ORGANIC
CHEMISTRY
ORGANIC CHEMISTRY
branch of chemistry that deals
with carbon-containing
compounds with: H, O, P, N, S,
X (halides)
CARBON
only element that can bind to itself
contains 4 binding sites for other atoms to
attach to it
these 4 binding sites, when bonded with
other atoms/molecules form a tetrahedron
found in group 4, period 2
atomic number: 6
1s22s22p2
needs 4 more electrons to complete
its octet
valence: 4
neither donate or receives electrons
can only share: covalence
HYDROCARBONS
Aliphatic - single chain, no ring/s involved
Saturated: single bonds only (Ex: Alkanes)
Unsaturated: has multiple bonds (Ex: Alkenes
& Alkynes)
Aromatic - presence of ring/s, specifically
benzene ring and its derivatives
Examples: Benzene, Naphthalene,
Anthracene
Alicyclic or Carbocyclic - they are
chains that form a ring and behave
like aliphatics (single bond)
Examples: cyclopropane, cyclobutane,
cyclopropene, cyclobutene
HUCKEL'S RULE
used to determine if a compound is
aromatic or not
4n + 2 = eNote: If n = whole number, then substance
is aromatic
HYDROCARBON DERIVATIVES
are hydrocarbons that bear
other carbon and hydrogen
atoms and other elements
such as oxygen, nitrogen,
sulfur or halogen, etc.
1. Halogen-containing
Alkyl halides (RX)
Aryl halides (Aromatic ring - X)
2. Oxygen-containing
Alcohol/ phenol, ether, aldehyde
and keton
Carboxylic acids and their
derivatives (esters, amides,
anhydrides, acid/acyl chloride)
3. N-containing
Amines
Heterocyclic N-compounds
4. S-containing
Thiols
Thioethers
Thiophenols
SIMPLE HYDROCARBONS
Chain or series of HC
Classification:
Alkanes
Alkenes
Alkynes
SYSTEMS OF NOMENCLATURE
Common
uses the name given when it was
discovered
eg. Formic acid (Latin, formica = ants)
uses prefixes: -n, -iso, -neo
Derived Names - derived from a
parent compound
IUPAC - International Union of Pure and
Applied Chemistry
most systematic
eg. 2-methylhexane
based on:
A. longest continuous C chain or parent chain
B. use of numbers
C. use of C # prefixes
No. of C
atoms
Prefix
No. of C
atoms
Prefix
meth
hex
eth
hept
prop
oct
but
non
pent
10
dec
IUPAC RULES
Name by considering the longest
chain
Number C atoms consecutively from
one end so that the branches or
substituents are given the lowest
position numbers
Identify the substituents and indicate
the positions by using numbers
If there is more than one of the
same substituent/alkyl group on
the chain, indicate the number of
groups by using prefixes: di, tri,
tetra and so on.
ALKANES
also called paraffins/ saturated
hydrocarbons
Nomenclature Rules for Alkanes
General Formula: CnH2n+2
Contain only C-C single bonds
Suffix is -ane, -yl for alkyl
Name of the parent chain:
Eg. Meth + ANE = methane
# C Rootword
+ "ane"
Formula
Dehydrogena
ted
1
meth
methane
CH4
methyl
ethane
C2H6
ethyl
propane
C3H8
propyl
butane
C4H10
butyl
pentane
C5H12
pentyl
eth
prop
but
pent
ALKYL GROUPS (R)
are alkanes with one hydrogen
atom removed.
CH4 ----> -CH3 (methyl)
Can participate in van der waals
interaction and hydrophobic bonding
Metabolism: oxidation
Aryl Groups (Ar) - an aromatic
(benzene ring) with a hydrogen atom
removed.
Reactions to Consider
Combustion - a chemical
reaction in which HC burns
(rapid oxidation) and produces
carbon dioxide and water.
Cycloalkanes
Cyclopropane or trimethylene
Cyclobutane
Cyclopentane
Ways of Representing the Structure of
Molecules and Classes of Formulae
Empirical Formula - the simplest
possible formula showing the whole
number stoichiometric ratio of the
different atoms (elements) in the
compound.
Ex: Propane is C3H8
2-methylpropane is C2H5
Molecular Formula summarizes all the atoms in
the molecule but does not
show their arrangement at all.
Ex: Propane is C3H8
2-methylpropane is C4H10
Shortened or Abbreviated
Formula - shows how groups of
atoms are linked or sequenced in
a molecule.
Ex: Propane is CH3CH2CH3
Methylpropane is (CH3)3CH
Butane is CH3CH2CH2CH3
Full Structure - gives a '2D'
projection-representation of
the molecule and must
clearly show how all the
atoms are connected
Stereochemical Formula - the
full structural/graphical/displayed
formula in terms of the 3D
structural or spatial arrangement
of the atoms.
ALKENES
Nomenclature Rules for Alkenes
contain at least one double bonded
carbon pair
they follow the same naming
convention used for alkanes
end in "ene"
General Formula: CnH2n
Naming Alkenes
Name an alkene by considering its
longest carbon chain that contains
double bond.
Number the longest continuous chain
starting from the end that gives the
lowest number to the position of the
double bond.
Indicate the position of the attached
alkyl group/s by name and number.
If there is more than one of the same
substituent/alkyl group on the chain,
indicate the number of groups by
using prefixes.
Forces involved
Van der waals interaction
Hydrophobic bonding
Metabolism:
more reactive than alkyl groups
hydration
epoxidation
peroxidation
reduction
ALKADIENES
contain 2 C=C
name: indicate the position of
double bond + prefix + diene
CH2=CHCH=CH2
ALKYNES
Hydrocarbons that bear 2 or
more carbon atoms sharing a
triple bond
General Formula: CnH2n-2
OTHER FUNCTIONAL GROUPS
Halides
process is called halogenation
formation of an alkyl or aryl halide
functional group: R-X
example: -F, -Cl, -Br, -I
