ORGANIC

CHEMISTRY
A guide for GCSE students

KNOCKHARDY PUBLISHING

2010

SPECIFICATIONS

ORGANIC CHEMISTRY
INTRODUCTION
This Powerpoint show is one of several produced to help students
understand selected GCSE Chemistry topics. It is based on the requirements
of the AQA specification but is suitable for other examination boards.
Individual students may use the material at home for revision purposes and
it can also prove useful for classroom teaching with an interactive white
board.
Accompanying notes on this, and the full range of AS and A2 Chemistry
topics, are available from the KNOCKHARDY WEBSITE at...

www.knockhardy.org.uk

All diagrams, photographs and any animations in this Powerpoint are

original and created by Jonathan Hopton. Permission must be
obtained for their use in any work that is distributed for financial gain.

ORGANIC CHEMISTRY
CONTENTS
What is organic chemistry?
Hydrocarbons
Alkanes
Alkenes
Alcohols
Industrial preparation of alcohols
Carboxylic acids and esters
Questions

ORGANIC CHEMISTRY
This Powerpoint presentation does not cover

DISTILLATION OF CRUDE OIL

THE PETROCHEMICAL INDUSTRY
POLYMERS
For further information on these topics, please see the other
Powerpoints on the Knockhardy GCSE site.

ORGANIC CHEMISTRY
WHAT IS IT?

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...
CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...
CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER
THE CARBON-CARBON BONDS CAN BE SINGLE, DOUBLE OR TRIPLE

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...
CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER
THE CARBON-CARBON BONDS CAN BE SINGLE, DOUBLE OR TRIPLE
CARBON ATOMS CAN BE ARRANGED IN
and

STRAIGHT CHAINS
BRANCHED CHAINS
RINGS

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...
CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER
THE CARBON-CARBON BONDS CAN BE SINGLE, DOUBLE OR TRIPLE
CARBON ATOMS CAN BE ARRANGED IN
and

STRAIGHT CHAINS
BRANCHED CHAINS
RINGS

OTHER ATOMS/GROUPS OF ATOMS ARE PLACED ON CARBON ATOMS

ORGANIC CHEMISTRY
WHAT IS IT?
Organic chemistry is the study of carbon compounds. It is such a complex
branch of chemistry because...
CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER
THE CARBON-CARBON BONDS CAN BE SINGLE, DOUBLE OR TRIPLE
CARBON ATOMS CAN BE ARRANGED IN
and

STRAIGHT CHAINS
BRANCHED CHAINS
RINGS

OTHER ATOMS/GROUPS OF ATOMS ARE PLACED ON CARBON ATOMS

ORGANIC CHEMISTRY
CHAINS AND RINGS
CARBON ATOMS CAN BE ARRANGED IN

STRAIGHT CHAINS

BRANCHED CHAINS

and

RINGS

You can also get a combination of rings and chains

ORGANIC CHEMISTRY
SINGLE AND MULTIPLE BONDING
CARBON-CARBON COVALENT BONDS CAN BE SINGLE, DOUBLE OR TRIPLE

HYDROCARBONS
Compounds containing only
carbon and hydrogen atoms

HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE
A GENERAL FORMULA
SIMILAR CHEMICAL PROPERTIES

HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE
A GENERAL FORMULA
SIMILAR CHEMICAL PROPERTIES
Examples:-

HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE
A GENERAL FORMULA
SIMILAR CHEMICAL PROPERTIES
Examples:ALKANES

CnH2n+2

CH4

C2H6

HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE
A GENERAL FORMULA
SIMILAR CHEMICAL PROPERTIES
Examples:ALKANES

CnH2n+2

CH4

C2H6

ALKENES

CnH2n

C2H4

C3H6

HOMOLOGOUS SERIES
WHAT ARE THE NEXT IN EACH SERIES?
ALKANES

ALKENES

CH4
C2 H6

C2 H4

C3 H6

HOMOLOGOUS SERIES
WHAT ARE THE NEXT IN EACH SERIES?
ALKANES

ALKENES

CH4
C2 H6

C2 H4

C3 H8

C3 H6

C4H10

C4 H8

C5H12

C5H10

ALKANES
SATURATED
HYDROCARBONS

ALKANES
WHAT ARE THEY?
HYDROCARBONS
CARBON ATOMS ARE JOINED BY SINGLE COVALENT BONDS
CONTAIN THE MAXIMUM NUMBER OF HYDROGEN ATOMS
ARE SATURATED HYDROCARBONS

ALKANES
WHAT ARE THEY?
HYDROCARBONS
CARBON ATOMS ARE JOINED BY SINGLE COVALENT BONDS
CONTAIN THE MAXIMUM NUMBER OF HYDROGEN ATOMS
ARE SATURATED HYDROCARBONS
EXAMPLES

METHANE

CH4

ETHANE

C2H6

PROPANE

C3H8

BUTANE

C4H10

GENERAL FORMULA IS

CnH2n+2

ALKANE STRUCTURES
H
HCH
H
METHANE
CH4

ETHANE
C2H6

PROPANE
C3H8

ALKANE STRUCTURES
H
HCH
H
METHANE
CH4

HCCH
H

ETHANE
C2H6

PROPANE
C3H8

ALKANE STRUCTURES
H

HCH
H

HCCH
H

METHANE
CH4

ETHANE
C2H6

HCCCH
H

PROPANE
C3H8

THESE
THESEARE
AREDISPLAYED
DISPLAYEDSTRUCTURES
STRUCTURES
THEY
THEYSHOW
SHOWALL
ALLTHE
THE
COVALENT
COVALENTBONDS
BONDSIN
INTHE
THEMOLECULE
MOLECULE
Each
Eachcovalent
covalentbond
bondis
isrepresented
representedby
byaaline
line

ALKANE STRUCTURES
H

HCH

HCCH

METHANE
CH4

BUTANE

ETHANE
C2H6

HCCCCH
H

H
C4H10

HCCCH
H

PROPANE
C3H8

ALKANE STRUCTURES
H

HCH

METHANE
CH4

BUTANE

H
C4H10

HCCCH
H

ETHANE
C2H6

HCCCCH
H

HCCH

PROPANE
C3H8

HOWEVER
HOWEVER
By
Bythe
thetime
timeyou
youget
getto
tobutane,
butane,
there
thereare
aretwo
twoways
waysto
toarrange
arrangethe
the
carbon
carbonand
andhydrogen
hydrogenatoms
atoms

ALKANE STRUCTURES

C4H10

H
HCH

HCCCCH
H

BUTANE

H C C C H
H

METHYLPROPANE
STRUCTURAL ISOMERS

Compounds with the SAME MOLECULAR FORMULA

but DIFFERENT STRUCTURAL FORMULA

ALKANE STRUCTURES

BEWARE!
BEWARE!
THESE
THESEARE
AREALL
ALL
THE
THESAME
SAME
STRUCTURE
STRUCTURE

H
H C H H
H

HH C H
H

H H C H
H

ISOMERS OF PENTANE

C
C55H
H1212
HOW
HOW MANY
MANY ISOMERS
ISOMERS
ARE
ARE THERE?
THERE?

ISOMERS OF PENTANE
CC55HH1212
THERE
THEREARE
ARE
33ISOMERS
ISOMERS

ISOMERS OF PENTANE

CC55HH1212
H

THERE
THEREARE
ARE
33ISOMERS
ISOMERS

ISOMERS OF PENTANE

H
H
H C H
H

CC55HH1212
H

THERE
THEREARE
ARE
33ISOMERS
ISOMERS

ISOMERS OF PENTANE

CC55HH1212
THERE
THEREARE
ARE
33ISOMERS
ISOMERS

H
H C H
H
H

H
H
H C H

H
H
H C H

SOME PROPERTIES OF ALKANES

SOME PROPERTIES OF ALKANES

Boiling point

increases as they get more carbon atoms in the formula

CH4 (-161C)

C2H6 (-88C)

C3H8 (-42C)

C4H10 (-0.5C)

SOME PROPERTIES OF ALKANES

Boiling point

increases as they get more carbon atoms in the formula

CH4 (-161C)

C2H6 (-88C)

C3H8 (-42C)

C4H10 (-0.5C)

Viscosity

Greater number of C atoms = greater viscosity

Flammability

Greater number of C atoms = less flammable

SOME PROPERTIES OF ALKANES

Boiling point

increases as they get more carbon atoms in the formula

CH4 (-161C)

C2H6 (-88C)

C3H8 (-42C)

C4H10 (-0.5C)

Viscosity

Greater number of C atoms = greater viscosity

Flammability

Greater number of C atoms = less flammable

Use as fuels

Alkanes make useful fuels

CH4

2O2

CO2 + 2H2O

SOME PROPERTIES OF ALKANES

Boiling point

increases as they get more carbon atoms in the formula

CH4 (-161C)

C2H6 (-88C)

C3H8 (-42C)

C4H10 (-0.5C)

Viscosity

Greater number of C atoms = greater viscosity

Flammability

Greater number of C atoms = less flammable

Use as fuels

Alkanes make useful fuels

CH4

2O2

CO2 + 2H2O

The more carbon atoms they have the more oxygen they need

C3H8

5O2

3CO2 + 4H2O

ALKENES
UNSATURATED
HYDROCARBONS

ALKENES
WHAT ARE THEY?
HYDROCARBONS
CONTAIN A DOUBLE C=C COVALENT BOND
ARE UNSATURATED HYDROCARBONS THEY CAN HAVE
ATOMS ADDED TO THEM
ARE MORE REACTIVE THAN ALKANES

ALKENES
WHAT ARE THEY?
HYDROCARBONS
CONTAIN A DOUBLE C=C COVALENT BOND
ARE UNSATURATED HYDROCARBONS THEY CAN HAVE
ATOMS ADDED TO THEM
ARE MORE REACTIVE THAN ALKANES
EXAMPLES

ETHENE

C2H4

PROPENE

C3H6

BUTENE

C4H8

GENERAL FORMULA IS

CnH2n

ALKENE STRUCTURES
DOUBLE COVALENT BOND

ETHENE
C2H4

H
PROPENE
C3H6

ALKANES & ALKENES

HOW CAN YOU TELL THEM APART?
ADD BROMINE WATER; if the reddish-brown colour is removed the substance
possesses a C=C bond.

PLACE A SOLUTION OF BROMINE

IN A TEST TUBE

ADD THE HYDROCARBON TO BE

TESTED AND SHAKE

IF THE BROWN COLOUR

DISAPPEARS THEN THE
HYDROCARBON IS AN ALKENE

ADDITION REACTIONS
BROMINE

C2H4

Br

Br

ETHENE

Br2

C2H4Br2

Br

Br

1,2-DIBROMOETHANE

THIS REACTION IS USED AS A TEST FOR UNSATURATION BROMINE WATER IS DECOLOURISED.

ADDITION REACTIONS
HYDROGEN

C2H4

ETHENE

H2

CATALYST

C2H6

ETHANE

VEGETABLE OILS CONTAINING UNSATURATED FATS

ARE HARDENED TO FORM MARGARINE THIS WAY

POLYMERISATION

For more detailed information on

POLYMERS, please see the appropriate
Powerpoint on the Knockhardy GCSE site.
www.knockhardy.org.uk/gcse.htm

POLYMERISATION
during polymerisation, alkenes undergo an addition reaction
all the atoms in the original alkenes are used to form the polymer
long hydrocarbon chains are formed

POLYMERISATION
during polymerisation, alkenes undergo an addition reaction
all the atoms in the original alkenes are used to form the polymer
long hydrocarbon chains are formed

POLYMERISATION
during polymerisation, alkenes undergo an addition reaction
all the atoms in the original alkenes are used to form the polymer
long hydrocarbon chains are formed

the equation shows the original monomer and

the repeating unit in the polymer

ethene
MONOMER

poly(ethene)
POLYMER

POLYMERISATION
during polymerisation, alkenes undergo an addition reaction
all the atoms in the original alkenes are used to form the polymer
long hydrocarbon chains are formed

the equation shows the original monomer and

the repeating unit in the polymer

n represents a
large number

ethene
MONOMER

poly(ethene)
POLYMER

the number of
repeating units is
the same as the
number of original
molecules

POLYMERISATION
The animation shows the monomers turning into the polymer

ALCOHOLS

ALCOHOLS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE OH FUNCTIONAL GROUP

ALCOHOLS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE OH FUNCTIONAL GROUP

EXAMPLES

METHANOL

CH3OH

ETHANOL

C2H5OH

PROPANOL

C3H7OH

GENERAL FORMULA IS

CnH2n+1OH

ALCOHOL STRUCTURES

H
H

H
METHANOL
CH3OH

ETHANOL
C2H5OH

PROPANOL
C3H7OH

STRUCTURAL ISOMERS OF PROPANOL

There
Thereisisanother
anotheralcohol
alcoholwith
with
the
thesame
samemolecular
molecularformula
formula

PROPANOL
C3H7OH or CH3CH2CH2OH

What
Whatis
isit?
it?

STRUCTURAL ISOMERS OF PROPANOL

There
Thereisisanother
anotheralcohol
alcoholwith
with
the
thesame
samemolecular
molecularformula
formula

What
Whatis
isit?
it?

PROPAN-1-OL
C3H7OH or CH3CH2CH2OH

H
PROPAN-2-OL
C3H7OH or CH3CH(OH)CH3

REACTIONS OF ALCOHOLS
COMBUSTION
ALCOHOLS MAKE USEFUL FUELS
ETHANOL IS A CLEAN FUEL - DOESNT FORM POLLUTANTS
ETHANOL CAN BE MADE BY FERMENTATION (RENEWABLE)

C2H5OH
ETHANOL

3O2
OXYGEN

2CO2 +
CARBON
DIOXIDE

3H2O
WATER

REACTIONS OF ALCOHOLS
OXIDATION
ALCOHOLS CAN BE OXIDISED TO CARBOXYLIC ACIDS
ETHANOL IS OXIDISED TO ETHANOIC ACID (ACETIC ACID)
THIS IS WHY WINE GOES SOUR WHEN LEFT TOO LONG
Air
ETHANOL
Wine

ETHANOIC ACID
Vinegar

REACTIONS OF ALCOHOLS
ESTERIFICATION
ALCOHOLS REACT WITH CARBOXYLIC ACIDS
THE REACTION IS REVERSIBLE
COMPOUNDS CALLED ESTERS ARE FORMED
ESTERS HAVE CHARACTERISTIC SMELLS

CH3COOH + C2H5OH
ETHANOIC
ACID

ETHANOL

CH3COOC2H5 + H2O
ETHYL
ETHANOATE

WATER

REACTIONS OF ALCOHOLS
REACTION WITH SODIUM
ALCOHOLS REACT WITH SODIUM
HYDROGEN GAS IS PRODUCED

2Na
SODIUM

2C2H5OH

2C2H5ONa

ETHANOL

SODIUM
ETHOXIDE

H2

HYDROGEN

INDUSTRIAL PREPARATION OF ALCOHOLS

INDUSTRIAL PREPARATION OF ALCOHOLS

1. FERMENTATION
Reagent(s)

GLUCOSE - produced by the hydrolysis of starch

Conditions

yeast
warm, but no higher than 37C

Equation

C6H12O6
SUGAR
(GLUCOSE)

>

2 C2H5OH
ETHANOL

2 CO2
CARBON
DIOXIDE

INDUSTRIAL PREPARATION OF ALCOHOLS

1. FERMENTATION
Reagent(s)

GLUCOSE - produced by the hydrolysis of starch

Conditions

yeast
warm, but no higher than 37C

Equation

C6H12O6

Advantages

LOW ENERGY PROCESS

USES RENEWABLE RESOURCES - PLANT MATERIAL
SIMPLE EQUIPMENT

>

2 C2H5OH

Disadvantages SLOW
PRODUCES IMPURE ETHANOL
BATCH PROCESS

2 CO2

INDUSTRIAL PREPARATION OF ALCOHOLS

2. HYDRATION OF ETHENE
Reagent(s)

ETHENE - from cracking of fractions from crude oil

Conditions

catalyst - phosphoric acid

high temperature and pressure

Equation

C2H4 +
ETHENE

H2O
STEAM

>

2 C2H5OH
ETHANOL

INDUSTRIAL PREPARATION OF ALCOHOLS

2. HYDRATION OF ETHENE
Reagent(s)

ETHENE - from cracking of fractions from crude oil

Conditions

catalyst - phosphoric acid

high temperature and pressure

Equation

C2H4 +

Advantages

FAST
PURE ETHANOL PRODUCED
CONTINUOUS PROCESS

H2O

>

2 C2H5OH

Disadvantages HIGH ENERGY PROCESS

EXPENSIVE PLANT REQUIRED
USES NON-RENEWABLE FOSSIL FUELS TO MAKE ETHENE

INDUSTRIAL PREPARATION OF ALCOHOLS

USES OF ETHANOL
ALCOHOLIC DRINKS
SOLVENT
FUEL

- industrial alcohol / methylated spirits

- petrol substitute in countries with limited oil reserves

CARBOXYLIC
ACIDS

CARBOXYLIC ACIDS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE COOH FUNCTIONAL GROUP

CARBOXYLIC ACIDS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE COOH FUNCTIONAL GROUP

EXAMPLES

METHANOIC ACID

HCOOH

ETHANOIC ACID

CH3COOH

PROPANOIC ACID

C2H5COOH

CARBOXYLIC ACID STRUCTURES

O
H

H
METHANOIC ACID
HCOOH

ETHANOIC ACID
CH3COOH

CARBOXYLIC ACIDS
USES
VINEGAR CONTAINS ETHANOIC ACID
- ethanoic acid is used in the manufacture of rayon
ORANGES AND LEMONS CONTAIN CITRIC ACID
ASPIRIN IS A CARBOXYLIC ACID
- it is used for pain relief and prevention heart attacks
VITAMIN C CONTAINS ASCORBIC ACID
- it is used for pain relief and prevention heart attacks

CARBOXYLIC ACIDS
REACTIONS
WEAK ACIDS
- neutralised by alkalis to form salts
- react with carbonates making salts, carbon dioxide and water
REACT WITH ALCOHOLS TO PRODUCE ESTERS

ESTERS

ESTERS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE COOC FUNCTIONAL GROUP

ESTERS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE COOC FUNCTIONAL GROUP
FORMATION
Formed by replacing the H on the COOH of a carboxylic
acid by a carbon atom group
METHANOIC (HCOOH)
ACID

METHYL
METHANOATE

(HCOOCH3)

ETHANOIC (CH3COOH)
ACID

METHYL
ETHANOATE

(CH3COOCH3)

ESTERS
WHAT ARE THEY?
NOT HYDROCARBONS
CONTAIN THE COOC FUNCTIONAL GROUP
FORMATION
Formed by replacing the H on the COOH of a carboxylic
acid by a carbon atom group
METHANOIC (HCOOH)
ACID

METHYL
METHANOATE

(HCOOCH3)

ETHANOIC (CH3COOH)
ACID

METHYL
ETHANOATE

(CH3COOCH3)

USE

Flavourings many have fruity odours

QUESTIONS

QUESTIONS
WHICH FORMULAE REPRESENT ALKANES?

C10H22

C3H6

C2H6

C2H6O

C6H12O6 C3H7COOH

QUESTIONS
WHICH FORMULAE REPRESENT ALKANES?

C10H22

C3H6

C2H6

C2H6O

C6H12O6 C3H7COOH

QUESTIONS
CARBOXYLIC ACID OR ESTER?

HCOOC2H5
C3H7COOH
C6H6COOCH3
C2H5COOC3H7
CH3COOH

QUESTIONS
CARBOXYLIC ACID OR ESTER?

HCOOC2H5

ESTER

C3H7COOH

CARBOXYLIC ACID

C6H6COOCH3

ESTER

C2H5COOC3H7

ESTER

CH3COOH

CARBOXYLIC ACID

QUESTIONS
WHAT TYPES OF ORGANIC COMPOUND ARE THESE?

HCCCH
H

H
O

C
H

QUESTIONS
WHAT TYPES OF ORGANIC COMPOUND ARE THESE?

HCCCH
H

ALKANE

ALCOHOL

CARBOXYLIC
ACID

H
O

C
H

ESTER

ORGANIC
CHEMISTRY
THE END

2011 JONATHAN HOPTON & KNOCKHARDY PUBLISHING