Aims

To equip students with the necessary knowledge and understanding for them to study organic chemistry at Stage 4; to further enhance the students’ knowledge of the chemistry of aldehydes, ketones, esters, amides and related species; to allow students to design syntheses of compounds containing carbonyl groups; to illustrate the rich and diverse chemistry of the carbonyl group and to show how this can be logically predicted; to introduce the concept of retrosynthetic analysis; to show how the chemistry of the carbonyl unit can be used in total syntheses. To show the importance of carbonyl reactions in enzyme chemistry. To highlight the use of organo-element compounds in the synthesis and reactions of carbonyl compounds.

Outline Of Syllabus

Synthesis of Carbonoyls
Dr DA Fulton

Oxidation of alcohols; chromium (Jones, PCC, PDC), ruthenium (TPAP), Swern, hypervalent iodine and MnO2.
Selective Reductions
Oxidative cleavage of C=C; ozonolysis
Addition of hydrides and carbanions; reaction with carboxylic acids, esters, imines and Weinreb amides
Dithianes (unpolung), Benzoin condensation and MPV reaction

Nucleophilic addition to C=O
Dr MJ Hall

General mechanisms for nucleophilic attack on C=O and C=N
Nucelophilic attack of organometallics; synthesis of organometallics and selectivity
Conjugate additions; hard vs soft nucleophiles and the control of 1,2- versus 1,4-addition to alpha,beta-unsaturated carbonyl compounds
P-Block Chemistry Si, S, P, B

Enolate chemistry (This section will be taught in 2017-18)
Dr MJ Hall

Formation of enolates and pKa
Enolate alkylation; O vs C alkylation, kinetic vs thermodynamic control, 1,3-dicarbonyls and the use of malonates in synthesis
The aldol reaction; aldol, dehydration of products, intramolecular aldol and cross aldol
Acylation of enolates; Claisen and Dieckmann condensations
Tandem processes; Darzens, Baylis Hillman, Robinson etc.
Enamines; formation and reactions

Heteroaromatic Chemistry (This section will be taught from 2018-19 onwards)
Dr MA Carroll

Aromatic systems containing heteroatoms; introduction and overview
Membered heteroatromatics containing one heteroatom; pyrroles, furans and thiophenes
Membered heteroaromatics containing one heteroatom; pyridines
Fused heteroaromatics; indoles and quinolines
Heteroaromatics containing more than one heteroatom

Synthesis
Dr MJ Hall

Classical synthesis and synthetic strategy
Retrosynthetic analysis
Protecting group chemistry
Syntheses of specific molecules drawn from the classical and recent literature and covering molecules of theoretical interest, natural products and pharmaceuticals


Organic Chemistry Laboratory Course
Dr Z McMillan
     
Each student pair does the experiments from the following list:
An investigation into the Stereoselectivity of Wittig Reactions
Synthesis of a Queen Honeybee Pheromone
Discovering Selectivity in the Diels-Alder Reaction

Teaching Rationale And Relationship

In lectures students learn advanced concepts in organic chemistry, encompassing synthetic and mechanistic principles. The small group teaching sessions look over these techniques.

In practical classes competencies in practical procedures, observation, record-keeping and report writing, will be taught and learnt.

Assessment Rationale And Relationship

The examination will test the students’ knowledge and understanding of the content of this module in the context of both synthetic and mechanistic chemistry. Formative assessment in the form of coursework will be set in Semester 1.

The laboratory component practical involves the assessment of a complex selection of skills learnt in about 4 experiments per student, spread over the major areas of inorganic chemistry.