ORGANIC CARBON-CARBON BOND FORMATION AND HETEROCYCLIC CHEMISTRY - 2023/4
Module code: CHE2044
This module builds upon the basic concepts taught at FHEQ level 4 and prepares students for the advanced research-led concepts of FHEQ level 6 and, where applicable, for relevant placements. Specifically, new reactions leading to carbon–carbon bond formation are explained, while the concepts of aromatic chemistry are expanded to heteroaromatics.
Chemistry and Chemical Engineering
ROTH Peter (Chst Chm Eng)
Number of Credits: 15
ECTS Credits: 7.5
Framework: FHEQ Level 5
JACs code: F160
Module cap (Maximum number of students): N/A
Overall student workload
Independent Learning Hours: 51
Lecture Hours: 22
Tutorial Hours: 3
Practical/Performance Hours: 42
Guided Learning: 10
Captured Content: 22
Prerequisites / Co-requisites
Indicative content includes:
- Aldol & Claisen condensations, the Wittig reaction, malonic and acetoacetic ester syntheses, Michael addition, examples of syntheses using carbonyl chemistry
Preparation of carbocyclics:
- Cyclisation by intramolecular nucleophilic addition, general considerations, diketone synthesis, Dieckmann cyclisation, Thorpe-Ziegler reaction, Michael reaction, reductive cyclisation, acyloin condensation, pinacol reactions, acid catalysed cyclisation, dienes, cyclisations using enamines, Stork reaction
- Diels–Alder reactions and introduction to frontier molecular orbital theory, some examples of syntheses using Diels–Alder reactions, electrocyclic reactions, thermal/photochemical reactions (disrotatory, conrotatory), further FMO theory
- Preparation of carbocyclic compounds from carbocyclic precursors: reduction of aromatic system, Birch reduction, ring contractions: Favorski reaction, benzilic acid rearrangement, ring expansions: Baeyer–Villiger reaction, Beckmann rearrangement
- relevant examples, nomenclature
- The chemistry of pyridine: synthesis, structure and properties, general reactivity of pyridines,
- quinoline and isoquinoline: synthesis, structure and properties, general reactivity of quinolines and isoquinolines
- pyrrole, furan and thiophene: synthesis, structure and properties, general reactivity of pyrroles, general reactivity of furans and thiophenes, problem solving sessions
Practical organic chemistry
- Crossed aldol condensation
- The Beckmann rearrangement
- The Grignard reaction
- Diels–Alder reaction
- Heterocyclic, compound preparation
- Epoxidation of 3,5,5-trimethylcyclohex-2-en-1-one
|Assessment type||Unit of assessment||Weighting|
|Practical based assessment||Laboratory Exercise 1||4|
|Practical based assessment||Laboratory Exercise 2||4|
|Practical based assessment||Laboratory Exercise 3||4|
|Practical based assessment||Laboratory Exercise 4||4|
|Practical based assessment||Laboratory Exercise 5||4|
|Practical based assessment||Laboratory Exercise 6||10|
|Examination||2HR CLOSED BOOK EXAMINATION||70|
For the laboratory exercises an alternative written assessment can be set. This is based on analysing or explaining experimental data, or detailing experimental techniques.
Thus the summative assessments consists of;
- Practicals: Ability to carry out typical organic chemistry reactions, and to interpret and analyse them in a manner appropriate to the discipline [LOs 1, 2, 4]
- Examination: Application of knowledge to important and archetypal organic chemistry explanations; extension of knowledge to a wider range of organic chemistry examples, with increased (relative to FHEQ level 4) relevance to synthesis [LOs 1–3]
Thus, the assessment for this module consists of:
- Examination (2 h): closed book
- Laboratory portfolio: Six stand-alone practicals
- Formative assessment: The tutorials will be formative; comprising material designed to guide the student and give practice in the application of the lecture material to extended and unseen problems
- Feedback: Formal feedback is provided on tutorial work, optionally on past exam papers and explicitly provided on all aspects of the practical work.
- Build upon the basic organic chemistry in Level 4;
- Introduce more complex reactions and new mechanisms and concepts;
- Provide further training in, and practice of, common laboratory procedures on reactions covered in the lectures.
|001||Routinely apply basic concepts of structure, bonding and reactivity to the more complex reactions introduced in this module||KC|
|002||Demonstrate an understanding, e.g. by interpreting outcomes, of more advanced concepts (in particular C-C bond-forming reactions, and heterocyclic chemistry)||KC|
|003||Demonstrate an ability to apply these concepts to novel situations not explicitly covered in the lectures, e.g. by designing reactions for a specific outcome||C|
|004||Apply common laboratory techniques to prepare and analyse organic compounds of the type covered in the lectures and to report upon the work in the correct style||KCPT|
C - Cognitive/analytical
K - Subject knowledge
T - Transferable skills
P - Professional/Practical skills
Methods of Teaching / Learning
The learning and teaching strategy is designed to facilitate assimilation of a large volume of information by emphasising the underlying mechanistic approach. The same approach is designed to allow application to unseen and more advanced cases. The practicals develop skill in more advanced techniques as well as reinforcing basic, but ubiquitous, ones. They also allow students to appreciate the relevance of the lecture material to the real-world chemistry environment.
The learning and teaching methods include:
- Formal lectures: average of 2 hours a week for 11 weeks
- Practical sessions: 6 sessions
- Formative tutorials: 3 sessions
- General self-study
Indicated Lecture Hours (which may also include seminars, tutorials, workshops and other contact time) are approximate and may include in-class tests where one or more of these are an assessment on the module. In-class tests are scheduled/organised separately to taught content and will be published on to student personal timetables, where they apply to taken modules, as soon as they are finalised by central administration. This will usually be after the initial publication of the teaching timetable for the relevant semester.
Upon accessing the reading list, please search for the module using the module code: CHE2044
Laboratory work forms a significant part of this module, aligning with Royal Society of Chemistry (RSC) accreditation of the degree programmes. Labs will be carried out individually or in pairs thus enhancing students’ awareness of Health & Safety practices and Standard Operating Procedure (SOP) of instruments in the lab; these relate both to Employability skills for graduate chemists and their Resourcefulness & Resilience.
Within the University’s broader education strategy, this module particularly develops students’ Digital Capabilities. Students will use instruments and software to plot and interpret data from samples prepared in the laboratory sessions.
Sustainability is included in this module in the context of green and atom-economical synthesis.
Programmes this module appears in
|Chemistry MChem||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
|Chemistry with Forensic Investigation BSc (Hons)||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
|Chemistry BSc (Hons)||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
|Medicinal Chemistry BSc (Hons)||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
|Chemistry with Forensic Investigation MChem||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
|Medicinal Chemistry MChem||1||Compulsory||A weighted aggregate mark of 40% is required to pass the module|
Please note that the information detailed within this record is accurate at the time of publishing and may be subject to change. This record contains information for the most up to date version of the programme / module for the 2023/4 academic year.