AH CHEMISTRY UNIT 3: Organic Chemistry
3(a) Permeating Aspects of Organic Chemistry
Learning outcomes
(i) Reaction types
Understand what is meant by the following types of reaction in organic chemistry:
 Substitution
 Addition
 Elimination
 Condensation
 Hydrolysis
 Oxidation
 Reduction
(ii) Reaction mechanisms
Understand the following mechanisms of reactions in terms of electron shift:
 Radical substitution
 Electrophilic addition (carbocation intermediate and cyclic ion
intermediate)
 Nucleophilic substitution (SN1 and SN2)
(iii) Physical properties
Understand how the physical properties (melting and boiling points, miscibility with
water) of organic substances can be explained by intermolecular forces.
AH CHEMISTRY UNIT 3: Organic Chemistry
3(b) Systematic organic chemistry
Learning outcomes
(i) Hydrocarbons and halogenoalkanes
1. Understand what is meant by hybridisation and hybrid orbitals.
2. Understand how bonding in alkanes can be described in terms of sp3 hybridisation
and sigma bonding.
3. Understand how a sigma bond is formed.
4. Know what type of reaction alkanes undergo with chlorine and bromine.
5. Understand the mechanism of reaction of alkanes with chlorine and bromine.
6. Understand the three steps involved in an organic chain reaction.
7. Understand how bonding in alkenes can be described in terms of sp2 hybridisation,
sigma and pi bonding.
8. Understand how a pi bond is formed.
9. Understand how alkenes can be prepared in the lab by:
 Dehydration of alcohols using aluminium oxide, concentrated sulphuric acid or
orthophosphoric acid;
 Base-induced elimination of hydrogen halides from monohalogenoalkanes.
10. Understand how Markovnikov’s rule can be used to predict the products formed in
the reaction of alkenes with hydrogen, halogens, hydrogen halides and water.
11. Understand the mechanism involved in addition reactions of alkenes with:
 Halogens;
 Hydrogen halides;
 Water
12. Know how to name halogenoalkanes according to IUPAC rules.
13. Understand how to classify monohalogenoalkanes as primary, secondary or tertiary.
14. Understand how monohalogenoalkanes undergo nucleophilic substitution
reactions.
15. Understand how monohalogenoalkanes undergo elimination reactions.
16. Understand how monohalogenoalkanes react with:
 Alkalis;
 Alcoholic alkoxides;
 Ethanolic cyanide;
 Ammonia.
(ii) Alcohols and Ethers
1. Understand the relative boiling points of alcohols compared to other organic
compounds of comparative relative formula mass and shape.
2. Understand the relationship between chain length and solubility of alcohols.
3. Know how alcohols can be prepared from alkenes.
4. Know how alcohols can be prepared from halogenoalkanes.
5. Know how alcohols (except methanol) are manufactured in industry.
6. Know how alkoxides can be prepared from alcohols.
7. Know how alkenes can be prepared from alcohols.
8. Know how esters can be prepared from alcohols by two different routes – one slow
and one vigorous.
9. Understand what ethers are.
10. Know how to use IUPAC rules to name ethers.
11. Understand the relative boiling points of ethers compared to their isomeric alcohols.
12. Understand the relative solubility in water of ethers with low molecular mass.
13. Understand why exposure of ethers to air can be dangerous.
14. Know how ethers can be prepared from halogenoalkanes.
15. Understand why ethers make effective solvents.
(iii) Aldehydes, Ketones and Carboxylic Acids
1. Understand the relative boiling points of aldehydes, ketones and carboxylic acids
compared to the corresponding alkanes.
2. Understand the relative boiling points of aldehydes, ketones and carboxylic acids
compared to the corresponding alcohols.
3. Understand the relative solubility in water of aldehydes, ketones and carboxylic
acids with low molecular mass.
4. Understand the reactions involved in distinguishing aldehydes and ketones using
Fehling’s solution or Tollens’ reagent.
5. Know how primary and secondary alcohols can be prepared from aldehydes and
ketones.
6. Know how cyanohydrins can be prepared from aldehydes and ketones.
7. Know how hydroxyl carboxylic acids can be prepared from cyanohydrins.
8. Know how hydrozones and 2,4-dinitrophenylhydrozones can be prepared from
aldehydes and ketones.
9. Understand how unknown aldehydes and ketones can be identified by melting
point determination.
10. Understand the general relative reactivity of aldehydes compared to ketones.
11. Understand the formation of dimers in pure carboxylic acids.
12. Understand the relative stability of the carboxylate ion in solutions of carboxylic
acids.
13. Know how carboxylic acids can be prepared from alcohols.
14. Know how carboxylic acids can be prepared from nitriles, esters or amides.
15. Know how salts can be prepared from carboxylic acids.
16. Know how esters can be prepared from carboxylic acids.
17. Know how amides can be prepared from carboxylic acids.
18. Know how alcohols can be prepared from carboxylic acids.
(iv) Amines
1. Know how to use IUPAC rules to name amines.
2. Understand how to classify amines as primary, secondary or tertiary.
3. Understand the relative boiling points of primary and secondary amines compared
to their isomeric tertiary amine or corresponding alkane with comparable relative
formula mass.
4. Understand the relative solubility of amines with low molecular mass.
5. Understand why amines are classified as weak bases.
6. Know how salts can be prepared from amines.
(v) Aromatics
1. Understand the types of bonding that exist in aromatic compounds.
2. Understand the relative stability of benzene.
3. Know the characteristic type of reaction of benzene.
4. Understand specific examples of this characteristic type of reaction, including:
- chlorination and bromination
- nitration
- sulphonation
- alkylation
5. Understand the relative acidity of phenol compared to aliphatic alcohols.
6. Understand the relative alkalinity of aminobenzene (aniline) compared to aliphatic
amines.
AH CHEMISTRY UNIT 3: Organic Chemistry
3(c) Stereoisomerism
Learning outcomes
1.
2.
3.
4.
Understand what stereoisomers are.
Understand what geometric isomers are.
Know how to classify geometric isomers as cis or trans.
Understand how cis and trans geometric isomers compare to each other in terms
of their physical and chemical properties.
5. Understand what optical isomers are.
6. Understand when optical isomerism can arise.
7. Understand how optical isomers compare to each other in terms of their physical
and chemical properties.
8. Understand why optical isomers can be described as being “optically active”.
9. Understand how to prepare an optically inactive mixture of optical isomers.
10. Understand the make up of biological systems in terms of the optical isomers that
are usually present.
AH CHEMISTRY UNIT 3: Organic Chemistry
3(d) Structural Analysis
Learning outcomes
(i) Elemental micro-analysis and mass spectroscopy
1. Understand how elemental micro-analysis (and its results) can be used to
determine the empirical formula of an organic compound containing C, H, O
and N.
2. Know what mass spectroscopy is used for.
3. Understand how a conventional mass spectrometer works.
4. Understand how to interpret mass spectra to obtain information about an
organic compound.
(ii) Infra-red and nuclear magnetic resonance spectroscopy and X-ray crystallography
1. Know what infra-red spectroscopy is used for.
2. Understand the effect of infra-red radiation on molecules.
3. Understand how the technique of infra-red spectroscopy works.
4. Understand how to interpret infra-red spectra.
5. Know what nuclear magnetic resonance spectroscopy is used for.
6. Understand how the technique of nuclear magnetic resonance spectroscopy
works.
7. Understand how to interpret nuclear magnetic resonance spectra.
8. Know the name of the standard reference substance used in NMR spectroscopy.
9. Know what X-ray crystallography is used for.
10. Understand how the technique of X-ray crystallography works.
11. Understand how to interpret electron density maps.
12. Understand why hydrogen atoms are not easily detected by X-rays.
AH CHEMISTRY UNIT 3: Organic Chemistry
3(e) Medicines
Learning outcomes
1.
2.
3.
4.
5.
6.
7.
8.
Know what drugs are.
Know what medicines are.
Understand in general terms how the first medicines were developed.
Understand in general terms how medicines function.
Know what a pharmacophore is.
Understand how a pharmacophore functions.
Understand how a pharmacophore can be identified.
Understand what agonists and antagonists are.