Introduction to Science

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Week 7: Lesson 1
Introduction to organic chemistry

This week you will learn how to:

• Distinguish between classes of hydrocarbons.
• Determine the molecular and structural formulas of hydrocarbons.
• Draw the skeletal and condensed structural formulas of hydrocarbons.
• Demonstrate knowledge of the nomenclature of hydrocarbons.
Organic Compounds

What is Organic chemistry?

Organic chemistry is a branch of chemistry that studies carbon containing compounds.

The carbon atom is a special element, which makes abundant and diverse molecules
from covalent bonds. Living organisms are principally made of carbon containing
molecules called organic compounds. The organic chemistry study encompasses the
study of the structure, properties, composition, synthesis and reaction of organic
molecules.
Organic Compounds

Diversity of organic compounds

• There are less than 300 000 inorganic compounds exist despite numerous
inorganic elements in the environment, whereas more than 13 million organic
compounds (100 000 newly discovered molecules annually) were currently found
and made of few elements, mostly (C, H, O, N…)

• More than 95% of matter – made up of organic compounds:

• Organic compounds are found in food stuff, fuel, medicine, plastics & s o m e
polymers, toiletries, cosmetics, dyes & colorants, flavourants & additives, human
tissue & other biological tissue, etc.
Organic Compounds
What causes the diversity of organic compounds?

The carbon atom has 4 valences

Different bonding sequences (single, double and triple bond)
Bonding arrangements
Types of atoms in structure
Number of carbon atoms
Functional groups in structure
Isomers (constitutional Isomers)
Alkane: CnH2n+2, Example?
Alkene: CnH2n
Alkyne: CnH2n-2
Organic Compounds

What is Functional group

A functional group is a group of atoms bonded together within the molecule, which
displays specific properties. It is the center of reactivity in an organic molecule (e.g.
alkene???).

Properties of some functional groups stronger than others. This make functional
group to be classified according to the highest priority in structure, specially when it
comes to naming multifunctional organic compounds (suffix).

Carboxylic acid > Anhydride > Ester > Acid halide > Amide> Nitrile >
Aldehyde > Ketone > Alcohol > Amine > Alkene > Alkyne > Alkane
Organic Compounds
Organic Compounds

Introduction to hydrocarbons
Saturated hydrocarbons generally are known to be unreactive compounds.
However, they are prompt to combustion and radical reaction. Unsaturated
hydrocarbons are more reactive because of the presence of double or triple
bonds of which the pi bond is easily breakable. Most of the reactions are
addition reactions.
Organic Compounds

Introduction to hydrocarbons
The structure of hydrocarbons contains the carbon and
hydrogen atoms only. They can be divided into subgroups.
Organic Compounds

Basic hydrocarbons
Organic Compounds
Types of Organic Formulae
Organic molecules are represented using different types of
formulas. The following diagram demonstrates the difference
between the formulas:
Organic Compounds

Alkyl group
Removing a hydrogen atom from an alkane gives a structure called alkyl
group. Alkyl groups are named by replacing the –ane of alkane with an –yl
(Methyl, ethyl, propyl, butyl and pentyl…). n-Alkyl groups are formed by
removing a hydrogen from main end carbon. Branched alkyl groups are
formed by removing a hydrogen from an internal carbon. (Primary or second
carbon).
Organic Compounds

The most common alkyl

substituents and branched
substituents are summarised
in the table:
Organic Compounds
Nomenclature (IUPAC)
Nomenclature refers to naming of compounds. Naming organic compounds follows numbers of
roles.
Compounds are classified according to the highest priority functional group.
Parent chain – longest continuous carbon chain with highest priority functional group in it.
Substituent – carbon (alkyl) atoms or other functional groups attached to parent chain.
Family name – name ends with suffix of highest priority functional group
• Identify the functional group of highest priority. The name ends with the suffix of the family
name (ol for alcohol)
• Identify the longest continuous carbon chain as the parent chain (There are 5 carbon atoms =
pentane)
• Number the parent chain from the functional group of highest priority.
• Identify the substituents attached to the parent chain (methyl)
• Indicate the position of the functional group of highest priority. (1 – ol)
• Indicate the position of the substituents (3 – methyl)
• When naming, place the substituents first in alphabetical order followed by the parent chain
and end
with the family name (3 – methypentan – 1 – ol)
Common Names
Organic Compounds
Organic Compounds

Nomenclature (IUPAC)
Organic Compounds

What are hydrocarbons and alkyl halides?

• Hydrocarbons are organic compounds containing carbon and hydrogen
atoms only. These atoms in hydrocarbons are bonded by covalent bonds.
There are three classes of hydrocarbons: alkanes, alkenes and alkynes.
Alkanes are hydrocarbons in which carbon atoms are bonded to each other
with single covalent bonds. Alkenes have at least one double bond, whereas
alkynes have at least one triple bond. A double bond contains a strong and
hard to break sigma (σ) bond and weak and easily breakable pi (π) bond.
Hydrocarbon can be open chains (aliphatic or acyclic) or cyclic.

• Alkyl halides also called haloalkanes are organic compounds that derive
from alkanes from the replacement of one or more hydrogen atoms of the
alkane by halogen atoms (F, Cl, Br, I).
Organic Compounds
Chemical properties
Alkanes are saturated (contain single bonds only) hydrocarbons (they
contain hydrogen and carbon atoms only).
Aliphatic or acyclic alkanes are open chains.

Cyclic alkanes form rings of carbon atoms

Alkanes (also called paraffins) are generally not very reactive

compounds. However, they undergo combustion reaction by reacting
with oxygen to produce carbon dioxide (CO2) and water (H2O).
Alkane can react with halogens, in substitution reactions, in presence
of UV light or heat.
Organic Compounds

Physical properties of alkanes

Alkanes containing one to two atoms of carbon are gases eg.

natural earth gas (methane & ethane) & LPG (Liquefied Petroleum
Gas: propane + butane). Alkanes containing 5 to 17 atoms of
carbon are liquid. eg. mineral oil used in food stuff, cosmetics,
lubricants, petrol. Between 18 and 29 atoms of carbon paraffins
are soft and hard when they contain more than 29 carbon atoms
(wax e.g candles)
Organic Compounds

Nomenclature

1. Find the longest carbon chain and name it.

2. Number the chain to give the substituents the

lowest number possible

3. Identify and name the substituent

4. Arrange the substituents alphabetically

Organic Compounds
Nomenclature of alkanes

Functional group (Single bond between carbon atoms)

General formula for aliphatic alkanes
CnH(2n + 2)
Family name: “ane”
How to name aliphatic alkanes
Select the longest continuous carbon chain. This chain determines the base name or parent name for the structure.
Number chain from side closest to a highest priority substituent or the first point of difference
Identify and number the substituents on chain
Name the structure using hyphens (one word) in the following order: substituent-parent chain-family name
When two or more substituents present, list them in alphabetical order in name
Two substituents present on same carbon: Number each substituent.
Or 4-isopropyl-4-methylheptane or 4-methyl-4-(1-methylethyl)heptane
Two or more same substituents present:
Use the prefixes di (2); tri (3); tetra (4) ...
Substituents present at equal lengths from either side – lowest number order
When there are More than one parent chain, choose one with most substituents
Organic Compounds

Nomenclature of alkanes
Organic Compounds

Nomenclature of Cycloalkanes

• Nomenclature of cycloalkanes follow that of alkanes with the prefix cyclo- before the base name.
• General molecular formula cyclic alkane
CnH2n
• Cyclo- structures represented as line structures Carbons are not shown in main structure.
• C-atom at intersection of two lines and at the end of a line.
• Hydrogens are not shown. All other atoms are shown
Substituents on cycloalkanes:
• Find the parent structure
• Start at point of attachment and number around the ring.
• Number the substituents and write the name.
• Two substituents – number in alphabetical order.
• More than 2 substituents –number from the point that will give the lowest set of numbers for
Organic Compounds

Nomenclature of Cycloalkanes
Organic Compounds

Name and draw the following compounds

Organic Compounds
Organic Compounds

Physical properties of alkenes

Alkenes are unsaturated hydrocarbons
They contain at least a carbon - carbon double bond.
Alkenes may be gas, liquids or solids depending on the number of carbon atoms in the structure. Alkenes of 1 to
4 carbon atoms are colourless gases, from 5 to 15 alkenes are liquids. When they contain more than 15 atoms of
carbon, alkenes are solids. Alkenes are non-polar and dissolve in organic solvent rather than water. The boiling
point of alkenes increase with the molecular mass.

Alkenes are more reactive than alkane because of presence of a double bond. They undergo various reactions
including combustion, addition, hydrogenation, and halogenation reactions.
Ethylene and propylene are the two most important industrially produced organic chemicals, used in plastic and
other polymer production. Produced by “cracking” C2-C8 alkanes upon heating to temperatures up to 900 oC.
Saturated hydrocarbons generally are known to be unreactive compounds. However, they are prompt to
combustion and radical reaction. Unsaturated hydrocarbons are more reactive because of the presence of
double or triple bonds of which the pi bond is easily breakable. Most of the reactions are addition reactions.
Organic Compounds
Organic Compounds
Nomenclature of alkenes

Functional group
double bond between C atoms
General molecular formula open chain:
CnH2n
General molecular formula cyclic alkene
CnH2n-2
Family name: ene
To name alkenes:
Select the longest continuous carbon chain with double bond in the chain.
Number from side closest to double bond.
Give position for double bond (lower number of the 2 carbons).
Change name of chain from ane to ene.
Number chain with substituents from side closest to double bond.
More than one double bond present: give position of each double bond and add prefix di, tri, tetra....
to ene, eg. diene, triene...
Organic Compounds
Nomenclature of cyclic alkenes

Number cycloalkene so double bond is between C1 and C2 and first substituent has lowest
number possible.
It is not necessary to specify the position of the double bond in the name as the bond is always
between C1 and C2, if it is the highest priority functional group
If there is more than 1 double bond, give the position of the first carbon of each double bond.
If there are substituents on cycloalkenes: Find the parent structure and start at double bond
(C1=C2) and number in direction closest to substituent

Benzene: It has a 6-carbon ring with three alternating bonds

Also referred to as aromatic compound as most fragrances and flavours contain a benzene
ring.
Many natural occurring compounds are aromatic – eg. estrone and morphine. Many synthetic
drugs eg Prozac. Monosubstituted benzenes are systematically named with benzene as parent
name.
Organic Compounds
Organic Compounds

Physical properties of alkynes

Alkynes are unsaturated hydrocarbon with a triple bond between C atoms.

Higher degree of unsaturation than alkenes. Rare in nature, found in
components with antimicrobial& fungal properties in plants. Also used in
pharmaceuticals eg. contraceptives and active ingredient in the
antiretroviral Efavirenz (ARV for HIV treatment) . Most common alkyne:
acetylene (ethyne). Fuel for high temp flames eg. Welding flames (3300°C).
Polyacetylene plastics have conduction properties (useful in electronic
devices).
Organic Compounds
Nomenclature of alkynes
Functional group: Triple bond between C atoms

General molecular formula open chain: CnH2n-2

General molecular formula cyclic alkyne:

CnH2n-4

Family name: yne

Select the longest continuous carbon chain with a triple bond in the chain.

Number from side closest to triple bond

Give position for triple bond (lower number of the 2 carbons).

Change name of chain from ane to yne

Number chain with substituents from side closest to triple bond.

More than one triple bond present: give position of each triple bond and add prefix di, tri, tetra...., eg. diyne, triyne...
Organic Compounds

Nomenclature of Cyclo alkynes

Cycloalkynes are not common. The triple bond puts too much tension on the
structure, and it collapses. The smallest cycloalkyne is:

Alkynes

Parent chain containing both a double (en) and triple (yne) bond. The parent
chain is numbered from the side closest to a multiple bond.
Organic Compounds

Draw and name the following organic compounds

Organic Compounds

Alkyl halides properties

Haloalkanes (alkyl halides) – Compounds with a halogen atom bonded to a carbon atom. Commercially used
in: Halogenated polymers eg. PVC & Teflon, Solvents eg. chloroform & CCl4. Pharmaceuticals eg.
antidepressants, antimalarial, anesthetics

Other: flame retardants, fire extinguishers, refrigerants & fumigants

Some haloalkanes (eg. Chlorofluorocarbons) – pollutants leading to ozone depletion & greenhouse effects.

Functional group:

Halogen bonded to carbon

R-X where X = Cl, Br, F, I

Organic Compounds
General molecular formula open chain:

CnH2n+1X

General molecular formula cyclic alkyl halide:

CnH(2n-1)X

No family name → halide substituent: Cl (chloro), Br (bromo), F (fluoro), I (iodo)

Nomenclature of Alkyl Halides

Number the carbons of the parent chain beginning at the end nearer the first
substituent, whether alkyl or halo.
If there are 2 or more of the same substituents, use prefixes di (2), tri (3), tetra (4)
…before the part that is being repeated