PH2S109 - Synthetic Organic and Heterocyclic Chemistry 01 Aug 2023 - 31 Jul 2029 | Version 1

Associated Module Information

Module Code: PH2S109
Module Title: Synthetic Organic and Heterocyclic Chemistry
Faculty: Faculty of Computing, Engineering and Science
Faculty Group: Applied Sciences
Faculty Sub Group: Chemistry and Pharmaceutical Science
Module Leader: Rehana Karim
Module Team: Rehana Karim
First Intended Intake: SEP 2028 Final Year of Intake: 2028
Date Closed:
Credit Value: 20 Credit Level: 5
Language: English
Percentage of Module Taught in Welsh: 0
Equivalent Module:
HECOS codes: 100422 - organic chemistry 100423 - pharmaceutical chemistry
HECOS Code Weighting: 90 10

Document Version Information

Version 1
Valid From 01 Aug 2023
Valid To 31 Jul 2029

Module Aims

  1. To extend the students' knowledge of synthetic transformations and to provide the student with an appreciation of the strategy in organic synthesis.
  2. To enable students to use retrosynthetic analysis and suitable synthetic strategies for the research and development of drugs and compounds of commercial value.
  3. To provide a comprehensive introduction to aromatic heterocycles and also enable students to understand the related reactivity, synthesis and applications.

Content Summary

The Chemistry of Carbonyl Compounds:

Review of structure, bonding and nomenclature of the carbonyl functionality containing compounds (aldehydes/ketones/carboxylic acids/acid chlorides, anhydrides/esters/amide and nitriles). Overview of organic reactions involving carbonyl compounds and various reagents such as Grignard, Gillman reagents and a variety of reducing and oxidizing agents.

Overview of acyl substitution (NAS), nucleophilic addition reactions of carbonyl compounds, acetals formation reactions of aldehydes/ketones and their use as protecting groups, ylides formation and the Wittig reaction.

The carboxylic acids and their derivatives: reactivity, synthesis and preparation of derivatives via Fischer esterification reaction etc.

Rationalisation of the approaches adopted in planning the synthesis of organic compounds. Introduction to some interesting carbon-carbon bond forming reactions and functional group interconversions. The devising of plans/strategies for the synthesis of small organic molecules, drugs and compounds of commercial interest through retrosynthetic analysis of a target.

Introduction to Heterocyclic Chemistry:

Introduction - General nature of heterocyclic compounds and aromatic heterocycles. Heterocyclic structures in natural compounds. Recap of benzene - structure and reactivity.

Review of aldol, Michael addition, imine and enamine formation reactions.

Reactivity of p -excessive heteroaromatics - Electronic structure and effect on reactivity. Electrophilic (and nucleophilic) substitution reactions of a range of heterocyclic compounds such as pyrroles, indoles, furans, thiophenes, and azoles. Reactivity of selected functionalised derivatives.

Reactivity of p -deficient heteroaromatics - Electronic structure and effect on reactivity. Electrophilic and nucleophilic substitution reactions of selected heterocyclic compounds. Reactions of pyridines, and their benzo- fused analogues. Reactions at the heteroatoms of aromatic heterocyclic structures of interest. Reactivity of N-oxides and some functionalised derivatives.

Learning and Teaching Methods

Activity Type Hours
Lecture 18
Seminar 18
Practical classes and workshops 12
Independent Study 70
Directed Study 82
Total Hours Selected 200

Learning Outcomes

# Learning Outcome
LO1 Rationalise the outcomes of a variety of organic reactions and utilise the knowledge of synthetic strategies/reagents to plan/design a good organic synthesis.
LO2 Critically evaluate strategies for the synthesis of a wide range of aromatic heterocyclic compounds and utilise technical and theoretical skills to carry out research/laboratory work safely.

Module Requisites

Code Title Requisite Type
MOD013087 Organic Molecules: their Structure, Reactivity and Analysis pre-requisite
}

Assessment Criteria

Assessment Category Assessment Type Description Duration Word Count Weight (%) Best of? Pass Mark
Synchronous Onsite Practical Assessment Practical Coursework (Onsite) 1 Exercises undertaken in class or in laboratory aimed at assessing the application of knowledge, analytical, problem-solving or evaluative skills. 0 N/A 50 No 40
Asynchronous Assessment Report 1 Written assignment on a range of topics such as organic synthesis, heterocyclic chemistry and retrosynthetic analysis. 0 2000 50 No 40

Assessment Matrix

Assessment Type Learning Outcomes
LO1 LO2
Practical Coursework (Onsite) 1
Report 1

Reading List

Davies, D.T. (1992) Aromatic heterocyclic chemistry. Oxford Chemistry Primers: Oxford University Press.

Gilchrist, T. L. (1997) Heterocyclic chemistry. 3rd ed. Harlow: Longman.

Joule, J.A. and Mills, K. (2010) Heterocyclic chemistry. 5th ed. Chichester: Wiley.

Patrick, Graham L. (2013) An introduction to medicinal chemistry. 5th ed. Oxford: Oxford University Press.

Silverman, R.B. and Holladay, M.W. (2014) The organic chemistry