Organic

Chemistry
 Organic Compounds
• The study of carbon & carbon compounds
• Are the primary constituents of all living organisms.

Χ●
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Χ CΧ●
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Note: Carbon is able to form 4 covalent bonds (4 valence

electrons) with other carbon or other elements.
 Types of Bonds Types of
Compounds
Single Bond single covalent bond Saturated
in which they share 1
pair of electrons
Double Bond carbon atoms may
share 2 pairs of
electrons to form a
double bond.
Unsaturated
Triple Bond carbon atoms may
share 3 pairs of
electrons to form a
triple bond.
 Organic Compounds Inorganic Compounds
Many are gases, liquids or solids Most are solids

May contain carbon. Contain

Usually always contain carbon, metal and other elements. Does
especially carbon-hydrogen bonds not contain carbon-hydrogen
bonds.

Generally found in living matter, Generally obtained from non-living

i.e., animals and plants. matter, i.e., minerals.

Biological in nature Mineral in nature

Many are gases, liquids or solids Most are solids

Most form ionic bond, some

Form covalent bonds
covalent bonds are present

Lower melting and boiling points Higher melting and boiling points
 Organic Compounds Inorganic Compounds
Insoluble in water, soluble in Readily soluble in water, insoluble
organic solvents in organic solvents

Highly inflammable and volatile Not inflammable and non – volatile

Include salts, metals, substances

made from single elements and
Include nucleic acids, fats, sugars,
any other compounds that don't
proteins, enzymes and many fuels.
contain carbon bonded to
hydrogen.

Examples: methane, ethane,

Examples: carbon dioxide,
acetylene, alcohols, carbon
sulphuric acid, NaCl, diamond
tetrachloride (CCl4), urea
(pure carbon)
[CO(NH2)2]
 Terms
• Molecular Formula - tells you the actual number of
each kind of atom within that molecule (ex. H2O)
• Structural Formula - tells you something about the
arrangement of atoms within the molecule (ex. H-O-
H)
• Condensed Structural Formula - system of writing
organic structures in a line of text (ex. Ethane
CH₃CH₃)
• Isomers – same molecular formula but different in
structures
“R” – alkyl group “X” - halogens
 Alkanes
• Organic compounds that consist entirely of single-
bonded carbon and hydrogen atoms and lack any
other functional groups and a saturated
hydrocarbons
• simplest and least reactive hydrocarbon species
containing only carbons and hydrogen's
• principal constituent of gasoline and lubricating oils
• subdivided into the following three groups:
the linear straight-chain alkanes, branched
alkanes, and cycloalkanes
• General formula CnH2n+2
CH3(CH2)3CH3
 Isomers
• the boiling and melting points of the branched
isomers of any alkane are lower than their
unbranched counterpart.
• The branched isomers burn smoothly in air, while the
straight chain, i.e., unbranched isomers do not.
• if they are isomers of different homologous series,
they would show difference in both physical and
chemical properties.
 Isomers
Isomers of Alkane
Methane 1
Ethane 1
Propane 1
Butane 2
Pentane 3
Hexane 5
Heptane 9
Octane 18
Nonane 35
Decane 75
 Isomers

n-butane 2-methylpropane
 Isomers of Pentane
C5H12
n-pentane CH3CH2CH2CH2CH3

2-methyl butane isopentane -

CH3CH2CH(CH3)CH3

2,2 - neo pentane -

dimethylpropane CH3C(CH3)2CH3
 Isomers of Hexane
C6H14
1 CH3CH2CH2CH2CH2CH3 2

3 CH3CH2CH(CH3)CH2CH3 4

5 CH3CH(CH3)CH2CH2CH3 6

2,3-dimethyl butane 7 8

9 CH3C(CH3)2CH2CH3 10
 Isomers of Hexane
C6H14
n-hexane CH3CH2CH2CH2CH2CH3

3-methyl pentane CH3CH2CH(CH3)CH2CH3

2-methyl pentane CH3CH(CH3)CH2CH2CH3

2,3-dimethyl butane CH3CH(CH3)CH(CH3)CH3

2,2-dimethyl butane CH3C(CH3)2CH2CH3

 Alkyl Group
• group of carbon and hydrogen atoms derived from
an alkane molecule by removing one hydrogen
atom
• The name of the alkyl group is derived from the
name of its alkane by replacing the - ane suffix with
- yl,
• General formula -CnH2n+1
• e.g. methyl, CH 3 from methane CH 4
ethyl, C2H 5 from ethane C2H 6
• names are similarly based on the names of
corresponding alkane molecules
• a capital R- is used to represent that unspecified
alkyl group
Butane Butyl
 Naming Organic
Compounds
International Union of Pure and Applied Chemistry
(IUPAC)
- recognized authority for chemical standards of
nomenclature, measurements, and atomic mass
values.
 IUPAC Rules (Alkanes)
1. Identify the longest carbon chain. This chain is called
the parent chain.
2. Identify all of the substituents (groups appending from
the parent chain).
3. Number the carbons of the parent chain from the end
that gives the substituents the lowest numbers. When
compairing a series of numbers, the series that is the
"lowest" is the one which contains the lowest number at
the occasion of the first difference. If two or more side
chains are in equivalent positions, assign the lowest
number to the one which will come first in the name.
4. If the same substituent occurs more than once, the
location of each point on which the substituent occurs
is given. In addition, the number of times the substituent
group occurs is indicated by a prefix (di, tri, tetra, etc.).
5. If there are two or more different substituents they are listed in
alphabetical order using the base name (ignore the prefixes).
The only prefix which is used when putting the substituents in
alphabetical order is iso as in isopropyl or isobutyl. The prefixes
sec- and tert- are not used in determining alphabetical order
except when compared with each other.
6. If chains of equal length are competing for selection as the
parent chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in
the smaller side chain.
d)the chain having the least branched side chains.
7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo-
which appears directly in front of the base name.
Note:
The name of the compound is written out with the
substituents in alphabetical order followed by the
base name (derived from the number of carbons in
the parent chain). Commas are used between
numbers and dashes are used between letters and
numbers. There are no spaces in the name.
 Carbon Classification
• Primary carbons (1˚)- are carbons attached to one other
carbon. (Hydrogens – although usually 3 in number in this
case – are ignored in this terminology, as we shall see).
• Secondary carbons (2˚) - are attached to two other
carbons.
• Tertiary carbons (3˚) - are attached to three other
carbons.
• Quaternary carbons (4˚) are attached to four other
carbons.

Note: You can’t go higher than that. To have five

substituents, you’d need 10 electrons around carbon, a
clear violation of the octet rule.
 Haloalkanes
• Also called “Alkyl Halides”
• Compounds, which contain a halogen (F, Cl, Br or I)
• General formula of R-X
Chlorofluorocarbons (CFCs )
• non-flammable and not very toxic
• compounds containing carbon with chlorine and
fluorine atoms attached
• refrigerants, propellants for aerosols, for generating
foamed plastics like expanded polystyrene or
polyurethane foam, and as solvents for dry cleaning
and for general degreasing purposes.
• largely responsible for destroying the ozone layer
 Naming (Alkyl Halides)
1. Number the parent chain to give the substituent
encountered first the lowest number, whether it is
halogen or an alkyl group.
2. Indicate halogen substituents by the prefixes fluoro-
, chloro-, bromo-, and iodo- and list them in
alphabetical order with other substituents.
3. Locate each halogen on the parent chain by
giving it a number preceding the name of the
halogen.
Examples:

The parent chain is

still butane; now,
numbering the carbons, When the chlorines
such that the chlorine are on the same
The parent chain in this atoms are on carbons #1 & carbon, they are still
#2. Since there are two
example is butane; chlorines, the given the lowest
numbering the term dichloro- is used. number, and the
carbons, such that However, to specify the number is used
exact position of the two twice: 1,1-Dichloro.
the chlorine will be on chlorine atoms, the
When added to the
carbon #1 will result in numbers are used: 1,2- parent chain, butane,
Dichloro- is combined with
the name: butane to become the full, the name becomes:
1-Chlorobutane IUPAC name: 1,1-Dichlorobutane
1,2-Dichlorobutane
Seatwork:
Name the following Alkyl Halides:
 Cycloalkanes
• Cyclic hydrocarbons
• carbons of the molecule are arranged in the form
of a ring
• smallest cycloalkane is cyclopropane.
• may have multiple substituents
or functional groups that further determine their
unique chemical properties

Glucose Ribose Cholesterol

(6 carbon sugar) (5 carbon sugar) (polycyclic)
 Naming Cycloalkanes
The following rules must be followed in order.
1) The ring will be the parent chain (even if there is a longer linear chain attached to the
ring). The ring is named by the number of carbons (as before) but with the prefix cyclo-.
i.e. cyclohexane (six-carbon ring) or cyclooctane (eight-carbon ring)

2) Number the ring starting from the carbon with the substituent lowest in the alphabet.
Number in the direction that give the lower overall substituent numbers. (In more complex
situations go in the direction that is alphabetical).

3) Name any groups (substituents) attached to the parent ring.

-carbon substituents are named methyl, ethyl, propyl etc.
-halogen substituents are named fluoro, chloro, bromo etc.

4) Groups repeated substituents together using prefixes: di-, tri-, tetra- etc.

5) List the substituents in alphabetical order ignoring the prefixes.

i.e. ethyl before methyl
ethyl before dimethyl
6) Write out the name in the format:
#,#-prefixsubstituent-#-prefixsubstituentparentchain
• If there is an alkyl straight chain that has a greater
number of carbons than the cycloalkane, then the
alkyl chain must be used as the primary parent
chain. Cycloalkane acting as a substituent to an
alkyl chain has an ending "-yl" and, therefore, must
be named as a cycloalkyl.