ORGANIC CHEMISTRY:

ALKANES
What is Organic Chemistry ?
 The study of the compounds of carbon.
 Some carbon compounds are not considered to be
organic, such as CO2, CO, salts of carbon-
containing polyatomic ions (e.g., CO32-, CN-).
 Inorganic chemistry is the study of the other
elements and non-carbon containing compounds
Carbon
 Carbon is unique since it can form single, double, & triple
bonds with itself and with other atoms
 Carbon atoms can form stable bonds to many other
elements (H, F, Cl, Br, I, O, N, S, P, etc.). Most organic
compounds contain a few hydrogens, and sometimes
oxygen, nitrogen, sulfur, phosphorus, etc.
 Carbon atoms can form complex structures, such as long
chains, branched chains, rings, chiral compounds, etc.
 Because of this variety in bonding and complexity, carbon
atoms can form a tremendous variety of compounds.
Hydrocarbon: Alkane
 A hydrocarbon is a compound
consisting of only hydrogen (H) and
carbon (C).
 The carbon to carbon can be single,
double , or triple bonds.
 Alkanes are hydrocarbons with only
single bonds.
 Alkane: saturated hydrocarbons
(CnH2n+2)
 Saturated: only single bonds
 They are also called aliphatic
compounds
Structure
 Saturated hydrocarbons can be:
 linear (general formula CnH2n + 2)
 branched (general formula CnH2n + 2, n > 3)
 cyclic (general formula CnH2n, n > 2).
 The former two are alkanes, whereas the
third group is called cycloalkanes.
 Shape
 tetrahedral about carbon
 all bond angles are approximately 109.5°
 The simplest possible alkane (the parent
molecule) is Methane (CH4).
Drawing Alkanes
 When a structure is drawn to show each
bond, it is called a complete structural
formula (expanded structural formula).
 In condensed structural formulas,
only specific bonds are shown; this is
useful in reducing the number of C—H
bonds that must be drawn
 In line drawings (line-angle formulas),
bonds are represented by lines;
everywhere two lines meet or a line
begins or ends is a C atom. H’s on C’s
are not shown (except for emphasis). H’s
on other atoms must be shown
Example: Drawing Alkane
 Draw acceptable condensed structures and line drawings
associated with the following expanded structural formulas
Alkane Nomenclature
 IUPAC (International Union of Pure and Applied Chemistry) Rules
for Alkane Nomenclature
 Find and name the longest continuous carbon chain. This is called the parent
chain. (Examples: methane, propane, etc.)
 Number the chain consecutively, starting at the end nearest an attached group
(substituent).
 Identify and name groups attached to this chain. (Examples: methyl-, bromo-,
etc.)
 Designate the location of each substituent group with the number of the carbon
parent chain on which the group is attached. Place a dash between numbers
and letters. (Example: 3-chloropentane)
 Assemble the name, listing groups in alphabetical order.

    The prefixes di, tri, tetra etc., used to designate several groups of the
same kind, are not considered when alphabetizing. Place a comma
between multiple numbers. (Example: 2,3-dichloropropane)
Step 1: Find the parent chain.
 Where is the longest continuous chain of
carbons ?

Substituents - Parent
The Parent tells us how many carbon atoms
can be found in the longest chain.
The substituents indicate any groups that are
attached to the longest carbon chain.
Prefixes for # of Carbons

1 Meth 6 Hex

2 Eth 7 Hept

3 Prop 8 Oct

4 But 9 Non

5 Pent 10 Dec
Ending
 Alkanes (all C-C single bonded parent chain) end
in –ane
 Methane CH4
 Ethane C2H6
 Propane C3H8
 Attached carbon groups (substituents) end in –yl
 Methyl CH3 -
 Ethyl CH3CH2-
 Propyl  CH3CH2CH2 –  
Step 2: Number the parent chain.
 Number the parent chain so that the attached
groups are on the lowest numbers (

Methyl is on carbon #2 of the parent chain

Methyl is on carbon #4 of the parent chain
1 2 3 4 5
5 4 3 2 1
GREEN is the
right way for this
one!
 If two or more alkyl groups are attached to the longest
chain, use the numbering path that gives the lowest
number for the first point of difference.
 If two different alkyl groups are attached at the same
distance from either end of the chain, the one that comes
first in alphabetical order has the highest priority.
 If there is more than one way to get a certain number of
atoms in the longest chain, go with then way that gives
more substituents.

H3C
CH CH2 CH3
CH3
H3C CH2 C CH CH2 CH2 CH3
CH3
Step 3: Name the attached groups.
 Carbon (alkyl) groups
 Methyl CH3 -
 Ethyl CH3CH2-
 Propyl CH3CH2CH2 –
 Halogens
 Fluoro (F-)
 Chloro (Cl-)
 Bromo (Br-)
 Iodo (I-)
Step 4: Designate where the group is
attached to the parent chain.
 Use the numbers of the parent chain from step 2 to
designate the location of the attached groups to the
parent chain.

1 2 3 4 5
Step 5: Alphabetize the groups,
combine like groups, and assemble.
 Use a numerical prefix to indicate when more
than one of a same substituent exists in the
molecule)
 Prefixes are not considered when alphabetizing
(Example: dimethyl = m for alphabetizing)
 Parent chain goes LAST: The substituents are listed
alphabetically before the parent

Comma: numeral,numeral
Dash: numeral-letter or
letter-numeral
Numerical Prefixes for Naming
Identical Groups
Example: IUPAC Nomenclature
 Provide acceptable IUPAC names for the following molecules
 Give the names of the following compounds using
IUPAC nomenclature
 Draw Some Simple Alkanes:
 2-methylpentane
 3-ethylhexane
 2,3-dimethylbutane

 Draw condensed structural formulas or line

drawings for each of the following compounds
 3-ethylpentane
 2,2-dimethylbutane
 3-ethyl-2-methylhexane
Common Name
 The number of carbons in the alkane determines the
name
 all alkanes with four carbons are butanes, those with five
carbons are pentanes, etc.
 iso- indicates the chain terminates in -CH(CH3)2 , neo- that
it terminates in -C(CH3)3
CH3
CH3 CH2 CH2 CH3 CH3 CHCH3
Butane Isobutane

CH3 CH3
CH3 CH2 CH2 CH2 CH3 CH3 CH2 CHCH3 CH3 CCH3
CH3
Pentane Isopentane Neopentane
Classification of C & H
 Primary (1°) C: a carbon bonded to one other carbon
 1° H: a hydrogen bonded to a 1° carbon
 Secondary (2°) C: a carbon bonded to two other carbons
 2° H: a hydrogen bonded to a 2° carbon
 Tertiary (3°) C: a carbon bonded to three other carbons
 3° H: a hydrogen bonded to a 3° carbon
 Quaternary (4°) C:
C a carbon bonded to four other carbons
Example:
 Designate each carbon of these compounds as
primary, secondary, tertiary, or quaternary:
Physical Properties of Alkanes
 Nonpolar
 Insoluble in water.
 Lower density than water.
 Low boiling and melting points.
 Gases with 1-4 carbon atoms
 methane, propane, butane
 Liquids with 5-17 carbon atoms
 kerosene, diesel, and jet fuels:
 Solids with 18 or more carbon atoms
 wax, paraffin, Vaseline
Chemical reactions of Alkanes
 Combustion:
 Alkanes react with oxygen.
 CO2, H2O, and energy are
produced.
 Alkane + O2  CO2 + H2O +
heat
 CH4 + 2O2  CO2 + 2H2O +
energy
  Halogenation:
 Alkanes react with Halogens.

heat or light
CH4 + Cl2 CH3Cl + CH2Cl2 + CHCl3 + CCl4

=>
Properties Of Alkane
Boiling point Melting point Density [g·cm3]
Alkane Formula
[°C] [°C] (at 20°C)
Methane CH4 -162 -183 gas
Ethane C2H6 -89 -182 gas
Propane C3H8 -42 -188 gas
Butane C4H10 0 -138 gas
Pentane C5H12 36 -130 0.626(liquid)
Hexane C6H14 69 -95 0.659(liquid)
Heptane C7H16 98 -91 0.684(liquid)
Octane C8H18 126 -57 0.703(liquid)
Nonane C9H20 151 -54 0.718(liquid)
Decane C10H22 174 -30 0.730(liquid)
Undecane C11H24 196 -26 0.740(liquid)
Dodecane C12H26 216 -10 0.749(liquid)
Icosane C20H42 343 37 solid
Triacontane C30H62 450 66 solid
Source of Alkanes
 Natural gas
 90 to 95 percent methane
 5 to 10 percent ethane, and
 a mixture of other low-boiling alkanes, chiefly propane, butane,
and 2-methylpropane.
 Petroleum
 A thick liquid mixture of thousands of compounds, most of them
hydrocarbons formed from the decomposition of marine plants
and animals.
Cycloalkanes
 General formula CnH2n
 five- and six-membered rings are the most common
 Structure and nomenclature
 to name, prefix the name of the corresponding open-chain
alkane with cyclo-, and name each substituent on the ring
 if only one substituent, no need to give it a number
 if two substituents, number from the substituent of lower
alphabetical order
 if three or more substituents, number to give them the
lowest set of numbers and then list substituents in
alphabetical order
THANK YOU....
HOME WORK
1
 Provide IUPAC names for these alkanes:
2
 Draw condensed structural formulas or line
drawings for each of the following compounds:
 3-ethylpentane
 2,2-dimethylbutane
 3-ethyl-2-methylhexane
 4-isopropyloctane
 6-sec-butyl-7-ethyl-2,2,5,8-tetramethylnonane
3
 The following names have been assigned
incorrectly. Draw the structure corresponding to the
name, and assign the correct IUPAC name.
 3-sec-butylpentane
 2-ethyl-2,6-dimethylhexane