1. A guide for GCSE students KNOCKHARDY PUBLISHING
ORGANIC CHEMISTRY
A guide for GCSE students
2010 SPECIFICATIONS
KNOCKHARDY PUBLISHING

2. ORGANIC CHEMISTRY INTRODUCTION www.knockhardy.org.uk
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...
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.

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

4. ORGANIC CHEMISTRY DISTILLATION OF CRUDE OIL THE PETROCHEMICAL INDUSTRY
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.

5. ORGANIC CHEMISTRY
WHAT IS IT?

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

7. 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

8. 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

9. 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 STRAIGHT CHAINS
BRANCHED CHAINS
and RINGS

10. 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 STRAIGHT CHAINS
BRANCHED CHAINS
and RINGS
• OTHER ATOMS/GROUPS OF ATOMS ARE PLACED ON CARBON ATOMS

11. 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 STRAIGHT CHAINS
BRANCHED CHAINS
and RINGS
• OTHER ATOMS/GROUPS OF ATOMS ARE PLACED ON CARBON ATOMS

12. You can also get a combination of rings and chains
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

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

14. Compounds containing only carbon and hydrogen atoms
HYDROCARBONS
Compounds containing only carbon and hydrogen atoms

15. HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE…
● A GENERAL FORMULA
● SIMILAR CHEMICAL PROPERTIES

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

17. HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE…
● A GENERAL FORMULA
● SIMILAR CHEMICAL PROPERTIES
Examples:-
ALKANES CnH2n+2 CH4 C2H6

18. HOMOLOGOUS SERIES
A FAMILY OF COMPOUNDS WHICH HAVE…
● A GENERAL FORMULA
● SIMILAR CHEMICAL PROPERTIES
Examples:-
ALKANES CnH2n+2 CH4 C2H6
ALKENES CnH2n C2H4 C3H6

19. WHAT ARE THE NEXT IN EACH SERIES?
HOMOLOGOUS SERIES
WHAT ARE THE NEXT IN EACH SERIES?
ALKANES ALKENES
CH4
C2H6 C2H4
? C3H6
? ?
? ?

20. WHAT ARE THE NEXT IN EACH SERIES?
HOMOLOGOUS SERIES
WHAT ARE THE NEXT IN EACH SERIES?
ALKANES ALKENES
CH4
C2H6 C2H4
C3H8 C3H6
C4H10 C4H8
C5H12 C5H10

21. SATURATED HYDROCARBONS
ALKANES
SATURATED HYDROCARBONS

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

23. 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

24. ALKANE STRUCTURES H
H – C – H
METHANE ETHANE PROPANE
CH C2H C3H8

25. ALKANE STRUCTURES H
H – C – H
H H
H – C – C – H
METHANE ETHANE PROPANE
CH C2H C3H8

26. METHANE ETHANE PROPANE CH4 C2H6 C3H8
ALKANE STRUCTURES H
H – C – H
H H
H – C – C – H
H H H
H – C – C – C – H
METHANE ETHANE PROPANE
CH C2H C3H8
THESE ARE DISPLAYED STRUCTURES
THEY SHOW ALL THE
COVALENT BONDS IN THE MOLECULE
Each covalent bond is represented by a line

27. ALKANE STRUCTURES H
H – C – H
H H
H – C – C – H
H H H
H – C – C – C – H
METHANE ETHANE PROPANE
CH C2H C3H8
H H H H
H – C – C – C – C – H
BUTANE C4H10

28. ALKANE STRUCTURES HOWEVER
H – C – H
H H
H – C – C – H
H H H
H – C – C – C – H
METHANE ETHANE PROPANE
CH C2H C3H8
H H H H
H – C – C – C – C – H
BUTANE C4H10
HOWEVER
By the time you get to butane, there are two ways to arrange the carbon and hydrogen atoms…

29. C4H10 ALKANE STRUCTURES H H – C – H H – C ––– C ––– C – H H H H
H – C – C – C – C – H
BUTANE
METHYLPROPANE
STRUCTURAL ISOMERS
Compounds with the SAME MOLECULAR FORMULA but DIFFERENT STRUCTURAL FORMULA

30. THESE ARE ALL THE SAME STRUCTURE
ALKANE STRUCTURES
H H H H
H C C C C H
H H H H
BEWARE!
THESE ARE ALL THE SAME STRUCTURE H
H C H H
H C C H
H H C H
H H H
H C C C H
H H H C H H

31. HOW MANY ISOMERS ARE THERE?
ISOMERS OF PENTANE
C5H12
HOW MANY ISOMERS ARE THERE?

32. ISOMERS OF PENTANE
C5H12
THERE ARE 3 ISOMERS

33. ISOMERS OF PENTANE H H H H H C5H12 H C C C C C H H H H H H
THERE ARE 3 ISOMERS

34. ISOMERS OF PENTANE H H H H H C5H12 H C C C C C H H H H H H H H H H
THERE ARE 3 ISOMERS
H H H H
H C C C C H
H H H
H C H H

35. ISOMERS OF PENTANE H H H H H C5H12 H C C C C C H H H H H H H H H H H H
THERE ARE 3 ISOMERS
H H
H C C C H
H C H H
H H H H
H C C C C H
H H H
H C H H

36. SOME PROPERTIES OF ALKANES

37. SOME PROPERTIES OF ALKANES
Boiling point increases as they get more carbon atoms in the formula
CH4 (-161°C) C2H6 (-88°C) C3H8 (-42°C) C4H10 (-0.5°C)

38. SOME PROPERTIES OF ALKANES
Boiling point increases as they get more carbon atoms in the formula
CH4 (-161°C) C2H6 (-88°C) C3H8 (-42°C) C4H10 (-0.5°C)
Viscosity Greater number of C atoms = greater viscosity
Flammability Greater number of C atoms = less flammable

39. SOME PROPERTIES OF ALKANES
Boiling point increases as they get more carbon atoms in the formula
CH4 (-161°C) C2H6 (-88°C) C3H8 (-42°C) C4H10 (-0.5°C)
Viscosity Greater number of C atoms = greater viscosity
Flammability Greater number of C atoms = less flammable
Use as fuels Alkanes make useful fuels
CH O2 CO H2O

40. SOME PROPERTIES OF ALKANES
Boiling point increases as they get more carbon atoms in the formula
CH4 (-161°C) C2H6 (-88°C) C3H8 (-42°C) C4H10 (-0.5°C)
Viscosity Greater number of C atoms = greater viscosity
Flammability Greater number of C atoms = less flammable
Use as fuels Alkanes make useful fuels
The more carbon atoms they have the more oxygen they need
CH O2 CO H2O
C3H O CO H2O

41. UNSATURATED HYDROCARBONS
ALKENES
UNSATURATED HYDROCARBONS

42. 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

43. 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

44. C C C C C H H H ALKENE STRUCTURES H H H H H ETHENE PROPENE C2H4 C3H6
DOUBLE COVALENT BOND
H H
C C
H H H
C C C H
H H
ETHENE PROPENE
C2H C3H6

45. HOW CAN YOU TELL THEM APART?
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. A B C
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
A B C

46. C2H4 + Br2 C2H4Br2 H C C H H C C H H H H H ADDITION REACTIONS Br Br
BROMINE
C2H Br C2H4Br2
Br Br
H C C H
H H
Br Br
H C C H
H H
ETHENE ,2-DIBROMOETHANE
THIS REACTION IS USED AS A TEST FOR UNSATURATION - BROMINE WATER IS ‘DECOLOURISED’.

47. C2H4 + H2 C2H6 H C C H H C C H ADDITION REACTIONS H H H H HYDROGEN
CATALYST
C2H H C2H6
H H
H C C H
H H
H C C H
ETHENE ETHANE
VEGETABLE OILS CONTAINING UNSATURATED FATS ARE HARDENED TO FORM MARGARINE THIS WAY

48. POLYMERISATION
For more detailed information on POLYMERS, please see the appropriate Powerpoint on the Knockhardy GCSE site.

49. 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

50. 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

51. 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 poly(ethene)
MONOMER POLYMER

52. 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
the number of repeating units is the same as the number of original molecules
n represents a large number
ethene poly(ethene)
MONOMER POLYMER

53. The animation shows the monomers turning into the polymer
POLYMERISATION
The animation shows the monomers turning into the polymer

54. ALCOHOLS

55. ALCOHOLS WHAT ARE THEY? ● NOT HYDROCARBONS
● CONTAIN THE –OH FUNCTIONAL GROUP

56. ALCOHOLS WHAT ARE THEY? ● NOT HYDROCARBONS
● CONTAIN THE –OH FUNCTIONAL GROUP
● EXAMPLES… METHANOL CH3OH
ETHANOL C2H5OH
PROPANOL C3H7OH
GENERAL FORMULA IS… CnH2n+1OH

57. H C O H H C C O H H C C C O H ALCOHOL STRUCTURES H H H
METHANOL ETHANOL
CH3OH C2H5OH
H H H
H C C C O H
PROPANOL
C3H7OH

58. H C C C O H STRUCTURAL ISOMERS OF PROPANOL H H H PROPANOL
There is another alcohol with the same molecular formula
What is it?
PROPANOL
C3H7OH or CH3CH2CH2OH

59. H C C C O H H C C C H H O H H STRUCTURAL ISOMERS OF PROPANOL H H H
There is another alcohol with the same molecular formula
What is it?
PROPAN-1-OL
C3H7OH or CH3CH2CH2OH
H H H
H C C C H
H O H H
PROPAN-2-OL
C3H7OH or CH3CH(OH)CH3

60. REACTIONS OF ALCOHOLS COMBUSTION
ALCOHOLS MAKE USEFUL FUELS
ETHANOL IS A CLEAN FUEL - DOESN’T FORM POLLUTANTS
ETHANOL CAN BE MADE BY FERMENTATION (RENEWABLE)
C2H5OH O CO H2O
ETHANOL OXYGEN CARBON WATER
DIOXIDE

61. 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 ETHANOIC ACID
Wine Vinegar

62. REACTIONS OF ALCOHOLS ESTERIFICATION
ALCOHOLS REACT WITH CARBOXYLIC ACIDS
THE REACTION IS REVERSIBLE
COMPOUNDS CALLED ESTERS ARE FORMED
ESTERS HAVE CHARACTERISTIC SMELLS
CH3COOH C2H5OH CH3COOC2H H2O
ETHANOIC ETHANOL ETHYL WATER
ACID ETHANOATE

63. REACTIONS OF ALCOHOLS REACTION WITH SODIUM
ALCOHOLS REACT WITH SODIUM
HYDROGEN GAS IS PRODUCED
2Na C2H5OH C2H5ONa H2
SODIUM ETHANOL SODIUM HYDROGEN
ETHOXIDE

64. INDUSTRIAL PREPARATION OF ALCOHOLS

65. INDUSTRIAL PREPARATION OF ALCOHOLS
1. FERMENTATION
Reagent(s) GLUCOSE - produced by the hydrolysis of starch
Conditions yeast
warm, but no higher than 37°C
Equation C6H12O6 ——> 2 C2H5OH CO2
SUGAR ETHANOL CARBON
(GLUCOSE) DIOXIDE

66. INDUSTRIAL PREPARATION OF ALCOHOLS
1. FERMENTATION
Reagent(s) GLUCOSE - produced by the hydrolysis of starch
Conditions yeast
warm, but no higher than 37°C
Equation C6H12O6 ——> 2 C2H5OH CO2
Advantages LOW ENERGY PROCESS
USES RENEWABLE RESOURCES - PLANT MATERIAL
SIMPLE EQUIPMENT
Disadvantages SLOW
PRODUCES IMPURE ETHANOL
BATCH PROCESS

67. 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 C2H H2O ——> 2 C2H5OH
ETHENE STEAM ETHANOL

68. 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 C2H H2O ——> 2 C2H5OH
Advantages FAST
PURE ETHANOL PRODUCED
CONTINUOUS PROCESS
Disadvantages HIGH ENERGY PROCESS
EXPENSIVE PLANT REQUIRED
USES NON-RENEWABLE FOSSIL FUELS TO MAKE ETHENE

69. INDUSTRIAL PREPARATION OF ALCOHOLS
USES OF ETHANOL
ALCOHOLIC DRINKS
SOLVENT industrial alcohol / methylated spirits
FUEL petrol substitute in countries with limited oil reserves

70. CARBOXYLIC ACIDS

71. CARBOXYLIC ACIDS WHAT ARE THEY? ● NOT HYDROCARBONS
● CONTAIN THE –COOH FUNCTIONAL GROUP

72. CARBOXYLIC ACIDS WHAT ARE THEY? ● NOT HYDROCARBONS
● CONTAIN THE –COOH FUNCTIONAL GROUP
● EXAMPLES… METHANOIC ACID HCOOH
ETHANOIC ACID CH3COOH
PROPANOIC ACID C2H5COOH

73. CARBOXYLIC ACID STRUCTURES
H C O H
H O
H C C O H H
METHANOIC ACID ETHANOIC ACID
HCOOH CH3COOH

74. 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

75. 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

76. ESTERS

77. ESTERS WHAT ARE THEY? ● NOT HYDROCARBONS
● CONTAIN THE –COOC FUNCTIONAL GROUP

78. 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) METHYL (HCOOCH3)
ACID METHANOATE
ETHANOIC (CH3COOH) METHYL (CH3COOCH3)
ACID ETHANOATE

79. 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) METHYL (HCOOCH3)
ACID METHANOATE
ETHANOIC (CH3COOH) METHYL (CH3COOCH3)
ACID ETHANOATE
● USE… Flavourings – many have fruity odours

80. QUESTIONS

81. WHICH FORMULAE REPRESENT ALKANES?
QUESTIONS
WHICH FORMULAE REPRESENT ALKANES?
C10H22 C3H6 C2H6
C2H6O C6H12O6 C3H7COOH

82. WHICH FORMULAE REPRESENT ALKANES?
QUESTIONS
WHICH FORMULAE REPRESENT ALKANES?
C10H22 C3H6 C2H6
C2H6O C6H12O6 C3H7COOH

83. CARBOXYLIC ACID OR ESTER?
QUESTIONS
CARBOXYLIC ACID OR ESTER?
HCOOC2H5
C3H7COOH
C6H6COOCH3
C2H5COOC3H7
CH3COOH

84. CARBOXYLIC ACID OR ESTER?
QUESTIONS
CARBOXYLIC ACID OR ESTER?
HCOOC2H5 ESTER
C3H7COOH CARBOXYLIC ACID
C6H6COOCH3 ESTER
C2H5COOC3H7 ESTER
CH3COOH CARBOXYLIC ACID

85. WHAT TYPES OF ORGANIC COMPOUND ARE THESE?
QUESTIONS
WHAT TYPES OF ORGANIC COMPOUND ARE THESE?
H H H
H – C – C – C – H
H H O
H C C C O H
H H
H H
H C C H
H O H
H H O H
H C C C O C H
H H H

86. WHAT TYPES OF ORGANIC COMPOUND ARE THESE?
QUESTIONS
WHAT TYPES OF ORGANIC COMPOUND ARE THESE?
H H H
H – C – C – C – H
H H O
H C C C O H
H H
CARBOXYLIC ACID
ALKANE
H H
H C C H
H O H
H H O H
H C C C O C H
H H H
ALCOHOL
ESTER

87. ©2011 JONATHAN HOPTON & KNOCKHARDY PUBLISHING
ORGANIC CHEMISTRY
THE END
©2011 JONATHAN HOPTON & KNOCKHARDY PUBLISHING