 C CH2 C CH3
O
2,4-Pentandione
Acetylacetone
O
3
2
1
4
H C CH2 CH2 C H
O
1,4-Butanedial
Succinindialdehy
de
NAMING OF KETOACIDS
• Ketoacids are the carbonyl group containing carboxylic
acids.
• When naming these compounds the longest chain is
numbered in such a way that the carboxylic acid should be
located to the lowest possible number.
• Carbonyl group is defined by oxo- (=O) prefix.
• Write the name of the hydrocarbon according to the number
of carbon atoms in the longest chain and then add the suffix
–oic acid.
O
CH3
C
COOH
2-Oxopropanoic acid
Pirüvik asi
O
4
3
CH3 C
2
1
CH2 COOH
3-Oxobutanoic acid
Acetoacetic acid
NAMING OF HYDROXYACIDS
• Hydroxy acids are the compounds having both
hydroxyl(-OH) and carboxyl (-COOH) groups.
• When naming these compounds the longest chain is
numbered in such a way that the carboxylic acid should
be located to the lowest possible number.
• After writing the number of carbon atom which is
bonded to hydroxyl group a hyphene is added.
• Then hydroxy prefix is written, the name of the
hydrocarbon according to the number of carbon atoms
in the longest chain and the suffix –oic acid is added.
COOH
COOH
H C OH
H C OH
H C H
H
2-Hydroxypropanoic acid
Lactic acid
OH C H
COOH
2,3-Dihydroxyibutanedioic
acid
Tartaric acid
COOH
H C OH
CH2
COOH
Hydroxybutanedioic acid
Malic acid
NAMING OF DICARBOXYLICACIDS
• Dicarboxylic acids are the compounds having
two carboxyl groups in their molecules.
• When naming them, write the name of the
hydrocarbon according to the number of carbon
atoms in the longest chain and then add the
suffix –dioic acid.
O O
OH C C OH
Ethanedioic
acid
Oxalic acid
O
OH C CH2 CH2
Butanedioic
acid
Succinic acid
O
C OH
CONDENSED STRUCTURAL
FORMULAS
• Chemical structures may be written in more compact
forms, particularly when showing organic molecules.
• In condensed structural formulas, many or even all
of the covalent bonds may be left out, with
subscripts indicating the number of identical groups
attached to a particular atom.
• Two varieties of condensed structural formula, both
showing butane:
SKELETAL ( BOND-LINE ) FORMULA
• Another shorthand structural diagram is the skeletal
formula (also known as a bond-line formula or
carbon skeleton diagram).
• In skeletal formulae, carbon atoms are not signified
by the symbol C but by the vertices of the lines.
• Hydrogen atoms bonded to carbon are not shown —
they can be inferred by counting the number of
bonds to a particular carbon atom — each carbon is
assumed to have four bonds in total, so any bonds
not shown are, by implication, to hydrogen atoms.
• A skeletal diagram of butane:
SKELETAL ( BOND-LINE ) FORMULA
• For example, in the image below, the skeletal
formula of hexane is shown.
• The carbon atom labelled C1 has only one bond
shown to it, so there must also be three hydrogens
bonded to it, in order to make its total number of
bonds four.
• The carbon atom labelled C3 has two bonds to other
carbons and is therefore bonded to two hydrogen
atoms as well.
BALL-AND-STICK MODEL
• A ball-and-stick model of the actual molecular
structure of hexane, as determined by X-ray
crystallography, is shown for comparison, in which
carbon atoms are depicted as black balls and
hydrogen atoms as white ones.
COMPARISON OF DIFFERENT
MODELS
• Shown below for comparison are a ball-and-stick
model of the actual three-dimensional structure of
the ethanol molecule in the gas phase (determined
by microwave spectroscopy, left), the Lewis
structure (centre) and the skeletal formula (right).
BOND-LINE FORMULAS OF SOME ORGANIC
Bazı organik bileşiklerin iskelet (çizgi-bağ) formülleri
COMPOUNDS
Name of the
compound
Isohexane
Molecular
formula
C6H14
Stuructural
Formula
Bond-Line Formulas
CH3 CH2 CH3
CH CH2
CH3
Ethyl acetate
(Ethyl
ethanoate)
CH3CO2C2CH5
O
C
CH3
Acetophenone
O
C6H6COCH3
CH2
O
CH3
O
O
C
CH3
Neopentane
C5H12
CH3
CH3
C
CH3
O
CH3
LEARNING CHECK
1. Name the following compounds represented
by the bond- line formulas:
OH
2. Draw the stuructural formulas of the following
compounds and then write their bond-line
formulas:
a) ethyl ethanoate
b) 1- aminobutane
c) 2- chloro- 4 - methylheptane
REFERENCES
•
•
•
•
•
•
•
•
•
•
•
•
•
•
•
http://chemed.chem.purdue.edu/genchem/topicreview/bp/1organic/1org_fr
ame.html
http://en.wikipedia.org/wiki/Hydrocarbon
http://www.elmhurst.edu/~chm/vchembook/500hydrocarbons.html
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/nomen1.htm
http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/functio
n.html
http://en.wikipedia.org/wiki/Functional_group#Table_of_common_function
al_groups
http://en.wikibooks.org/wiki/Organic_Chemistry/Overview_of_Functional_
Groups
http://www.tamug.edu/mars/chem227/functgrtbl.htm
http://masterorganicchemistry.com/2011/02/14/table-of-functional-grouppriorities-for-nomenclature/
http://www.chemistry-drills.com/functional-groups.php?q=simple
http://www.ausetute.com.au/fungroup.html
http://www.ausetute.com.au/usehydrc.html
http://en.wikipedia.org/wiki/Aromatic_hydrocarbon
http://en.wikipedia.org/wiki/Simple_aromatic_ring
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/nomen1.htm
REFERENCES
• http://en.wikipedia.org/wiki/Lewis_structure
• http://en.wikipedia.org/wiki/Skeletal_formula
• http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemis
try
• http://www.physchem.co.za/OB12-mat/organic2.htm
• http://dl.clackamas.edu/ch106-01/alkyl1.htm
• http://www.personal.psu.edu/the1/nomencl.htm
• http://www.personal.psu.edu/faculty/t/h/the1/chem/Nomenclature/ind
ex.html#12
• http://www.vanderbilt.edu/AnS/Chemistry/Rizzo/chem220a/alkenes.p
df
• http://www.cliffsnotes.com/study_guide/AlkynesNomenclature.topicArticleId-22667,articleId-22630.html
• http://www.angelo.edu/faculty/kboudrea/organic/IUPAC_Handout.pdf
• http://www.angelfire.com/bc2/OrgChem/alkenes.html
• http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/nomen1.ht
m
• http://en.wikipedia.org/wiki/Functional_group