Doc Brown's
Advanced A Level Chemistry
Revision Study Notes
for
pre-university
Organic Chemistry
(re-edit)
email doc
brown - comments - query?
ADVANCED ORGANIC CHEMISTRY TOPICS
(pre-university)
Revision study notes and for researching information
|
PART 0 An Advanced Introduction to Organic Chemistry
An Advanced Introduction to pre-university organic chemistry - history,
bonding, variety and complexity
PART 1 The chemistry of ALKANES and OIL
for Advanced A
Level Organic Chemistry
1.0
The chemistry of ALKANES and the petrochemical
industry
revision notes INDEX
1.1
The Molecular Structure and Nomenclature of Alkanes
1.2
Fractional distillation of crude
oil and uses of products
1.3
Modification of alkanes by
cracking, isomerisation and reforming
1.4
Complete and incomplete
combustion of alkanes and environmental pollution
1.5
Modification of hydrocarbon fuel mixtures, alternative fuels
and global warming
1.6
Chlorination and bromination of
alkanes, reaction mechanisms and uses of products
Combined
multiple choice and type in name quiz on the structure
and naming of alkanes
Matching pair quiz on hydrocarbon structure
The following notes have
basic reaction conditions, reagents and general equations as well as
detailed notes on the mechanisms indicated and where written
before the alkanes notes.
Free radical
chlorination/bromination to give halogenoalkanes (haloalkanes,
alkyl halides)
Free radical mechanism for cracking
hydrocarbons to
give shorter alkanes and alkenes
Ionic mechanism for cracking
hydrocarbons
TOP OF PAGE and
INDEXES
|
PART 2 The chemistry of ALKENES for Advanced
A Level Organic Chemistry
2.0
INDEX of
ALL advanced revision notes on ALKENES
2.1
Revision notes on the structure and naming of ALKENES (including
cyclo..), including many isomers
2.2
Sources, synthesis, physical
properties and combustion of alkenes
2.3
Bonding in alkenes, reactivity compared to alkanes,
electrophilic addition reaction with hydrogen halides
2.4
The electrophilic addition reaction
of alkenes with halogens (non-aqueous and aqueous conditions)
2.5
Reaction of alkenes with
hydrogen - uses of hydrogenation, structure and properties of oils
and fats
2.6
The reaction of alkenes with steam -
addition of water - synthesis of alcohols and the reaction of
alkenes with concentrated sulfuric acid
2.7
The reaction of alkenes with aqueous
potassium manganate(VII) - formation of diol alcohols
2.8
The
polymerisation of alkenes to
form addition polymers - structure, properties, uses of
poly(alkene) polymers
2.9
Uses of alkenes and
occurrence of the alkene functional group in biological molecules
see also
E/Z
stereoisomerism in alkenes
and
Combined multiple choice and type in name quiz on the structure and naming of
alkenes
(Since these mechanism notes
were written, I've completed the set of notes above on the general chemistry
of alkenes, including essential details of all these mechanisms).
Electrophilic addition of
hydrogen bromide
[HBr(conc. aq)
and HBr(g/non-polar solvent)] to form
halogenoalkanes
Electrophilic addition of
bromine with pure
bromine or in non-polar solvent
(non-aqueous Br2(l/solvent)) to give
dibromoalkanes AND addition using bromine water [aqueous Br2(aq)]
to give bromo-alcohols
Electrophilic addition of
sulphuric acid AND electrophilic
addition of water
[acid catalyst] to form alcohols
Free radical polymerisation
to give poly(alkene) polymers e.g. ethene ==> poly(ethene)
Hydrogenation to give
saturated alkanes
TOP OF PAGE and
INDEXES
|
PART 3 The chemistry of HALOGENOALKANES (HALOALKANES)
3.0
INDEX of
ALL revision notes on HALOGENOALKANES (haloalkanes)
3.1
Molecular Structure and Nomenclature of
Halogenoalkanes (haloalkanes)
3.2
Laboratory synthesis & industrial manufacture of halogenoalkanes
(haloalkanes) from alcohols, alkanes, alkenes
3.3
Reactivity trends of halogenoalkanes - introduction to their nucleophilic
substitution reactions, the substitution reaction between halogenoalkanes (haloalkanes)
& water, experiments with silver nitrate solution
3.4
The
substitution reaction of halogenoalkanes (haloalkanes) with sodium/potassium hydroxide to
give alcohols
3.5
The
nucleophilic substitution reaction between halogenoalkanes (haloalkanes) and potassium cyanide
and hydrolysis of nitriles to carboxylic acids
3.6
The
substitution reaction between halogenoalkanes (haloalkanes) and ammonia and amines
forming primary, secondary and tertiary amines
3.7
The elimination reactions of
halogenoalkanes (haloalkanes) with potassium hydroxide to give alkenes
3.8
The
physical properties, hazards and uses of
halogenoalkanes (haloalkanes)
3.9
The chemistry of ozone depletion and how this environmental problem
was solved
(Since these mechanism notes
were written, I've completed the set of notes above on the general chemistry
of haloalkanes, including essential details of all these mechanisms)
Nucleophilic substitution by water/hydroxide ion
[SN1 or SN2, hydrolysis to
give alcohols]
with extra notes on
kinetics, rds, molecularity, rate expression, activated complex etc.
Nucleophilic
substitution by cyanide ion to give a nitrile
[SN1 or SN2]
Nucleophilic
substitution by ammonia/primary amine to give primary/secondary
amines etc.
[SN1 or SN2]
Elimination of
hydrogen bromide to form alkenes [E1 and E2]
Free radical
chlorination/bromination to give halogenoalkanes (haloalkanes,
alkyl halides)
TOP OF PAGE and
INDEXES
|
PART 4 The chemistry of ALCOHOLS (mention of
ethers)
for A Level Organic Chemistry
4.0
INDEX of all revision notes on
ALCOHOLS (and mention of ethers)
4.1
Revision notes on the structure and naming
(nomenclature) of aliphatic
ALCOHOLS, ETHERS, epoxy-alkanes (parts 1-2), including isomers
4.2
The laboratory synthesis and manufacture of
alcohols
4.3
Physical properties
(boiling points, solubility) and intermolecular forces
4.4
Combustion of alcohols,
enthalpies of combustion and use as fuels
4.5
Controlled oxidation
of alcohols with selected oxidising
agents
4.6
Miscellaneous reactions with: (1) metallic sodium, (2) acid
chlorides, (iii) carboxylic acids
4.7
Halogenation with hydrogen halides: Conversion of
alcohols to
halogenoalkanes (haloalkanes)
4.8
Chemical tests for alcohols
4.9
Examples of uses
of alcohols
(Since these mechanism notes
were written, I've completed the set of notes above on the general chemistry
of alcohols, including essential details of all these mechanisms)
Conversion of an alcohol to a halogenoalkane
Elimination of water from an
alcohol to give an alkene [acid catalysed, E1 and E2]
TOP OF PAGE and
INDEXES
|
PART 5 The chemistry of ALDEHYDES and KETONES
for Advanced A Level Organic Chemistry
5.0
INDEX of
ALL revision notes on ALDEHYDES and KETONES
5.1
Revision notes on the
Structure and Naming of Aldehydes and Ketones
(Also includes an introduction as to how
to write and display aldehyde and ketone formulae including isomers)
5.2
Physical properties of aldehydes and
ketones and intermolecular bonding forces
5.3
Methods of preparing aldehydes and
ketones
5.4
The structure and reactivity of
aldehydes and ketones and nucleophilic addition of hydrogen cyanide
(also includes the hydrolysis of the
resulting nitriles to carboxylic acids)
5.5
The reduction of aldehydes and
ketones with NaBH4
and LiAlH4 and
reduction of nitriles
5.6
Examples of addition - elimination
condensation reactions of aldehydes and ketones including with
2,4-dinitrophenylhydrazine for identification
5.7
The oxidation of aldehydes and
ketones, link with chemical tests and the iodoform reaction
5.8
The uses of aldehydes and ketones
and their occurrence in nature
(Since these mechanism notes
were written, I've completed the set of notes above on the general chemistry
of aldehydes and ketones, including essential details of all these mechanisms)
Nucleophilic addition of
hydrogen cyanide to form a hydroxy-nitrile
Addition of hydrogen -
reduction with LiAlH4 or NaBH4
to give alcohols
The iodination of ketones e.g.
a 2-one like propanone (a methyl ketone) to give iodo-ketones
TOP OF PAGE and
INDEXES
|
PART 6 The chemistry of CARBOXYLIC ACIDS and DERIVATIVES
e.g. substituted
molecules, esters, amides, acyl chlorides etc. for
Advanced A Level Organic Chemistry
6.0
INDEX of all revision notes on
CARBOXYLIC ACIDS and DERIVATIVES
6.1
Structure and naming of CARBOXYLIC ACIDS and DERIVATIVES,
including nomenclature of isomers
6.1
Structure & naming of
carboxylic acids and derivatives
6.2
Physical properties of
carboxylic acids - trends discussed & explained (mpts, bpts,
solubility, odours!)
6.3
Synthetic routes & methods of preparing
carboxylic acids
6.4
The weakly acidic nature and general reactions of carboxylic acids acting as
acids
6.5
Selective reduction of carboxylic acids - use of products in
organic synthesis
6.6
The chlorination/bromination of carboxylic acids,
use of products in organic synthesis
6.7
Preparation & reactions of acid chlorides with water, alcohols,
ammonia, amines & mechanisms
6.8
Esters
- preparation, reactions including hydrolysis and
transesterification
6.9
Natural esters - triglyceride fats and oils,
manufacture of margarine and biodiesel
6.10
The manufacture, molecular structure, properties and uses of
polyesters
6.11
Amides
- molecular structure, physical properties, preparations, reactions, brief mention of
polyamides
6.12
Nitriles - molecular
structure, preparations and reactions
6.13
Amino acids - molecular
structure, preparation and reactions - two functional group
chemistries
6.14
More on the uses of carboxylic acids
and derivatives and occurrence in
nature and pharmaceuticals
(Since these mechanism notes
were written, I've completed the set of notes above on the general chemistry
of carboxylic acids and derivatives, including essential details of all these mechanisms)
Hydrolysis of acid chlorides with water
to give a carboxylic acid
Esterification of acid
chlorides with alcohols
to give an ester
Amide formation from reaction
of acid chlorides with ammonia
or primary amines
TOP OF PAGE and
INDEXES
|
PART 7
The chemistry of AROMATIC COMPOUNDS
for Advanced A Level Organic Chemistry
Arenes, phenols, haloaromatics, aromatic amines, aromatic carboxylic acids etc.
for Advanced A Level Organic Chemistry
7.0
INDEX of all AROMATIC COMPOUND chemistry
revision notes
7.1
The Structure
& Naming of Aromatic Compounds,
including nomenclature of isomers
(7.1 also includes an extensive introduction as to how
to write and display aromatic formulae including isomers - lots of examples)
7.2
Proof of the structure of benzene, aromaticity
and electrophilic reactivity in arenes
7.3
Sources and synthesis of arenes and physical properties of arene aromatic
hydrocarbons
7.4
Free radical addition reactions
of benzene and methylbenzene with hydrogen and chlorination of the
methyl group of methylbenzene
7.5
Electrophilic substitution -
nitration of benzene and methylbenzene, properties and uses of
nitro-aromatics
7.6
Electrophilic substitution - ring
halogenation of benzene & methylbenzene, properties & uses of aryl
halides
7.7
Electrophilic substitution -
ring sulfonation of arenes, properties & uses of
sulfonic acids
7.8
Electrophilic substitution -
acylation of arenes, properties & uses of
aromatic ketones and aromatic aldehydes
7.9
The physical and chemical
properties of phenol and some of its derivatives and their uses
7.10
Physical & chemical
properties of phenylamine, selected derivatives including diazonium
ions and dyes
7.11
The physical and chemical
properties of benzoic acid and selected derivatives
7.12
The structure, properties and uses of
polyesters and polyamides involving aromatic monomers
7.13
Examples of aromatic compounds from the
pharmaceutical industry and those found in natural
products
7.14
The orientation of products
on putting a 2nd substituent into a monosubstituted benzene derivative
(aspects of 7.14 go beyond what
is normally required in pre-university chemistry courses)
The following notes have
basic reaction conditions, reagents and general equations as well as
detailed notes on the mechanisms indicated and were written before
the above notes on aromatic chemistry.
Nitration to give
nitro-aromatics like nitrobenzene
Chlorination to
chloro-aromatics like chlorobenzene
Alkylation to give
alkyl-aromatics like methylbenzene
[Friedel-Crafts reaction]
Acylation to give aromatic
ketones
[Friedel-Crafts reaction]
Sulfonation to
give a sulfonic acid like benzenesulfonic
acid
TOP OF PAGE and
INDEXES
|
PART 8 ORGANIC NITROGEN COMPOUNDS
for Advanced A Level Organic Chemistry
Amines,
amides, amino acids etc. for Advanced A Level
Organic Chemistry
8.0
INDEX of all ORGANIC NITROGEN COMPOUND chemistry pages
8.1
Structure, Classification
& Naming of
Organic Nitrogen Compounds,
including nomenclature of isomers
8.2
The
structure, classification and physical properties of aliphatic amines
8.3
Methods of synthesising amines
(aliphatic and aromatic), includes reaction of amines with halogenoalkanes
8.4
Acid-base chemistry of aliphatic
amines, their comparative strength as bases and reactions with acids
8.5
The
chemistry of amides e.g. reaction with acid chlorides and acid anhydrides,
polyamides - formation, structure, properties and uses
8.6
Complexing reactions
- primary aliphatic amines with d-block metal ions
(transition metal complexes)
8.7
Amine
bases and the hydrogen bonding in DNA and RNA
8.8
LINKS to all my notes on amino acids, peptides, polypeptides and types
of proteins
See also other
pages involving organonitrogen compounds
(I have not repeated everything in the above pages!)
Section 6.11
AMIDES
- molecular structure, preparations and reactions, brief mention of
polyamides
Section 6.12
The chemistry of NITRILES - molecular
structure, preparations and reactions
Section 6.13
Amino acids - molecular
structure, preparation and reactions - two functional group
Section 6.14
More on the uses of carboxylic acids
and derivatives and occurrence in
nature
Section 7.10
The
chemistry of AROMATIC AMINES including preparation of phenylamine,
acylation, electrophilic substitution and azo dyes
and
Amino
acids as a case study of R/S isomerism
The following notes have
basic reaction conditions, reagents and general equations as well as
notes on the mechanisms indicated and were written before
the above notes on the chemistry of organic nitrogen compounds.
Nucleophilic
substitution by cyanide ion to give a nitrile
[SN1 or SN2]
Nucleophilic
substitution by ammonia/primary amine to give primary/secondary
amines etc.
[SN1 or SN2]
Nucleophilic addition of
hydrogen cyanide to form a hydroxy-nitrile
Amide formation from reaction
of acid chlorides with ammonia
or primary amines
Nitration of arenes to give
nitro-aromatics like nitrobenzene
|
PART 9 FUNCTIONAL GROUP & HOMOLOGOUS SERIES SUMMARY
(includes an
ADVANCED introduction to organic chemistry and its history)
A summary of
homologous series, functional group names and structure in Organic Chemistry |
TOP OF PAGE and
INDEXES
PART 10 SUMMARY NOTES on ORGANIC CHEMISTRY MECHANISMS
and ORGANIC SYNTHESIS ROUTES
for Advanced A Level
Organic Chemistry
PART 10 An
Introduction to organic chemical reaction mechanisms and technical
terms explained
Also includes a mechanism index
Organic Synthesis - MECHANISMS INDEX
Part 10.2
ALKANES - an introduction to their chemistry
Free radical
chlorination/bromination to give halogenoalkanes (haloalkanes,
alkyl halides)
Free radical mechanism for cracking
hydrocarbons to
give shorter alkanes and alkenes
Ionic mechanism for cracking
hydrocarbons
Part 10.3 ALKENES
- introduction to their chemistry
Electrophilic addition of
hydrogen bromide
[HBr(conc. aq)
and HBr(g/non-polar solvent)] to form
halogenoalkanes
Electrophilic addition of
bromine with pure
bromine or in non-polar solvent
(non-aqueous Br2(l/solvent)) to give
dibromoalkanes AND addition using bromine water [aqueous Br2(aq)]
to give bromo-alcohols
Electrophilic addition of
sulfuric acid AND electrophilic
addition of water
[acid catalyst] to form alcohols
Free radical polymerisation
to give poly(alkene) polymers e.g. ethene ==> poly(ethene)
Hydrogenation to give
saturated alkanes
Part 10.4 HALOGENOALKANES
- introduction to
the chemistry of haloalkanes/alkyl halides
Nucleophilic substitution by water/hydroxide ion
[SN1 or SN2, hydrolysis to
give alcohols]
with extra notes on
kinetics, rds, molecularity, rate expression, activated complex etc.
Nucleophilic
substitution by cyanide ion to give a nitrile
[SN1 or SN2]
Nucleophilic
substitution by ammonia/primary amine to give primary/secondary
amines etc.
[SN1 or SN2]
Elimination of
hydrogen bromide to form alkenes [E1 and E2]
Part 10.5 ALCOHOLS
- introduction to their chemistry
Conversion of an alcohol to a halogenoalkane
Elimination of water from an
alcohol to give an alkene [acid catalysed, E1 and E2]
Part
10.6 Carbonyl compounds - ALDEHYDES and
KETONES - introduction
to their chemistry
Nucleophilic addition of
hydrogen cyanide to form a hydroxy-nitrile
Addition of hydrogen -
reduction with LiAlH4 or NaBH4
to give alcohols
The iodination of ketones e.g.
a 2-one like propanone (a methyl ketone) to give iodo-ketones
Part
10.7 Carboxylic Acids and ACID CHLORIDES
- introduction -
all nucleophilic addition-elimination reactions
Hydrolysis of acid chlorides with water
to give a carboxylic acid
Esterification of acid
chlorides with alcohols
to give an ester
Amide formation from reaction
of acid chlorides with ammonia
or primary amines
Part 10.8 AROMATIC HYDROCARBONS
- introduction to arene electrophilic substitutions
Nitration to give
nitro-aromatics like nitrobenzene
Chlorination to
chloro-aromatics like chlorobenzene
Alkylation to give
alkyl-aromatics like methylbenzene
[Friedel-Crafts reaction]
Acylation to give aromatic
ketones
[Friedel-Crafts reaction]
Sulphonation/sulfonation to
give a sulphonic/sulfonic acid like benzenesulphonic
acid/benzenesulfonic acid
The orientation of products in
aromatic substitution (2,4,6 or 3,5 positions, ortho, para & meta
substitution products)
TOP OF PAGE and
INDEXES
|
PART 11 QUALITATIVE TESTS
for Advanced A Level Organic Chemistry
Qualitative Analysis Tests for organic functional groups
notes
(use alphabetical index) |
PART 12 A summary of ORGANIC REDOX REACTIONS
Detailed notes
on redox
synthesis reactions for Advanced A Level Organic
Chemistry
Revision notes on Oxidation and reduction synthesis
reactions, fuel cells etc. (sub-indexes of sections) |
PART 13 ORGANIC MOLECULE SHAPES and BOND ANGLES
for Advanced A Level Organic Chemistry
Revision notes on molecule shapes - section added on the bond angles of organic molecules |
PART 14
STEREOCHEMISTRY and ISOMERISM in ORGANIC MOLECULES
Notes on types of isomerism and aspects of
stereochemistry
14.0
INDEX of isomerism
& stereochemistry of organic compounds
notes
14.1
General introduction and definition
of isomerism, structural isomerism - chain, positional, functional
group and tautomerism types of isomerism
14.2
STEREOISOMERISM general definition, E/Z (geometric/geometrical
cis/trans) isomerism
14.3
Stereoisomerism - R/S Optical
Isomerism examples and chiral auxiliary synthesis
Other sections with stereochemical connections
14.4
Protein-enzyme structure, function
and inhibition
14.5
Protein
analysis & synthesis AND combinatorial chemistry and
autosynthesis
14.6
Stereoregular polymers -
isotactic/atactic/syndiotactic poly(propene)
14.7
Isomers
given a molecular formula
TOP OF PAGE and
INDEXES
|
Part 15 Spectroscopy
- a means of investigating molecular structure
15.0
Index of all spectroscopy
pages and introduction
15.1
Index of mass spectroscopy notes -
examples of mass spectrometry of organic
compounds
15.2
Index of infrared spectroscopy notes - analysis of infrared spectra
of organic compounds
15.3
Index of nuclear
magnetic resonance spectroscopy
1H NMR spectra of organic
compounds
15.4
Index of nuclear
magnetic resonance spectroscopy
13C NMR spectra of organic
compounds
15.5
Index of emission and absorption
spectroscopy including colorimetry and flame photometry
|
TOP OF PAGE and
INDEXES
Other Notes Links
maybe useful
for Advanced Level Organic Chemistry
NANOCHEMISTRY index - nanoscience nanoparticles fullerenes carbon nanotubes
SMART MATERIALS index which
obviously overlaps with nanomaterials
Formulation chemistry
Uses of chemicals, 220+ examples in alphabetical order, GCSE orientated, but
still useful quotes
TOP OF PAGE and
INDEXES
|
Good memories of 6th form teaching at Whitby
Community College (1978-2003)
(now Caedmon College, Whitby, North Yorkshire,
England)
Website content © Dr
Phil Brown 2000+. All copyrights reserved on revision notes, images,
quizzes, worksheets etc. Copying of Doc Brown's pre-university
advanced level chemistry website material is NOT
permitted. Exam revision summaries & references to science course specifications
are unofficial.
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