Organic Chemistry AS Level Notes
Table of Contents
General ............................................................................................................................................... 2-5
Basic Stuff ............................................................................................................................................................................................................... 2
Isomerism .............................................................................................................................................................................................................. 3
Fractional Distillation ....................................................................................................................................................................................... 4
Pollution ................................................................................................................................................................................................................. 5
Haloalkanes ....................................................................................................................................... 6-13
Free Radical Substitution ................................................................................................................................................................................ 6
The Ozone Layer and CFCs ......................................................................................................................................................................... 7-8
Practical: Hydrolysis of Haloalkanes.......................................................................................................................................................... 9
Nucleophilic Substitution .......................................................................................................................................................................10-12
Cyanide Ions ................................................................................................................................................................................................... 10
Hydroxide Ions ............................................................................................................................................................................................... 11
Ammonia.......................................................................................................................................................................................................... 12
Elimination Reactions .....................................................................................................................................................................................11
Amines ...................................................................................................................................................................................................................13
Alkenes ........................................................................................................................................... 14-18
Structure and Bonding ...................................................................................................................................................................................14
Electrophilic Addition ..............................................................................................................................................................................14-17
Hydrogen Bromide ....................................................................................................................................................................................... 15
Bromine ............................................................................................................................................................................................................ 17
Sulfuric Acid.................................................................................................................................................................................................... 17
Major and Minor Products ............................................................................................................................................................................16
Addition Polymerisation ...............................................................................................................................................................................18
Alcohols .......................................................................................................................................... 19-23
Alcohols .................................................................................................................................................................................................................19
Elimination Reaction (Dehydration of Alcohols) ................................................................................................................................19
Manufacture of Alcohols .........................................................................................................................................................................20-21
Hydration of Alkenes ................................................................................................................................................................................... 20
Fermentation of Glucose ............................................................................................................................................................................ 21
Oxidation of Alcohols ...............................................................................................................................................................................22-23
Organic Analysis ................................................................................................................................... 24
Infrared Spectroscopy ....................................................................................................................................................................................24
Mass Spectrometry ..........................................................................................................................................................................................24
1
,Basic Stuff
Special Features of Carbon
• Can from strong covalent bonds to each other.
• Carbon-carbon bonds can be single/double/triple.
• Carbon atoms can be arranged in straight chains, branched chains and rings.
• Other atoms/groups can be placed on the carbon atoms and in different positions.
Homologous Series
A series of compound similar in structure, in which each member differs from the next by a common repeating unit,
CH2.
• Share a general formula
• Same functional group (similar chemical properties)
• Gradual change in physical properties
Skeletal Formula
A short hand used to show the formula of larger molecules
• Each straight line represents a single bond between two carbon atoms.
• Only functional groups are added in.
Examples:
Butane
Ethanol
Propene
Cyclohexane
2
, Isomerism
Structural Isomers:
Molecules that share the same molecular formula but have different structural formulae.
• Chain – different arrangement of same carbon skeleton
• Position – functional group in different placement
• Functional – different functional groups
Stereoisomerism:
Stereoisomers have the same structural formulae, but their atoms take up different arrangements in space
• Geometric / E/Z
• Optical
Geometric Isomerism:
Geometric isomers occur in molecules where there is restricted rotation around a double bond. This locks the groups
either side of the C=C bond in position.
Cahn-Ingold-Prelog (CIP) Rule
The E/Z system works by assigning relative priority to the 2 groups on each carbon of the double bond.
1. Rank the atoms attached directly to each carbon atom in the double bond based on largest atomic number.
2. If the first atoms are identical, then rank the 2nd, 3rd, 4th, etc. until a difference is found.
E = Opposite Z = Together
3
Table of Contents
General ............................................................................................................................................... 2-5
Basic Stuff ............................................................................................................................................................................................................... 2
Isomerism .............................................................................................................................................................................................................. 3
Fractional Distillation ....................................................................................................................................................................................... 4
Pollution ................................................................................................................................................................................................................. 5
Haloalkanes ....................................................................................................................................... 6-13
Free Radical Substitution ................................................................................................................................................................................ 6
The Ozone Layer and CFCs ......................................................................................................................................................................... 7-8
Practical: Hydrolysis of Haloalkanes.......................................................................................................................................................... 9
Nucleophilic Substitution .......................................................................................................................................................................10-12
Cyanide Ions ................................................................................................................................................................................................... 10
Hydroxide Ions ............................................................................................................................................................................................... 11
Ammonia.......................................................................................................................................................................................................... 12
Elimination Reactions .....................................................................................................................................................................................11
Amines ...................................................................................................................................................................................................................13
Alkenes ........................................................................................................................................... 14-18
Structure and Bonding ...................................................................................................................................................................................14
Electrophilic Addition ..............................................................................................................................................................................14-17
Hydrogen Bromide ....................................................................................................................................................................................... 15
Bromine ............................................................................................................................................................................................................ 17
Sulfuric Acid.................................................................................................................................................................................................... 17
Major and Minor Products ............................................................................................................................................................................16
Addition Polymerisation ...............................................................................................................................................................................18
Alcohols .......................................................................................................................................... 19-23
Alcohols .................................................................................................................................................................................................................19
Elimination Reaction (Dehydration of Alcohols) ................................................................................................................................19
Manufacture of Alcohols .........................................................................................................................................................................20-21
Hydration of Alkenes ................................................................................................................................................................................... 20
Fermentation of Glucose ............................................................................................................................................................................ 21
Oxidation of Alcohols ...............................................................................................................................................................................22-23
Organic Analysis ................................................................................................................................... 24
Infrared Spectroscopy ....................................................................................................................................................................................24
Mass Spectrometry ..........................................................................................................................................................................................24
1
,Basic Stuff
Special Features of Carbon
• Can from strong covalent bonds to each other.
• Carbon-carbon bonds can be single/double/triple.
• Carbon atoms can be arranged in straight chains, branched chains and rings.
• Other atoms/groups can be placed on the carbon atoms and in different positions.
Homologous Series
A series of compound similar in structure, in which each member differs from the next by a common repeating unit,
CH2.
• Share a general formula
• Same functional group (similar chemical properties)
• Gradual change in physical properties
Skeletal Formula
A short hand used to show the formula of larger molecules
• Each straight line represents a single bond between two carbon atoms.
• Only functional groups are added in.
Examples:
Butane
Ethanol
Propene
Cyclohexane
2
, Isomerism
Structural Isomers:
Molecules that share the same molecular formula but have different structural formulae.
• Chain – different arrangement of same carbon skeleton
• Position – functional group in different placement
• Functional – different functional groups
Stereoisomerism:
Stereoisomers have the same structural formulae, but their atoms take up different arrangements in space
• Geometric / E/Z
• Optical
Geometric Isomerism:
Geometric isomers occur in molecules where there is restricted rotation around a double bond. This locks the groups
either side of the C=C bond in position.
Cahn-Ingold-Prelog (CIP) Rule
The E/Z system works by assigning relative priority to the 2 groups on each carbon of the double bond.
1. Rank the atoms attached directly to each carbon atom in the double bond based on largest atomic number.
2. If the first atoms are identical, then rank the 2nd, 3rd, 4th, etc. until a difference is found.
E = Opposite Z = Together
3
