Form four note book chemistry

CHAPTER 3: Organic Chemistry

Organic chemistry: is the study of compounds carbon and hydrogen
: is the study of hydrocarbons
Carbon: is a non-metal in Group IV (5) of the periodic table
: it forms covalent compounds.
there are three special features of covalent bonding involving carbon

1. Carbon atoms can join to each other to form long chains

2. Carbon atoms in a chain can be linked by single, double or triple covalent bonds
3.Carbon atoms can also arrange themselves in rings
Hydrocarbons
Hydrocarbons: is a compound contain hydrogen and carbon only.
Hydrocarbons

Aliphatic Aromatics
(carbon attached straight chain) (carbon attached ring )
Don’t contain benzene group or benzene ring (contain benzene group or benzene ring)

Saturated Unsaturated
(single bond) (double or triple bond)

Alkanes cyclokanes Alkenes alkynes

Aliphatic

Cyclic Acyclic
(ring structure with closed chains) (straight chain or branched chain with open chains )
(Alkanes, alkenes &alkynes)

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Types of formulae and Models
Formula

Empirical formula Molecular formula

:is a formula that shows the simples whole number :is the formula which shows the number of
ratio of the atoms of each element present in compound atoms of each element present in one molecule
Example of the substance
What is the empirical formula o ethane? Example:
2.4g of carbon and 0.69 of hydrogen Empirical formula CH3 RMM 30
CH3 find molecular formula? C2H6
Models

A ball and stick model Space-filling models

(shows atoms as balls and bonds as sticks) are accurately scaled-up image of the molecule
but bonds are not shown

Other Formula

Displayed Formula Structural formula Skeletal formula

:is a formula shows every atom :is a formula shows the unique :is a formula shows the carbon
and every bond in a molecule arrangement of atoms in a skeleton only.
- single bond molecule in a simplified from E.g. hexane
double bond without showing all the bonds

triple bond
E.g. ethane C2H4 E.g. hexane
CH3CH2CH2CH2CH2CH3

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 Isomerism
Isomer: are compound same formula but different structure.
Isomerism
Structural Isomerism Stereoisomerism

positional Functional Chain geometric optical

Isomerism Isomerism Isomerism Isomerism Isomerism

1) Structural isomerism
:are molecules with the same molecular formula but with different structural arrangement of atoms.
Example: Structural isomers of butane C4H10

A) Positional Isomerism:
the functional group is attached to the chain at different points, this is called positional isomerism.
Example: the molecular formula C3H7 CL could represent
CH3CH2CH2CL CH3CH2CLCH3
1- Choloropropane 2- Cholorpropane
B) Functional group Isomerism:
there are different groups. Example: the molecular formula C2H6O could represent

C) Chain Isomerism
the hydrocarbon chain is arranged differently Example: the molecular formula C4H9OH could represent.

2) Stereoisomerism
A) geometric isomerism (cis-trans isomers)
occurs in alkenes when both carbon atoms forming the double bond are attached to two different groups.

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Nomenclature of organic compounds
the system of naming organic compounds is based on the rules establish by the IUPAC, International Union
Pure Applied Chemistry.
Alkanes
 Is hydrocarbons with only single bonds.
 Are aliphatic saturated hydrocarbons between two carbons atoms contain single bond
 Are the simplest type of hydrocarbons
 Have a general formula CnH2n+2
 The functional group of alkanes is (ane)
 Alkanes are named by using stem + suffix (ane)
Alkyl groups
 Alkyl groups are saturated hydrocarbon radicals having the general formula
 Alkyl groups are derived from alkanes by removing a single hydrogen atom and also their names are
derived by changing the suffix-ane of alkanes to –yl

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Note: the groups attached to the any carbon atom in the parent structure are called side group, side chains
or substituents.
di- 2
tri- 3
tetra- 4
Example: most side chains include, methyl , ethyl, Cl, Br, I and F

Example:
Find out the structural formula of
methane propane hexane ethane butane and heptane?

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 Example1:
work out naming with IUPAC with these hydrocarbons

H H H H H H H H H H CH3 H H H

H–C–C–C–C–C–C–C-H H–C–C–C–C–C–C–C-H

H H H CH3 H H H H CH3 H CH3 H H H

H H H H H

H–C–C–C–C–C-H

H Br H Br H

H H H H H CH3 H CH3 H

H–C–C–C–C–H H–C–C–C–C–C-H

H H Br H H CH3 H H H

H H H H Cl CH3 H H H H H H Cl CH3 H H

H–C–C–C–C–C–C–C–C- H H–C–C–C–C–C–C–C–C- H

H Br H H H H H H H H H H H H H H

H H I H H H H H H CH3

H–C–C–C–C–C-H H–C–C– C–C–C-H

H Br H H H H Cl H Br CH3

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Example 2:

CH3 – CH – CH3 CH3 – CH – CH3

CH3 CH2 - CH3

CH3 – CH2 – CH2 – CH - CH2 - CH2 - CH3 CH2 - CH3

CH3 – CH2 – CH2 – CH - CH2 - CH2 - CH3

CH2 - CH3

CH3

CH2 - CH2 - CH3 CH3

CH3 – CH2 – CH - CH2 – CH - CH2 - CH2 - CH3 CH3 – CH2 – C - CH2 – CH - CH2 - CH3

CH3 CH3 CH3

CH3 CH3 CH3

CH3 – CH2 – C – CH3 CH3 – C – CH2 – CH2– CH – CH3

CH3 CH3 Cl

CH2 – CH3 CH3

CH3 – CH2 – C – CH2 – CH3 CH3 – CH – C - CH2 – CH - CH2 - CH3

CH2 – CH3 Br Cl CH3

H H CH3 CH3

Cl – C– C – H CH3 – CH2 – C – CH – CH – CH3

Cl H CH3 Cl

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 Example3:
Draw the structural formula for the following molecules.

4-ethyl-octane 2-methyl-nonane 3,3-dicholoro-pentane

3-ethyl-pentane 3-ethyl-2methyl-heptane 2,2,3-trimethyl-butane

3-ethyl-2,2-dimethyl-hexane 4-ethyloctane 2-methylnonane

3-choloropentane 3-Borom -2-methylheptane 2,2,3-trimethylbutane

3-ethyl-2,2-dimethylhexane 4-ethyl-octane 2-boromo-3-choloro-butane

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 Alkene
 A hydrocarbon that contains at least one C C bond is called an Alkene.
 with two H atoms removed to make the double bond.
 Alkenes have the general formula CnH2n
 Alkenes are considered Unsaturated hydrocarbons.
 The functional group of alkanes is (ene)

Naming alkenes
Example:

H H H H H H H H H

H – C – C – 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 H H H H H H

H – C – C – C – C – C – C- C - H H – C – C – C – C – C – C – C – C- H

H H H H H H H H

H H H H H H H H CH3 H H C2H5 H H H

Br – C – C – C – C – C – C- C - H C–C –C–C–C–C–C– C–C–C-H

H CH3 H H H H H CH3 H H H H H H

H Cl H H H H Br H H CH3

Cl – C – C – C – C – C – C- C - H H–C–C–C–C–C–H

H CH3 H H H H Cl H H H

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 Alkynes:
 Hydrocarbons that contain at least one C C bond are called alkynes.
 The general formula of alkynes are CnH2n-2
 Alkenes and alkyes are much more reactive than alkanes
Alcohols
 the alcohol functional group consists of a carbon bonded to an – OH,
 the general formula of an alcohol is R-OH (or CnH2n+1 OH)
 simple alcohols are named by dropping the final – e from the parent hydrocarbon name and adding the suffix
– ol
 the physical properties of the smaller alcohols are similar to those of water, they have high melting and
boiling points as a result of hydrogen bonding, and they dissolve polar molecules and some salts.
Classification of alcohols
depending on the number of hydroxyl groups they contain, alcohols are generally classification as follows

alcohols

Monohydric alcohols Polyhydric alcohols

contain only one hydroxyl group (- OH) contain two or more hydroxyl groups

Dihydric alcohols Trihydric alcohols

contain two hydroxyl groups contain three hydroxyl groups

H H H H H
H C– C-H H C – C – C – OH

OH OH OH 0H 0H
ethan 1,2 diol propan 1,2,3-triol

Primary alcohols Secondary alcohols Tertiary alcohols

are those in which the carbon attached are those in which the carbon are those in which the carbon
to the OH is attached 1 other carbon atom attached to the OH is attached to atom attached to the OH is attached to 3 other
or functional group is at the end of the 2 other carbon atoms or functional carbon atoms or functional group is attached to
chain group is not at the end of the chain to a carbon which also has a branch attached to it
Example Example Example
H H H H OH H H OH H

H – C– C – C – OH H–C–C–C–H H C– C–C–H

H H H H H H H CH3 H
propanol propan – 2-ol 2- methylpropan – 2-ol

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Naming of Alcohol
give systemic name with these compounds.

H H H OH H H H H H H CH3 OH H H H H

H C–C–C–C–C–C–C–C–H H C–C–C–C–C–C–C–C–H

H H H H H H H H H H H H H H H H

H H H OH H OH H OH

H C–C–C–C– H H C–C–C–C– H

H H H CH3 H H H CH3

H H H H H H H H H H

H C–C–C–C– C- H H C–C–C–C– C- H

H H OH CH3 H H H OH H H

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Part 2: Reaction mechanisms
organic reactions are classified three important classes according to the chemical process involved.
Organic reactions:

Additional reaction Elimination reaction Substitution reaction

occurs when an unsaturated reactant occurs when a saturated reactant occurs when an atom (or group)
becomes a saturated product. becomes an unsaturated product. from an added reactant substitutes
for one in the organic reactant.

Types of bond fission

the breaking of a covalent bond is called bond fission.
reactions of organic compounds involve bond fission followed by the formation of new bonds.

Bond fission

Homolytic fission Heterolytic fission

bond breaking produces two species bond breaking produces two species
of the same (homo-) type. of different (hetero-) type.
A:B A + B (free radicals) A:B A + B ions or A: B A + B ions
Free radicals: is a species which contain an unpaired

Electrophiles nucleophiles
positive ions + negative ions -
is an electron – deficient species is an electron – rich species

Important Terminology:

Initiation: is the production of free radicals by hemolytic fission of a covalent bond.

Propagation: is the reaction of a free radical with a molecule to produce another free radical.
Termination: is the combination of two free radicals to form a single molecule.
Substitution reaction: is one in which one atom or group of atoms on the organic molecule is directly
replaced.

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 Part 3: Polymers
 Polymers are large organic macromolecules. Poly= many and Mer= unit (many units)
 They are made up of many (sometimes thousands of) small molecules joined together in a chain.
 The small molecules making up the chain are called monomers.
 The chain is called the polymer.
 The chemical reaction in which monomers combine to form a polymer is called polymerization.
 Macromolecules or large molecules are common in living things.
E.g. natural polymers (starch, proteins, wood and natural rubber found in plants and animals)
E.g. Synthetic or man-made (often called plastics)

Polymers

Homopolymers Copolymers
containing just one type of monomer. are made up two or different types of monomers
For example: Poly (ethen), poly (propene) for example: nylon
and poly (chloroethene). Nylon: is made from two monomers and
biological proteins are made from 20 different monomers, amino acids

Monomer: ethene

H H H H H H H H H H

C– C C– C C– C C– C C– C

H H H H H H H H H H

Double bonds break open

H H H H H H H H H H

C– C- C– C- C– C- C–C- C– C-

H H H H H H H H H H

Polymer: polythene

H H H H H H H H H H

H–C–C–C–C–C–C–C–C- C–C–H

H H H H H H H H H H

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 Poly (ethene) is produced in two main forms.

1. low density poly (ethene) (LDPE) (The chains branch as they form)
2. High density poly (ethene) (HDPE) (form long straight chains )

poly (ethene) has many useful properties

 It is easily moulded
 It is an excellent electrical insulator
 It does not corrode
 It is tough
 It is not affected by the weather
 It is durable
Some examples of polymers

Polymer (and trade- Monomer Properties Uses

names)
Poly (ethene) ethene Tough, durable Plastic bags, bowls, bottles,
(polyethylene) CH2 CH2 packaging
(polythene)
Poly (propene) propene Tough, durable Plastic ropes, packaging
(polypropylene, PP) CH3 CH CH2

Poly (colorethene) chloroethene Strong, hard (not as Electrical insulation, pipes and
(polyvinyl chloride, CH2 CHCl flexible as polythene) guttering
PVC)
Poly (tetraflouroethene) tetraflouroethene Non-stick surface, Non-stick frying pans, non-stick
(polytetrafluoroethylene, CF2 CF2 withstands high taps and joints
teflon, PTFE) temperatures
Poly (phenylethene) phenylethene Light, poor conductor Insulation, packaging (foam)
(Polystyrene, PS) C6H5CH CH2 of heat.

Making nylon:
Nylon is a copolymer of the monomers hexanediodic acid (a six carbon organic acid with a carboxyl group;
-COOH at each end)

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 Part 4: Haloalkanes:
alkane combine with Halogens to form Halogenalkane
example:
1-bromomethane 1,3 - diidohexane
H H H H H H H
H–C –H H–C–C–C–C–C–C-H
Br I H I H H H

Haloalkanes

Primary halogenoalkane Secondary halogenoalkane Tertiary halogenoalkanes

carbon atom is bonded to carbon atom is bonded to carbon atom is bonded to
one another carbon atom two another carbon atom three another carbon atom.
Example: 1- cholorobutane Example: 2- cholorobutane Example: 3- cholorobutane
H H H H H H H H H H H H
H–C–C–C–C–H H- C – C – C – C – H H-C–C–C–C–H
Cl H H H H Cl H H H H Cl H

Uses of halogenoalkanes:

 Synthesis of medicine such as ibuprofen

 Direct application for plastics like poly (chloroethene)
 Production of aerosols and foams.
 Waterproof clothing like poly (tetraflouroethene)

End of chapter 3

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