ORGANIC COMPOUNDS

Learning Competency
Describe the different functional groups
(STEM_GC11OCIIg-j-87)
Specific Objectives:
1. Describe the major functional groups in organic
chemistry and name organic compounds;
2. Recognize from the structural formula which
class of organic compounds a certain molecule
belongs; and
3. Identify all the functional groups present in a
molecule given its structural formula.
• Organic chemistry is the study of the chemistry of carbon-
containing compounds.
• Organic compounds are compounds containing one or
more atoms of carbon EXCEPT oxides of carbon (e.g., CO
and CO2); carbides (e.g., CaC2, commonly known as
“kalburo”); cyanides (e.g., NaCN); carbonates (e.g., CaCO3);
hydrogen carbonates or bicarbonates (e.g., NaHCO3); and
allotropes of carbon (e.g., diamond, graphite, graphene,
and fullerenes such as buckminsterfullerene, or C60).
• Carbon can form four covalent bonds. It forms strong
bonds with a variety of elements, especially H, O, N, and
the halogens. Carbon also has an exceptional ability to
bond to another carbon atom/s forming a variety of
molecules made up of chains (straight/unbranched,
branched, or cyclic) of carbon atoms in endless arrays.
vMolecular formula is a chemical formula that
indicates the actual numbers of atoms present in a
molecule. For example, the molecular formula CH4
for methane tells us that methane has one carbon
atom and four hydrogen atoms.
vStructural formula displays the atoms of the
molecule in the order they are bonded. It also
depicts how the atoms are bonded to one another.
There are four types of structural formulas:
electron-dot formula, dash formula, condensed
formula, and bond-line formula or skeletal formula.
Examples of these four types are shown below
using 1-propanol as an example.
A. Dash Structural Formula
ØDash formulas have lines that show bonding electron
pairs and include elemental symbols for all the atoms in a
molecule.
Ø If we look at Fig.1b-d, we find that the chain of atoms
in those formulas is “straight.” Fig.1a and Fig.1e
correspond more accurately to the actual shape of the
molecule where the chain of atoms is “not at all straight.”
A better description is unbranched.
Ø Atoms joined by single bonds can rotate relatively freely
with respect to one another.
Ø The relatively free rotation of single bonds mean that
the chain of atoms can assume a variety of arrangements.
Consider the dash formulas of 1-propanol.
HYDROCARBONS
• Hydrocarbons are compounds
that contain only carbon and
hydrogen atoms.
Hydrocarbons are further
classified into aliphatic
hydrocarbons (those that do
not contain benzene ring) and
aromatic hydrocarbons (those
that contain benzene ring).
Names of hydrocarbons end
in -ane, -ene, or -yne which
then tell us what kinds of
carbon–carbon bonds are
present. The name of the
parent compound is
determined by the number of
carbon atoms in the longest
chain.
5
A. Alkanes contain only carbon-carbon single
bond (C―C), and this is indicated in the
family name and in names for specific
compounds by an -ane ending.
Ø Alkanes, except cycloalkanes, have the
general formula CnH2n+2 where n=1, 2, 3, ....
ØThey are also known as saturated
hydrocarbons because these compounds
contain the maximum number of hydrogen
atoms that can bond to carbon atoms
present; that is, they are saturated with
hydrogen atoms.
• Alkyl Groups and the Symbol R
Ø Alkyl groups are the groups that would be
obtained by removing a hydrogen atom from an
alkane. These groups are identified for the
purpose of naming compounds. These alkyl
groups have names that end in -yl.
ØWhen the alkane is unbranched, and the
hydrogen atom that is removed is a terminal
hydrogen atom, the names are straight forward.
Examples of unbranched alkyl groups are
methyl, ethyl, propyl and butyl.
Ø Methyl group can be derived from methane
by removing one H atom. Ethyl group can be
derived from ethane after the removal of one H
atom attached from any of the two C atoms.
Ø For alkanes with more than two carbon
atoms, more than one alkyl groups can be
derived. Two alkyl groups can be derived from
propane. (1) Removal of one terminal H atom
forms an unbranched alkyl called propyl group;
(2) removal of one H atom from the middle C atom
forms a branched alkyl called 1-methylethyl
(systematic name) or isopropyl group (common
name).
Alkyl Halides or Haloalkanes
ØAlkyl halides or haloalkanes are compounds in
which halogens (fluorine, chlorine, bromine, or
iodine) replaces a hydrogen atom of an alkane.
ØAlkyl halides or haloalkanes have the general
formula RX where X = F, Cl, Br, or I. In naming
compounds with halogen substituents, we use fluoro,
chloro, bromo, and iodo.
ØAlkyl halides are classified as being primary (1°),
secondary (2°), or tertiary (3°). (We do not say first
degree, second degree, or third degree, but rather we
say primary, secondary, or tertiary.) This
classification is based on the carbon atom to which
the halogen is directly attached.
A. 1° Alkyl halide – If the carbon atom that bears the
halogen is directly attached to only one other carbon,
the carbon atom is said to be a primary carbon and the
alkyl halide is classified as a primary alkyl halide.
B. 2° Alkyl halide – If the carbon that bears the
halogen is itself directly attached to two other carbon
atoms, then the carbon is a secondary carbon and the
alkyl halide is a secondary alkyl halide.
C. 3° Alkyl halide - If the carbon that bears the
halogen is directly attached to three other carbon
atoms, then the carbon is a tertiary carbon and the
alkyl halide is a tertiary alkyl halide.
Nomenclature of Alkanes
Ø Today, chemists use a systematic nomenclature
developed and updated by the International Union
of Pure and Applied Chemistry (IUPAC). Underlying
the IUPAC system is a fundamental principle: each
different compound should have a different and
unambiguous name.
Ø In IUPAC substitutive nomenclature a name
may have as many as four features: locants,
prefixes, parent compound, and suffixes.
3. Cycloalkanes with one ring and two or more
substituents: For a ring with two substituents,
begin by numbering the carbons in the ring,
starting at the carbon with the substituent that is
first in the alphabet and number in the direction
that gives the next substituent the lower number
possible. When there are three or more
substituents, begin at the substituent that leads to
the lowest set of numbers (locants). The
substituents are listed in alphabetical order, not
according to the number of their carbon atom.
B. Alkenes contain at least one carbon-carbon double
bond (C═C), and this is indicated in the family name and
in names for specific compounds by an -ene ending.
ØAlkenes, also called olefins, have the general formula
CnH2n where n=2, 3, ....
ØAlkenes are classified as unsaturated hydrocarbons as
opposed to alkanes which are saturated hydrocarbons.
ØExamples are ethene (C2H4) and propene (C3H6) – the two
simplest alkenes.
ØAlkenyl halide is a compound with a halogen atom
bonded to an alkene carbon. In older nomenclature such
compounds were sometimes referred to as vinyl halides.
 Nomenclature of Alkenes
and Cycloalkenes

ØThe IUPAC rules for naming alkenes are

similar in many respects to those for naming
alkanes:
1. Determine the parent name by selecting the
longest chain that contains the double bond
and change the ending of the name of the
alkane of identical length from -ane to -ene.
Thus, if the longest chain contains five carbon
atoms, the parent name for the alkene is
pentene; if it contains six carbon atoms, the
parent name is hexene, and so on.
4. Number substituted cycloalkenes in the way that
gives the carbon atoms of the double bond the 1 and 2
positions and that also gives the substituent groups the
lower numbers at the first point of difference. With
substituted cycloalkenes it is not necessary to specify
the position of the double bond since it will always begin
with C1 and C2. The two examples shown here illustrate
the application of these rules:
C. Alkynes contain at least one
carbon-carbon triple bond (C≡C),
and this is indicated in the family
name and in names for specific
compounds by an -yne ending.
ØAlkynes have the general formula
CnH2n-2 where n=2, 3, ...
ØTogether with alkenes, alkynes
are considered unsaturated
hydrocarbons.
Ø Examples are ethyne (C2H2,
commonly called acetylene),
propyne (C3H4), and butyne (C4H6).