Doc Brown's Advanced A Level Chemistry Exam Revision Study Notes for pre-university/college Organic Chemistry Courses

[Author ©  Dr Phil Brown PhD: Doc Brown's exam revision notes suitable for students of advanced pre-university/college A-level chemistry courses: INDEX of organic advanced A-level chemistry revision Notes [index updated RE-EDIT]

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ADVANCED LEVEL ORGANIC CHEMISTRY TOPICS (pre-university/college)

Revision study notes and for researching information

Help links for OCR advanced level chemistry A (AS and A level courses)

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

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

More on the uses of plastics, issues with using plastics, solutions and recycling methods

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 Br_2(l/solvent)) to give dibromoalkanes AND addition using bromine water [aqueous Br_2(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

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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

(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 [S_N1 or S_N2, 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 [S_N1 or S_N2]

Nucleophilic substitution by ammonia/primary amine to give primary/secondary amines etc. [S_N1 or S_N2]

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]

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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

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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

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, uses

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

Electrophilic substitution - alkylation of arenes to give other arenes

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

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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), including reaction of amines with halogenoalkanes and reduction of nitriles

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 [S_N1 or S_N2]

Nucleophilic substitution by ammonia/primary amine to give primary/secondary amines etc. [S_N1 or S_N2]

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

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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 Br_2(l/solvent)) to give dibromoalkanes AND addition using bromine water [aqueous Br_2(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 [S_N1 or S_N2, 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 [S_N1 or S_N2]

Nucleophilic substitution by ammonia/primary amine to give primary/secondary amines etc. [S_N1 or S_N2]

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 which can be hydrolysed to give a carboxylic acid

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]

Sulfonation/sulfonation to give a sulfonic/sulfonic acid like benzenesulfonic acid/benzenesulfonic acid

The orientation of products in aromatic substitution (2,4,6 or 3,5 positions, ortho, para & meta substitution products)

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PART 11 QUALITATIVE TESTS for Advanced A Level Organic Chemistry

Qualitative Analysis Tests for organic functional groups notes (use alphabetical index)

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)

for Advanced A Level Organic Chemistry

Revision notes on molecule shapes - section added on the bond angles of organic molecules

Notes on types of isomerism and aspects of stereochemistry

14.0 INDEX of isomerism and 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 - names and structures for a given molecular formula

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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

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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

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Good memories of 6th form teaching at Whitby Community College (1978-2003)

(now Caedmon College, Whitby, North Yorkshire, England)

For advanced level pre-university/college chemistry

 The chemistry of ALKANES and the petrochemical industry

 The chemistry of CARBOXYLIC ACIDS, ESTERS and other derivatives

 The chemistry of ORGANIC-NITROGEN compounds

 

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