This module provides learners with the foundation of knowledge required to be able to understand the chemical behaviour of organic molecules. It deals with the identification of functional groups, their chemical behaviour towards different reagents, and the description of the course of reactions in terms of electronic mechanism.

Knowledge

1. describe the geometry of common structures using MO and hybridisation descriptions;
2. recognise and draw enantiomers, diastereoisomers and E/Z (cis/trans) isomers;
3. state and use conventions for structural representation, including stereochemistry;
4. identify and draw common functional groups;
5. describe reactions  in terms of overall change (substitution, elimination, addition), electron-based processes (homolytic, heterolytic, pericyclic), and electron availability (nucleophile, electrophile);
6. describe the general characteristics and reactivity of a range of saturated compounds;
7. describe S_N1, S_N2, E1 and E2 reactions;
8. use curly arrows in the context of reaction mechanisms.

Understanding

1. understand the gemoetry of common structures using MO and hybridisation schemes;
2. explain the principal factors determining molecular shape, including the conformation of alkanes and cyclohexane;
3. draw and explain the conformations of simple hydrocarbons;
4. use the concept of double bond equivalence;
5. use the concept of resonance to discuss the stability of typical species;
6. explain the terms transition state, intermediate, carbocation, carbanion, radical;
7. relate the major reaction types to molecular structure of appropriate functional groups;
8. understand reactions in terms of overall change (substitution, elimination, addition), electron-based processes (homolytic, heterolytic, pericyclic), and electron availability (nucleophile, electrophile);
9. predict the mechanistic course of a reaction by analysis of substrate structure and reaction conditions.

22 1-hour lectures, 27 (9 x 3) hours of laboratory work, 11 1-hour problem solving classes linked to 2 1-hour coursework assignments, 4 1-hour tutorials

On completion of this module, students will be able to:

1. link theory and experimental practice in synthetic procedures and in identification of substances;
2. apply the fundamentals of organic chemistry to a range of situations, including some extension to previously unseen cases;
3. use the ‘arrow’ convention to describe bond making/breaking in known and unseen reactions;
4. understand and use the conventions for representation of molecular structures;
5. set up laboratory apparatus for handling organic compounds and carry out a range of preparative and qualitative analysis of typical organic compounds;
6. apply logical thinking to solve simple problems in structure determination and reaction mechanism.

Written coursework and examinations will comprise problems based on lecture material which are extended to previously unseen molecules and reactions to enable a student to demonstrate achievement of a combination of knowledge, understanding and intellectual learning outcomes.  Learning outcomes relating to chemistry-specific practical skills will be assessed through laboratory work.

Organic structure and bonding (Autumn semester)

Structural notations.

Bonding: electron counting, resonance structures, hybridization, molecular shape, bond lengths and angles; covalent and van der Waals radii.

Alkanes: nomenclature / IUPAC rules, conformation.

Alkenes: structure and isomerism.

Reaction classification – homolytic, heterolytic, pericyclic processes. Use of arrows to represent electron movements.

Reactive intermediates – carbenium ions, carbanions, carbon radicals; ease of formation. Nucleophiles and electrophiles. Inductive effects. Delocalisation of pi-electrons – resonance and representation of resonance.

Chemical equilibria.

Energetics – energy diagrams, transition states, intermediates, radical reactions.

Acids and Bases: pH, pK_a (inc. Henderson-Hasselbach equation), mechanism of acid-base reactions.

Hammond postulate, transition states, intermediates.

Stereoisomerism: R/S rules, Fischer and Newman projections, enantiomers and diastereomers.

Conformational equilibria of ethane, butane and cyclohexane; syn and antiperiplanar orientations.

 Introduction to functional group chemistry (Spring semester)

Alcohols and Thiols: nomenclature, physical properties, acidity, basicity, formation and use.

Ethers and Sulfides: nomenclature, physical properties, formation, cleavage.

Amines and Ammonium Salts: nomenclature, structure, physical properties, spectroscopy, basicity and acidity, alkylation.

Alkyl Halides: nomenclature, physical properties, formation, uses, substitution and elimination reactions.

Organometallic reagents – organolithium and Grignard reagents: formation, protonolysis.

S_N2: rate law and mechanism, stereochemistry, effect of alkyl halide, nucleophilicity, leaving group.

E2: rate law and mechanism, leaving group, D isotope effects, stereochemistry, regioselectivity, competition with S_N2.

S_N1 and E1: rate law and mechanism, competition, reactivity, stereochemistry.

Reactions of Alkyl Halides: competition between substitution and elimination, equilibrium, reaction rates.

Reactions of Alcohols and Thiols: dehydration, reaction with HX, formation of ethers and bromides .

Sulfonate Esters: structure, formation, reactivity, E2, alkylation.

Laboratory work (Autumn and Spring semesters)

Experiments to practice basic manipulations in organic chemistry.

Preparations of typical crystalline solids, e.g. acetanilide, and the associated work-up and purification procedures.

Isolation of a natural organic compound on a small scale – trimyristin.

Small-scale experiments to illustrate the properties of the major functional groups, and the use of these methods and IR spectroscopy to identify unknown compounds.

Organic Chemistry, 5^th Ed, M Loudon, Roberts & Co

Please see Essential Reading List.