Organic Chemistry

Module summary

Module code: CHEM1030
Level: 4
Credits: 15
School: Engineering and Science
Department: Science
Module Coordinator(s): Kevin Lam

Specification

Aims

The module is designed to give the student an understanding of the basic principles of organic chemistry. To achieve this, students will study the structure and bonding of organic compounds and the mechanisms of organic reactions. The application of these concepts will be illustrated in the study of the chemistry of hydrocarbons and simple mono-functional group compounds.

Learning outcomes

On successful completion of this module a student will be able to:
1. Describe the influences of structure and bonding on the physical properties and isomerism of organic compounds.
2. Use and interpret organic reaction mechanisms in the reactions of hydrocarbons and simple mono-functional group compounds.
3. Describe and explain the reactions of hydrocarbons in relation to their structure and
mechanisms of reaction.
4. Describe and explain the reactions of simple mono-functional group compounds in relation to their structure and mechanisms of reaction.

Indicative content

1 Structure and bonding
Bonding: sp3, sp2 and sp hybridisation of carbon, - and - bonds, delocalisation,
intermolecular forces.
Structure: bond angles, bond length, shapes of molecules, structural and geometric isomerism.
Classification: alkanes, alkenes, alkynes, arenes, alcohols, phenols, ethers, aldehydes, ketones,
carboxylic acids, esters, acid anhydrides, acid halides, amines, amides, cyanides (nitriles),
haloalkanes and haloarenes.
Physical Properties: homologous series, trends in boiling points and solubilities related to
structure and intermolecular forces.
Experimental methods related to physical properties: melting points, spectra (ir, uv, mass, nmr),
purification (distillation, crystallisation, chromatography- tlc, column, glc).

2 Organic reaction mechanisms
Types of reactions: addition, substitution, elimination, rearrangement, condensation.
Types of reagent: electrophile, nucleophile, radical, acid, base.
Mechanisms: use of curly arrows, one and two-electron movements, bond polarisation,
electronegativity, homolysis, heterolysis, energy profiles, reaction coordinate, transition state,
reaction intermediate, activation energy.

3 Reactions of hydrocarbons
Alkanes: sources, halogenation, combustion, sulphonation, nitration, pyrolysis, radical stabilities,
mechanism of radical substitution, uses as fuels and sources of industrial materials.
Alkenes: electrophilic addition reactions, hydration, oxymercuration, hydroboration, addition of
halogens and hydrogen halides, oxidation with MnO4- and OsO4- , peroxidation, hydrogenation,
polymerisation, carbocation stabilities, direction of addition, ozonolysis, uses as sources of
industrial materials.
Alkynes: hydration, hydrogenation, alkynide formation of terminal alkynes

4 Reactions of simple mono-functional group compounds
Haloalkanes: nucleophilic substitution reactions with H2O, OH-, CN-, NH3 and RO-; SN1 and SN2
mechanism, stereochemical consequences, elimination reactions, direction of elimination, E1 and
E2 mechanisms, elimination vs substitution, Grignard reagent formation.
Haloarenes: reactivity in comparison to haloalkanes
Alcohols and phenols: acidity, reaction with sodium, reaction with hydrogen halides and
phosphorus halides, oxidation, haloform reaction, dehydration, halogenation of phenols.
Aldehydes and ketones: oxidation, haloform reaction, reduction, condensation with ammonia
derivatives, reaction with Grignard reagents.
Carboxylic acids: acid/base reactions, esterification, acid halides, acid anhydrides, alpha-
halogenation.
Amines: acid/base reactions, amide formation, diazotisation, coupling of diazonium compounds,
Hofmann elimination.