INTERMEDIATE ORGANIC CHEMISTRY - 2018/9

Module code: CHE2024

Module Overview

This is an intermediate level module in organic chemistry, moving from the predominantly functional group approach of Introductory to deal with reactions that build the carbon skeleton. It then moves on to heterocyclic chemistry, which builds upon the standard benzenoid chemistry of Introductory, but applied to more complex systems. The practical part continues to develop skills, but begins to give practice in the reactions taught in the lectures and to encourage a more critical analysis of experiments.

Module provider

Chemistry

Module Leader

CUNNINGHAM ID Dr (Chemistry)

Number of Credits: 15

ECTS Credits: 7.5

Framework: FHEQ Level 5

JACs code: F160

Module cap (Maximum number of students): N/A

Module Availability

Semester 1

Prerequisites / Co-requisites

N/A

Module content

Indicative content includes:


CARBONYL CHEMISTRY: 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, Carbene Chemistry, Preparation of carbocyclic compounds from carbocyclic


           precursors : Reduction of aromatic system, Birch reduction, Ring contractions :

           Favourski reaction, Benzilic acid rearrangement, Ring expansions : BaeyerVilliger reaction, Beckmann rearrangement

 


HETEROCYCLIC CHEMISTRY: Heterocycles: 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; The Beckmann Rearrangement, Crossed Aldol Condensation, The Grignard Reaction, DielsAlder Reaction, Heterocyclic, compound preparation, Epoxidation of 3,5,5-trimethylcyclohex-2-en-1-one

Assessment pattern

Assessment type Unit of assessment Weighting
Coursework COURSEWORK PRACTICAL LABS 30
Examination EXAM 1.5 HOURS 70

Alternative Assessment

No alternative to Examination Failure of practical unit of assessment will be required to attend during the Late Summer Assessment period and complete a defined practical course.

Assessment Strategy

The assessment strategy is designed to provide students with the opportunity to demonstrate:


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 level 4) relevance to synthesis [LOs 1-4, a]
Practicals: Ability carry out typical organic chemistry reactions, and to interpret and analyse them in manner appropriate to the discipline [LOs 1, 3, 4, 5, b, c]


 

Thus, the summative assessment for this module consists of:


Examination: closed book (70%)
Practicals: Six stand-alone practicals (30%)


 

Formative assessment

Formal formative assessment formulates in the form of formal formative tutorials.  Students can opt for informal formative assessment, such as submission of specimen exams, past papers, which will be marked and annotated with informal informative formative comments.

 

Feedback:

During tutorials, but occasionally following enquiries during/after lectures.  Feedback is also provided extensively after practicals, not only on the techniques and procedures, but on the underlying chemistry

Module aims

  • To further develop the organic functional group and mechanistic chemistry introduced in level 4
  • introduce C-C forming reactions and strategies, especially with respect to cyclisations
  • introduce heterocyclic chemistry
  • further develop the skills and practical abilities introduced in HE1 to a level appropriate to pre-independent research

Learning outcomes

Attributes Developed
1 Demonstrate understanding of reactions and mechanisms for carbon-carbon bond formation, including cyclisations K
2 Apply these reactions in strategies for construction of a molecule's carbon skeleton and for modification of heterocycles KC
3 Interpret reaction outcomes in terms of the underlying reactivity and mechanism C
4 Solve basic problems within the context of the reaction types and mechanisms covered C
5 Undertake, and interpret outcomes of, advanced practical organic chemistry T
6 Problem-solving T
7 Manipulative skills T
8 Report writing T

Attributes Developed

C - Cognitive/analytical

K - Subject knowledge

T - Transferable skills

P - Professional/Practical skills

Overall student workload

Independent Study Hours: 85

Lecture Hours: 31

Tutorial Hours: 3

Methods of Teaching / Learning

The learning and teaching strategy is designed to:

facilitate assimilation of a large volume of information by emphasising the 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 (26 hours)

Practical sessions (42 hours)

Formative Tutorials (4 hours)

General explanative, contemplative and summative 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.

Reading list

Reading list for INTERMEDIATE ORGANIC CHEMISTRY : http://aspire.surrey.ac.uk/modules/che2024

Programmes this module appears in

Programme Semester Classification Qualifying conditions
Chemistry 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
Chemistry BSc (Hons) 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
Medicinal Chemistry BSc (Hons) 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 2018/9 academic year.