A* ORGANIC CHEMISTRY
A LEVEL NOTES
Marlowe Taylor
,Contents
Introduction to organic chemistry (3.1) ................................................................................. 3
Nomenclature (3.1.1)................................................................................................................................................... 3
Reaction mechanism (3.1.2) ........................................................................................................................................ 4
Isomerism (3.1.3) ........................................................................................................................................................ 4
Alkanes (3.2) ...................................................................................................................... 5
Fractional distillation of crude oil (3.2.1) ...................................................................................................................... 5
Modification of alkanes by cracking (3.2.2) ................................................................................................................... 6
Combustion of alkanes (3.2.3) ..................................................................................................................................... 6
Chlorination of alkanes (3.2.4) ..................................................................................................................................... 7
Halogenoalkanes (3.3) ........................................................................................................ 8
Nucleophilic substitution (3.3.1) .................................................................................................................................. 8
Elimination (3.3.2) ....................................................................................................................................................... 9
Ozone depletion (3.3.3) ............................................................................................................................................... 9
Alkenes (3.4) .................................................................................................................... 10
Structure, bonding, and reactivity (3.4.1) .................................................................................................................... 10
Addition reactions of alkenes (3.4.2) .......................................................................................................................... 10
Addition polymers (3.4.3) ........................................................................................................................................... 11
Alcohols (3.5) ................................................................................................................... 12
Alcohol production (3.5.1) ......................................................................................................................................... 12
Oxidation of alcohols (3.5.2) ...................................................................................................................................... 14
Elimination (3.5.3) ..................................................................................................................................................... 15
Organic analysis (3.6) ........................................................................................................ 16
Identification of functional groups by test-tube reactions (3.6.1) ................................................................................. 16
Mass spectrometry (3.6.2) ......................................................................................................................................... 16
Infrared spectroscopy (3.6.3) ..................................................................................................................................... 17
Optical isomerism (3.7) ..................................................................................................... 18
Aldehydes and ketones (3.8) .............................................................................................. 19
Carboxylic acids and their derivatives (3.9) ......................................................................... 20
Carboxylic acids and esters (3.9.1) ............................................................................................................................ 20
Acylation (3.9.2) ........................................................................................................................................................ 21
Page 1 of 44
,Aromatic Chemistry (3.10) ................................................................................................. 23
Bonding (3.10.1) ........................................................................................................................................................ 23
Electrophilic substitution (3.10.2) .............................................................................................................................. 24
Amines (3.11) ................................................................................................................... 26
Preparation (3.11.1) ................................................................................................................................................... 26
Base properties (3.11.2) ............................................................................................................................................. 27
Nucleophilic properties (3.11.3) ................................................................................................................................. 27
Polymers (3.12)................................................................................................................. 29
Condensation polymers (3.12.1) ................................................................................................................................ 29
Biodegradability and disposal of polymers (3.12.2) ..................................................................................................... 31
Amino acids, proteins, and DNA (3.13)................................................................................ 32
Amino acids (3.13.1) .................................................................................................................................................. 32
Proteins (3.13.2) ........................................................................................................................................................ 33
Enzymes (3.13.3) ....................................................................................................................................................... 35
DNA (3.13.4) .............................................................................................................................................................. 36
Action of anticancer drugs (3.13.5)............................................................................................................................. 37
Organic synthesis (3.14) .................................................................................................... 38
NMR Spectroscopy (3.15) .................................................................................................. 40
Chromatography (3.16)...................................................................................................... 43
Page 2 of 44
, Introduction to organic chemistry (3.1)
Nomenclature (3.1.1)
- Organic compounds can be represented by:
o Empirical formula – the simplest possible whole number ratio of the different types of
atoms within the compound
o Molecular formula – formula that gives the actual number of atoms of each element in one
molecule
o General formula – shows the number of atoms of each element in a substance which has n
carbon atoms. All the molecules in a homologous series have the same general formula
o Structural formula – shows how the atoms are joined together in a molecule
o Displayed formula – shows all the bonds and atoms in a molecule
o Skeletal formula – uses lines to represent bonds. Each point represents a C atom
- Homologous series = a family of compounds with same general formula and similar chemical
properties
o Characteristics:
• Same general formula
• Same functional group
• Similar chemical properties
- Functional group: nomenclature guidelines:
Functional group Prefix Suffix
Alkane -ane
Alkene -ene
Halogenoalkane Fluoro- / Bromo- /
Chloro- / Iodo-
Alcohol Hydroxy- -ol
Aldehyde -al
Ketone Oxo- -one
Carboxylic acid -oic acid
Nitrile -nitrile
Amine Amino- -amine
Acyl chloride -oyl chloride
Acid anhydride -oic anhydride
Ester -oate
Amide -amide
- Naming priorities:
carboxylic acids > aldehydes > ketones > alcohols > alkenes > halogenoalkanes
Page 3 of 44
A LEVEL NOTES
Marlowe Taylor
,Contents
Introduction to organic chemistry (3.1) ................................................................................. 3
Nomenclature (3.1.1)................................................................................................................................................... 3
Reaction mechanism (3.1.2) ........................................................................................................................................ 4
Isomerism (3.1.3) ........................................................................................................................................................ 4
Alkanes (3.2) ...................................................................................................................... 5
Fractional distillation of crude oil (3.2.1) ...................................................................................................................... 5
Modification of alkanes by cracking (3.2.2) ................................................................................................................... 6
Combustion of alkanes (3.2.3) ..................................................................................................................................... 6
Chlorination of alkanes (3.2.4) ..................................................................................................................................... 7
Halogenoalkanes (3.3) ........................................................................................................ 8
Nucleophilic substitution (3.3.1) .................................................................................................................................. 8
Elimination (3.3.2) ....................................................................................................................................................... 9
Ozone depletion (3.3.3) ............................................................................................................................................... 9
Alkenes (3.4) .................................................................................................................... 10
Structure, bonding, and reactivity (3.4.1) .................................................................................................................... 10
Addition reactions of alkenes (3.4.2) .......................................................................................................................... 10
Addition polymers (3.4.3) ........................................................................................................................................... 11
Alcohols (3.5) ................................................................................................................... 12
Alcohol production (3.5.1) ......................................................................................................................................... 12
Oxidation of alcohols (3.5.2) ...................................................................................................................................... 14
Elimination (3.5.3) ..................................................................................................................................................... 15
Organic analysis (3.6) ........................................................................................................ 16
Identification of functional groups by test-tube reactions (3.6.1) ................................................................................. 16
Mass spectrometry (3.6.2) ......................................................................................................................................... 16
Infrared spectroscopy (3.6.3) ..................................................................................................................................... 17
Optical isomerism (3.7) ..................................................................................................... 18
Aldehydes and ketones (3.8) .............................................................................................. 19
Carboxylic acids and their derivatives (3.9) ......................................................................... 20
Carboxylic acids and esters (3.9.1) ............................................................................................................................ 20
Acylation (3.9.2) ........................................................................................................................................................ 21
Page 1 of 44
,Aromatic Chemistry (3.10) ................................................................................................. 23
Bonding (3.10.1) ........................................................................................................................................................ 23
Electrophilic substitution (3.10.2) .............................................................................................................................. 24
Amines (3.11) ................................................................................................................... 26
Preparation (3.11.1) ................................................................................................................................................... 26
Base properties (3.11.2) ............................................................................................................................................. 27
Nucleophilic properties (3.11.3) ................................................................................................................................. 27
Polymers (3.12)................................................................................................................. 29
Condensation polymers (3.12.1) ................................................................................................................................ 29
Biodegradability and disposal of polymers (3.12.2) ..................................................................................................... 31
Amino acids, proteins, and DNA (3.13)................................................................................ 32
Amino acids (3.13.1) .................................................................................................................................................. 32
Proteins (3.13.2) ........................................................................................................................................................ 33
Enzymes (3.13.3) ....................................................................................................................................................... 35
DNA (3.13.4) .............................................................................................................................................................. 36
Action of anticancer drugs (3.13.5)............................................................................................................................. 37
Organic synthesis (3.14) .................................................................................................... 38
NMR Spectroscopy (3.15) .................................................................................................. 40
Chromatography (3.16)...................................................................................................... 43
Page 2 of 44
, Introduction to organic chemistry (3.1)
Nomenclature (3.1.1)
- Organic compounds can be represented by:
o Empirical formula – the simplest possible whole number ratio of the different types of
atoms within the compound
o Molecular formula – formula that gives the actual number of atoms of each element in one
molecule
o General formula – shows the number of atoms of each element in a substance which has n
carbon atoms. All the molecules in a homologous series have the same general formula
o Structural formula – shows how the atoms are joined together in a molecule
o Displayed formula – shows all the bonds and atoms in a molecule
o Skeletal formula – uses lines to represent bonds. Each point represents a C atom
- Homologous series = a family of compounds with same general formula and similar chemical
properties
o Characteristics:
• Same general formula
• Same functional group
• Similar chemical properties
- Functional group: nomenclature guidelines:
Functional group Prefix Suffix
Alkane -ane
Alkene -ene
Halogenoalkane Fluoro- / Bromo- /
Chloro- / Iodo-
Alcohol Hydroxy- -ol
Aldehyde -al
Ketone Oxo- -one
Carboxylic acid -oic acid
Nitrile -nitrile
Amine Amino- -amine
Acyl chloride -oyl chloride
Acid anhydride -oic anhydride
Ester -oate
Amide -amide
- Naming priorities:
carboxylic acids > aldehydes > ketones > alcohols > alkenes > halogenoalkanes
Page 3 of 44
