CSEC Chemistry

Organic
Alkanes
9:05 am
 Organic Chemistry

1. Alkanes
2. Alkenes
3. Alcohols
4. Alkanoic Acids
5. Esters
6. Soaps & Detergents
7. Cracking

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 Group General Formula Functional Group Reactions Uses

Alkanes CnH2n+2 None Fuels (e.g., methane,

(single bonds only) Substitution Reactions propane, butane)
They can be cracked

Alkenes CnH2n C=C Plastics (e.g., polyethene),

(double bond) Addition reactions chemical feedstock

Alcohols CnH2n+1 -OH 1. Ethanol burns in air (oxygen) Solvents, fuels, and drinks
(hydroxyl group) 2. Ethanol reacts with sodium (ethanol)
3. Ethanol can be dehydrated
4. Ethanol can be oxidized
5. Ethanol reactions with Alkanoic Acids
to form Esters and Water

Alkanoic CnH2n+1COOH -COOH 1. Anhydrous Reactions Vinegar (ethanoic acid),

Acids (carboxyl group) 2. Aqueous Reactions preservatives
3. Reacts with alcohols to form esters

Esters CnH2n+1COOCxH2x+ -COO- Hydrolysis (acid or base), Perfumes, flavorings,

Formed from alcohol + carboxylic acid solvents
1

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 1 8

2 3 4 5 6 7

.What are the elements in Group 7 called? Halogens

How many valence electrons does Carbon have? 4

How many H will bond with a C atom? 4

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What is Bonding? - bonding is an attraction between atoms that hold them together

There are 3 types of bonding -

1. Ionic Bonding - between metals and non metals

2. Covalent Bonding - between nonmetals only
3. Metallic Bonding - between metals and other metals

Examples of molecules with covalent bonds are:

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Diatomic molecules

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 What are organic compounds
An organic compound is any member of a large class of chemical
compounds whose molecules contain carbon, with exception of
carbides, carbonates and carbon oxides.

e.g.
calcium carbide (CaC2),
silicon carbide (SiC)

Ok this is confusing, please give me

everyday examples of things that are
organic compounds or contain organic
compounds so I can related to it ! Jezzz

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Examples of everyday organic compounds
Asphalt
Mothballs
Candles
Nail polish & Remover
Coal
Natural gas
Detergent
Paint
Fabrics - nylon, polyester
Paper
Gasoline
Plastics
Alcohols
Rope
DNA
Soap
Proteins, Carbohydrates

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Types of Organic Compounds
1. Alkanes
2. Alkenes
3. Alcohols
4. Alkanoic Acids
5. Esters / Soaps / Detergents
6. Polymers
7. (Cracking) ← This is a process

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Alkanes

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Alkanes: CnH2n + 2 General formula

We can represent organic compounds 4 ways

1. Molecular Formula
2. Empirical Formula
3. Full structural Formula
4. Shortened Structural Formula

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Alkanes: CnH2n + 2

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Alkanes: CnH2n + 2

Pentane

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Alkanes: CnH2n + 2

Octane

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Alkanes: CnH2n + 2 1. Molecular Formula

2. Empirical Formulas

3. Shortened Structural Formula

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Naming branched Alkanes: CnH2n + 2

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Naming branched Alkanes: CnH2n + 2

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Naming branched Alkanes: CnH2n + 2

That branch has

2 Carbons

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 Sure it’s organic compounds that have the
same molecular formula but different structural
Hey Mr. Know-it-All can you tell
formulae.
me what an Isomer is?
This means sames amount of carbons and
hydrogens but they are arranged differently.

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 –C–C–C–C–C–

Ok so let’s see if I have this

right. Let’s draw and name
some isomers

Isomers are molecules with –C–C–C–C–C–

the same molecular
formulas, but different
arrangements of atoms.

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1. Alkanes burn in air or oxygen
2. Alkanes undergo substitution reactions
3. Alkanes can be cracked
Let’s look at the types of
reactions alkanes can undergo.

Also alkanes are call SATURATED

because they only contain single bonds

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1. Alkanes burn in air or oxygen

A clean, blue non-smoky flame is produced

Wow that’s really

clean and blue…
CH4 (g) + 2O2 (g) →CO2 (g) + 2H20(g) + ΔH -ve wooooo lala

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 H H

H C H + Cl Cl H C Cl + H Cl

H H

H Cl

H C Cl + Cl Cl H C Cl + H Cl

H H

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 2. Alkanes undergo substitution reactions
Chloromethane
CH4 (g) + Cl2 (g) →CH3Cl(g) + HCl(g)
Dichloromethane

Trichloromethane
CH3Cl(g) + Cl2 (g) →CH2Cl2(l) + HCl(g)
Tetrachloromethane

CH2Cl2(g) + Cl2 (g) →CHCl3(l) + HCl(g)

CHCl3(g) + Cl2 (g) →CCl4(l) + HCl(g)

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3. Alkanes can be cracked

Apply heat and pressure

What’s that
double bond thing
about?

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 More uses and properties of alkanes
Alkanes

1- 4 are gases
5 - 17 are liquids
States at Room Temperature
> 17 are solids
Pressure (RTP)
all alkanes are colorless and odorless

● Uses as fuels e.g. propane & ethane

● Methane can used to make hydrogen which is used to make ammonia
Uses ● Short chained alkanes such as hexane can be used as solvents to
remove grease.
● They can be cracked to produce alkenes

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Alkenes

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 General formula
Alkenes: CnH2n

Alkenes are a series of unsaturated

hydrocarbons containing a double bond.
Alkenes sound like
Alkanes

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Alkenes: CnH2n General formula

Naming Alkenes

Look for the

position of the
double bond

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Alkenes: CnH2n General formula

Naming Alkenes

Can you also draw

an isomer of this?

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Reactions of Alkenes

1. Alkenes burn in air or oxygen

2. Alkenes undergo addition reactions

1. Alkenes burn in air or oxygen

A yellow and smoky flame is produced

C2H4 (g) + 3O2 (g) → 2CO2 (g) + 2H2O(g) + ΔH -ve

The smoky flame is due to the unburnt carbon caused by the high proportion of
carbon to hydrogen atoms in alkenes 32
2. Alkanes undergo addition reactions

Because Alkenes can undergo

ADDITION reactions they can do
many cool things like…

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Hydrogenation - Addition of Hydrogen

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Halogenation- Addition of a Halogen

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Hydration - Addition of Water as Steam

Conditions: 300oC with Phosphoric acid (H3PO4) in silica catalyst at 60 atm

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Polymerisation - Linking Alkenes together

.....

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Alkane or Alkene? Hmmmm

Bromine Vapour

Acidified Potassium
Bromine Water
Manganate (VII) solution

To tell the difference we can do a test

using these 3 substances

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Alkane or Alkene? Hmmmm
Test Alkane Alkene

Slow decolorization of the bromine vapour in Rapid decolorization of the bromine vapour in
Add Bromine Vapour light (slow substitution reaction) light or dark (rapid addition reaction)

Rapid decolorization of the bromine water

Add Bromine Water No reaction - Hence no colour change
(rapid addition reaction)

Rapid decolorization of the potassium

Add Acidified Potassium
No reaction - Hence no colour change Manganate (VII) solution (rapid addition
Manganate (VII) solution reaction)

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 Uses and Properties of Alkanes & Alkenes
Alkanes Alkenes

2- 4 are gases
1- 4 are gases 5 - 15 are liquids
States at Room 5 - 17 are liquids > 15 are solids
Temperature > 17 are solids
Pressure (RTP) Alkenes are colourless and odourless
all alkanes are colorless and odorless with an exception of ethene which is a
colourless gas with pleasant smell.

● Uses as fuels e.g. propane & ethane

● Methane can used to make hydrogen
which is used to make ammonia
They are also used as the starting
● Short chained alkanes such as hexane
Uses materials of many other chemicals, such
can be used as solvents to remove
as alcohol, plastics and detergents.
grease.
● They can be cracked to produce
alkenes
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Alcohols

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 General formula
Alcohols: CnH2n + 1OH

Hi I’m Azul.
Let’s learn about
alcohols

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How can we make alcohols?

1. Fermentation

2. Hydration of Alkenes

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Fermentation

Yeast cells with

Carbon
Zymase
+ Glucose Ethanol + Dioxide
+ Energy
enzymes

This process was

known since 6000 BC
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Hydration - Addition of Water as Steam

I think we met this

earlier when we were
doing Alkenes 45
Reactions of Ethanol

1. Ethanol burns in air (oxygen)

2. Ethanol reacts with sodium
3. Ethanol can be dehydrated I never understood
4. Ethanol can be oxidized this in worm school
5. Ethanol reactions with Alkanoic
Acids to form Esters and Water

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Reactions of Ethanol

1. Ethanol burns in air (oxygen)

When ethanol is burnt in air, it burns with a clean blue flame, carbon dioxide and water are formed

C2H5OH(l) + 3O2 → 2CO2(g) + 3H20(g) H-ve

2. Ethanol reacts with sodium

When ethanol reacts with sodium metal it forms sodium ethoxide and hydrogen gas

2C2H5OH(l) + 2Na(s) → 2C2H5ONa(l) +H2(g)

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Reactions of Ethanol

3. Ethanol can be dehydrated

Ethanol can be dehydrated to give ethene by heating it with an excess of
concentrated sulphuric acid at about 170°C OR by passing ethanol vapour over
heated aluminum oxide.

C2H5OH(l) → C2H4(g) +H2O(l)

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Reactions of Ethanol
4. Ethanol can be oxidized by heating it with either acidified potassium permanganate
solution or acidified potassium dichromate solution to change into ethanoic acid.

C2H5OH(l) + 2[O] → CH3COOH(aq) +H2O(l)

potassium permanganate solution potassium dichromate solution

(good oxidizing agent) ((good oxidizing agent)
KMnO4 K2Cr2O7 49
 Uses of
alcohols

Used as fuels at they They can be used as

produce clean flames and solvents and hence used
They are used in alcohol
the reactions are in many chemicals such
beverages
exothermic. as perfumes and
varnishes

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 Alcohol
Abuse

Short Term Long Term

1. Slowed reflexes 1. Cirrhosis of the liver
2. Slurred speech 2. Aggravation of hypertension
3. Memory loss 3. Nervous disorders
4. Loss of consciousness

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Alkanoic Acids

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 General formula
Alkanoic Acids : CnH2n + 1COOH

That COOH makes it

easy to identify

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Reactions of Ethanoic Acids

1. Anhydrous Reactions

2. Aqueous Reactions

Before we move on
we should really
discuss Acids

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Acids - Quick Review

H+ Cl- CH3COOH
Before we move on
we should really
H+ Cl- CH3COO- H+ discuss Acids

H+ Cl- CH3COOH

Complete Partial
Dissociation Dissociation

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Reactions of Ethanoic Acids

Anhydrous Reactions

1. Ethanoic Acid burning in air or oxygen to produce CO2, Water and Heat

2. Ethanoic Acid + Alcohols to produce Esters and Water ← We will discuss this later

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Aqueous Reactions Reactions of Ethanoic Acids

1. Ethanoic Acid + reactive metals → Salt + Hydrogen

2CH3COOH(aq) + Mg(s) → (CH3COO)2Mg(aq) +

H2(g)
Magnesium ethanoate

2. Ethanoic Acids + Oxides/ Hydroxides → Salt + water

CH3COOH(aq) + CuO(s) → Cu(CH3COO)2(aq) + H2O(l)

Copper(II) ethanoate

3. Ethanoic Acids + Carbonate / Hydrogen Carbonates → Salt + Water + CO2

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Homologous Series - by now we know organic compounds are grouped into distinct
groups known as homologous series.

Patterns we notice -
1. All members contain the same functional group

2. All members have the same general formula

3. Members of a group have similar chemical properties and reactivity decreases as the amount

of carbon atoms increase.

4. Physical properties show graduation along the series. As the amount of carbon atoms increase so does

density, boiling and melting points.

5. Each subsequent member differs by CH2

6. Members of a group can be prepared using similar methods

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Esters

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 General formula
Esters: CnH2n +1 COOCx H2x+1
Conc. H2SO4 + heat

Ethanoic Acid + Alcohol → Ester + Water

Naming esters

Alcohol Prefix + yl Ethanoic Acid Prefix + anoate

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Naming esters Alcohol Prefix + yl Ethanoic Acid Prefix + anoate

Let’s mix Ethanoic Acid and Ethanol

Conc. H2SO4 + heat

+ + H2O

ethly ethanoate

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Naming esters Alcohol Prefix + yl Ethanoic Acid Prefix + anoate

Let’s mix Methanoic Acid and Ethanol

Conc. H2SO4 + heat

+ + H2O

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Let’s mix Propanoic Acid and Butanol

+ H2O

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Hydrolysis of esters

Hydrolysis of esters can be thought of as reversing the process

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Hydrolysis of esters

There are two types of Hydrolysis

1. Acid Hydrolysis - Ester is boiled with water and a dilute acid such as
H2SO4 or HCL

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Hydrolysis of esters

Can you guess what two products will be created in the acid hydrolysis below?

Propanoic Acid + Methanol

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Hydrolysis of esters

2. Alkaline Hydrolysis - Ester is boiled with water and an aqueous alkali such
as KOH or NaOH.

Please note is this process you do not end up with the Alkanoic Acid and the
Alcohol.

Instead you end up with a Salt and an Alcohol

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Hydrolysis of esters
Alkaline Hydrolysis using NaOH

Ester + Water →(OH-) Alkanoic Acid + Alcohol

Alkanoic Acid + NaOH →(OH-) Salt + Water

excess

Ester + NaOH → Salt + Alcohol

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Hydrolysis of esters
Alkaline Hydrolysis using NaOH

Alkaline Hydrolysis Summary Equation

CH3COOC2H5 (l) + NaOH(aq) → CH3COONa(aq) + C2H5OH(aq)

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Saponification of Esters
Saponification is the process by which fats and oils are hydrolysed to form soap by
boiling it with concentrated sodium hydroxide solution. e.g.

(C17H35COO)3C3H5 (l) + 3NaOH(aq) → 3(C17H35COO)Na (aq) + C3H5(OH)3(aq)

Glyceryl Tristearate
(Fats and oils are
natural esters)
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Manufacture of Soapless Detergents (synthetic)
Detergents are made by reaction concentrated sulphuric acid with hydrocarbons
from petroleum. The product is them neutralized with NaOH to form sodium salts.

E.g. of a detergent is:

C12H25OSO3Na C12H25OSO3- Na+

Hydrophobic tail
(covalent)
Hydrophilic head
(ionic)
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So how do detergents work?
1. They lower the intermolecular forces between the water molecules and this allows the
water spread out and wet surfaces more efficiently

2. They break up and disperse grease using the hydrophobic tail and hydrophilic head

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 Agitation causes the
detergent molecule to lift the
dirt / grease from the cloth

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 Soaps vs Detergents

Soap Detergent

Do no lather in hard water. It will instead

Lather in hard water
form an unpleasant scum made up of
(does not form an unpleasant scum)
insoluble calcium and magnesium stearate.

Older ones were non-biodegradable

They are biodegradable
Newer varieties are biodegradable

Do contain phosphates which pollute

Does not contain phosphates
causing eutrophication

Manufactures from renewable sources Manufactures from non-renewable sources

(fats and oils) (petroleum)

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CSEC
Polymers
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Definitions

Polymers are macromolecules formed by linking together fifty (50) or more small molecules
called monomers.

Addition polymerisation occurs when unsaturated monomers are linked to form a

saturated polymer. This type of polymer has the same empirical formula as the
monomer.

Condensation polymerisation occurs when monomers join and in the process

eliminate a small molecule such as water.

The properties of a polymer will obviously depend on the type of

polymer and the type of linkage (addition or condensation)

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Polymerisation Type Category of polymer Synthetic Natural

Addition Polyalkenes ● Polyethene N/A

Polymerisation ● Polypropene
● Polystyrene
● Polyvinyl Chloride (PVC)
● Teflon

Condensation Polyamide Nylon Proteins

Polymerisation
Polyesters Terylene N/A

Polysaccharides N/A Starch

Next we need to learn off a few uses of each… this is so annoying !

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 Garbage and Grocery
Polyethene Agricultural Mulch
Bags

Polypropene Packaging Plastic parts for

machines

Polystyrene Disposable cutlery CD cases

Polyvinyl
Window frames Drainage Pipes
Chloride (PVC)

Teflon Waterproof fabric Non-stick cookware

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 Nylon Clothing Rope and thread

Terylene Nets and sails Raincoats

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 Trick Question
What is the name of the polymer?

If X = CH3

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What’s going on here?

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Cracking

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Cracking:

1. Thermal Cracking - Uses heat only

(450oC - 750oC at 70 atmospheric pressure)

2. Catalytic Cracking - Uses heat and catalyst Cracking involves the formation
(480oC - 550oC at < 5 atmospheric pressure) of at least one alkene

Cracking is the process by which heavy (larger) hydrocarbon molecules are broken up into
lighter (smaller) molecules by means of heat and usually pressure and sometimes catalysts
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 Gaseous fuel used for
domestic use e.g. gas
cookers / natural gas
C1 - C4

C5 - C12 Fuel for internal combustion

engines e.g. light aircraft
and cars

Fuel for jet engines, kerosene

C12 - C18 lamps and paraffin-oil

Used for diesel engines e.g.

C18 - C25 trains, buses and tractors

Fuel for factory boilers, ships,

C20 - C34 petroleum jelly and polishing
waxes

Used for road surfacing and

>C30 roofing
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