HYDROCARBON

COMPOUNDS
Intended Learning Outcomes
The students should be able to:
1. Identify the type of organic
compound
2. Name the organic compound
3. Write the structural formula of
organic compound
 HYDROCARBON
 an organic compound made up of
Carbon and Hydrogen
 naturally-occurring compounds and
form the basis of crude oil, natural
gas, coal, and other important energy
sources

3
 Hydrocarbons
at Room Temperature

0 Gas  Liquid  Waxy 0 Plastic

0 Methane 20 to 40 40 or more
0 Ethane 5 to 19 Carbons Carbons
0 Propane Carbons
0 Butane
 Melting Point
0 As the length of hydrocarbons get longer, the Melting
Point grows Higher.

Melting and Boiling Temperatures of Alkanes

600

500

400

300 Boiling Point (˚C)

Tempurature (˚C)

200 Melting Point(˚C)

100

-100

-200

-300
0 5 10 15 20 25 30 35 40 45
Number of Carbons
6
 Alkanes
0 obtained from the fossil fuel
resource
0 derivatives are used in
hundreds of products such as
plastics, paints, and other
materials
0 Some alkanes are highly combustible and
are valuable as clean fuels, burning to
form water and carbon dioxide.
0 Methane, ethane, propane and butane are
gases and used directly as fuels.
0 Alkanes from pentane up to around C17H36
are liquids.
 ALKANES
0 Hydrocarbons which contain only single
bonds are called alkanes (paraffins).
0 They are called saturated hydrocarbons
because there is a hydrogen in every
possible location.
0 This gives them a general formula CnH2n+2
Carbon and Hydrogen
 Alkanes
0Saturated hydrocarbons
0Each carbon bonded to four
other atoms

CH4

n- number of carbon

CnH2n+2 12
 Molecular Formula of Alkane
0 Write the molecular formula of alkane with:

1. 2 carbons C2H6

2. 3 carbons _________________

3. 6 carbons _________________

4. 8 carbons _________________
Structural Formula
 Alkanes
H H H H H H H H H H H H H H H
H C H H C C H H C C C H H C C C C H H C C C C C H
H H H H H H H H H H H H H H H

methane ethane propane butane pentane

CH3 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3
 Naming simple Alkane
0 Use prefix that will indicate the number of C
atoms
0 The name of alkane ends with –ane

Examples:
CH4 methane
C4H10 butane
Skeletal Structure of Alkane
UNSATURATED
HYDROCARBON

20
Classes of Unsaturated Hydrocarbons
0 1. Alkenes – An acyclic hydrocarbon
with one or more carbon-carbon
double bonds
(with one double bond : CnH2n )
0 2. Alkynes – An acyclic hydrocarbon
with one or more carbon-carbon triple
bonds (with one triple bond : CnH2n-2 )
0 3. Aromatic – A cyclic hydrocarbon
six*-carbon (usually) ring containing
three carbon-carbon double bonds.
* known as a benzene ring (C6H6).
 UNSATURATED
HYDROCARBONS
Alkenes (Olefins)
0Contains double bond
0General formula: CnH2n
0End in ene
 ALKENES
0 Double bond – ethylene or ethene - CnH2n

H H
C C
H H

23
 Alkenes
0 An alkene can be formed by removing a
hydrogen atom from two adjacent
carbons in a carbon chain.
0 Ex: Hexane -C—C—C—C—C—C-
becomes
0 Hexene -C—C—C=C—C—C-
(3-Hexene)

0 Ex: Ethane -C-C- becomes

0 Ethene -C=C-
(also known as ethylene)
 ALKYNES (Acetylenes)
0General Formula: (CnH2n-2)
0Aliphatic hydrocarbons with one
triple bond between carbons are
called alkynes.
0They follow the naming convention
of the alkanes except that the suffix
-yne is used instead of -ane.
 ALKYNES
0Alkynes are unsaturated
hydrocarbons and are generally
very reactive.
0Typical reactions involve the
addition of hydrogens or
halogens.
 Alkynes
0 Formation is similar to that of alkenes (more
hydrogens are removed; higher temp.)
0 Ethyne = Acetylene
0 Naming: same rules as for alkenes
0 Properties & Reactions are similar to those of
alkenes
Unsaturated Hydrocarbons
0 Triple bond – acetylene or ethyne - C H
n 2n-2

H C C H

28
 Ethyne
0 The simplest of the alkynes series, it is
commonly called acetylene.
0 It is often used as a fuel for welding
torches since it produces a large amount
of heat upon combustion.
0 Oxyacetylene welding uses compressed
acetylene and compressed oxygen for
mixing in the torch flame.
 Aromatic Hydrocarbons
0 An aromatic hydrocarbon
(abbreviated as AH) or arene is a
hydrocarbon, of which the molecular
structure incorporates one or more
planar sets of six carbon atoms that are
connected by delocalised electrons
numbering the same as if they consisted
of alternating single and double covalent
bonds 30
 Aromatic Hydrocarbons
0 Have ring structure with multiple bonds.
0 Benzene (C6H6) is the simplest aromatic.

H
H C H
C C
C C
H C H
H
Unsaturated Hydrocarbons
0 Benzene, C6H6, is the simplest and first recognized
aromatic hydrocarbon

32
0Nomeclature of Organic Compounds
Alkanes - Nomenclature

The name of every organic molecule has 3 parts:

1. The parent name indicates the number of carbons in
the longest continuous chain.
2. The suffix indicates what functional group is present.
3. The prefix tells us the identity, location, and number
of substituents attached to the carbon chain.
 Hydrocarbons
ex: Alkanes
0 1 – Meth-
0 2 – Eth-
0 3 – Prop-
0 4 – But-
0 5 – Pent-
0 6 – Hex-
0 7 – Hept-
0 8 – Oct-
0 9 – Non-
0 10 – Dec-
0 11 – Undec-
0 12 – Dodec-
Alkanes - Nomenclature

Parent – Longest straight carbon chain

Alkanes - Nomenclature

Suffix – Our first functional group is alkane, so the suffix is –ane

For later functional groups we will drop the –ane root suffix for others
Alkane chain # Carbons Name
CH4 1 methane
CH3CH3 2 ethane
CH3CH2CH3 3 propane
CH3CH2CH2CH3 4 butane
CH3CH2CH2CH2CH3 5 pentane
CH3CH2CH2CH2CH2CH3 6 hexane
CH3CH2CH2CH2CH2CH2CH3 7 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 8 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 9 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 10 decane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 11 undecane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 12 dodecane
Alkanes - Nomenclature

Prefix – Our substituents will be branches in the alkane structure

A branch is another alkane minus one hydrogen – an alkyl group
Example – if CH3- is a branch on a longer chain:

CH3- is CH4 minus 1 hydrogen

Since it is a side chain it will replace the –ane suffix with –yl

CH3- is a methyl group

We can also abbreviate this group as Me-

Alkanes - Nomenclature

Prefixes -
Alkyl group Structure IUPAC name Abbreviation

CH3- CH3- methyl Me-

CH3CH2- ethyl Et-

CH3CH2CH2- n-propyl n-Pr

CH3CHCH3 isopropyl or i-propyl i-Pr

CH3CH2CH2CH2- n-butyl n-Bu

CH3CH2CHCH3 sec-butyl s-Bu

(CH3)2CHCH2- isobutyl or i-butyl i-Bu

(CH3)3C- tert-butyl or t-butyl t-Bu

C6H5- phenyl Ph
Alkanes - Nomenclature

1. Find the parent carbon chain and add the suffix.

Note that it does not matter if the chain is straight or it bends.

Alkanes - Nomenclature

Also note that if there are two chains of equal length, pick the
chain with more substituents. In the following example, two
different chains in the same alkane have seven C atoms. We
circle the longest continuous chain as shown in the diagram
on the left, since this results in the greater number of
substituents.
Alkanes - Nomenclature

2. Number the atoms in the carbon chain to give the first

substituent the lowest number.
Alkanes - Nomenclature

If the first substituent is the same distance from both ends,

number the chain to give the second substituent the lower
number.
Alkanes - Nomenclature

When numbering a carbon chain results in the same numbers

from either end of the chain, assign the lower number
alphabetically to the first substituent.
Alkanes - Nomenclature

3. Name and number the substituents.

• Name the substituents as alkyl groups.
• Every carbon belongs to either the longest chain or a
substituent, not both.
• Each substituent needs its own number
• If two or more identical substituents are bonded to the
longest chain, use prefixes to indicate how many: di- for two
groups, tri- for three groups, tetra- for four groups, and so
forth.
Alkanes - Nomenclature

4. Combine substituent names and numbers + parent and suffix.

• Precede the name of the parent by the names of the substituents.
• Alphabetize the names of the substituents, ignoring all prefixes
except iso, as in isopropyl and isobutyl.
• Precede the name of each substituent by the number that indicates
its location.
• Separate numbers by commas and separate numbers from letters
by hyphens. The name of an alkane is a single word, with no
spaces after hyphens and commas.
Structural Isomer

 a type of isomer in which

molecules with the same
molecular formula have different
bonding patterns and atomic
organization
• Hexane is an straight-chain alkane with six carbon atoms
and has the molecular formula C6H14. Hexane is a
significant constituent of gasoline. It is a colorless liquid,
odorless when pure, and with boiling points approximately
69 °C. It is widely used as a cheap, relatively safe, largely
unreactive, and easily evaporated non-polar solvent.

• Isomers of hexane
 Functional Groups
0 The atom or group of atoms that replaces
hydrogen atoms from hydrocarbon
0 They may be –OH, -COOH, -CO, -CHO, -Cl, -
COCl, -COOR etc.
0 Functional groups are responsible for the
characteristics and reactivity of a molecule.
0 Different functional groups give rise to
different reaction types in organic chemistry
 Alcohol and phenol
0 Alcohols are compounds in which the hydroxyl group
(-OH) is linked to aliphatic carbon chain or in the side
chain of an organic compound.
0 Phenols are compounds containing a hydroxyl group
attached to an aromatic ring.
Tests for Functional Groups
0Bromine test
0Ceric ammonium nitrate test
0Sodium Bicarbonate test
 Bromine Test
0 a qualitative test for the presence of unsaturation
(carbon-to-carbon double or triple bonds),
0 An unknown sample is treated with a small amount of
elemental bromine in an organic solvent,
0 Presence of unsaturation in the sample is shown by
disappearance of the deep brown coloration of
bromine when it has reacted with the unknown
sample
Bromine Test
 Ceric ammonium nitrate test
• Test for alcoholic group
• Alcohols reacts with ceric ammonium nitrate to form a red
coloured alkoxy cerium (IV) compound.
Sodium bicarbonate test
0 When carboxylic acid reacts with sodium
bicarbonate solution carbon dioxide is
evolved with a brisk effervescence along
with sodium acetate is formed.

0 The chemical reaction is given below.

RCOOH + NaHCO3 → RCOONa + H2O + CO2↑
(brisk effervescence)

0 This test is used to distinguish between

carboxylic acid from phenol. Phenol does
not answer to this test.
 Materials for Labster simulation

Test tubes with rack

Micropipette tips

Micropipette

Vortex mixer beaker

 References:
0 Brown,B.S, Holme,T.A,(2012) Chemistry for Engineering Students,
2ed: Cengage Learning Asia Pte Ltd
0 Chang, R. (2010). Chemistry. Boston: McGraw-Hill Higher Education.
0 Masterton,W.L, et al (2018) Principles and Reactions: Chemistry for
Engineering Students, Cengage Learning
0 Tests for functional groups. Extracted from:
http://www.amrita.olabs.edu.in/
Thank you!
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