Retrosynthesis and Aromatics

Learning Outcomes

Knowledge and Understanding

Having successfully completed this module, you will be able to demonstrate knowledge and understanding of:

• Use disconnections to design effective organic synthesis of molecules using a range of known reaction types.
• Explain the structure and bonding of benzene, and the structure and reactivity of heterocycles.
• Apply a range of standard functional group interconversions and functional group additions to enable viable disconnections.
• Design synthetic procedures to make aromatic molecules including heterocycles.

Subject Specific Practical Skills

Having successfully completed this module you will be able to:

• Meet the learning outcomes of a co-requisite practical module.

Retrosynthetic Analysis and the Disconnection Approach: Functional Group Interconversions; Synthesis of amines; Timing of disconnections in synthesis of aromatic compounds; Protecting groups; Functional Group Additions; Ester and ketone alkylation, malonate and acetoacetate chemistry; Decarboxylations; 1,3-, 1,5-, 1,4-, 1,2-disconnections; Alkene formation. Wittig reactions, alkyne reductions (synthetic applications of acetylenes)

Ring formation methods: Dieckmann condensation; Birch reduction of aromatic rings, Robinson annelation; pinacol and acyloin couplings.

Aromaticity and the Chemistry of Aromatic Heterocycles: Structure and bonding in benzene and COT; Introduction to aromatic heterocycles - importance, reactivity, ring-synthesis; Pyrrole, furan, thiophene, pyrazolones, azlactones, indole, benzofuran, imidazole, oxazole, thiazole, pyridine, pyridinium, quinoline, isoquinoline.

Lectures, small group tutorials and laboratory sessions.

Summative

This is how we’ll formally assess what you have learned in this module.