INTERMEDIATE ORGANIC CHEMISTRY - 2017/8

Module code: CHE2024

Module provider

Chemistry

Module Leader

CUNNINGHAM ID Dr (Chemistry)

Number of Credits

15

ECT Credits

15

Framework

FHEQ Level 5

JACs code

F160

Module cap (Maximum number of students)

N/A

Module Availability

Semester 1

Overall student workload

Independent Study Hours: 85

Lecture Hours: 31

Tutorial Hours: 3

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.

Prerequisites / Co-requisites

N/A

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 aims

To further develop the organic functional group and mechanistic chemistry introduced in level 4

To further develop the organic functional group and mechanistic chemistry introduced in level 4

To introduce heterocyclic chemistry

To further develop the skills and practical abilities introduced in HE1 to a level appropriate to independent research

Learning outcomes

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

Attributes Developed

C - Cognitive/analytical

K - Subject knowledge

T - Transferable skills

P - Professional/Practical skills

Module content

  




 

CARBONYL CHEMISTRY




1-3


Aldol,& Claisen condensations, the Wittig reaction.




Malonic and Acetoacetic Ester syntheses, Michael addition




Examples of syntheses using carbonyl chemistry



 

PREPARATION OF CarbocyclicS




4-14


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: Favorski reaction, Benzilic acid rearrangement




Ring expansions: Baeyer-Villiger reaction, Beckmann rearrangement



 

HETEROCYCLIC CHEMISTRY




15-25


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




38 hours


The Beckmann Rearrangement

Crossed Aldol Condensation

The Grignard Reaction

Diels-Alder Reaction

Heterocyclic compound preparation

Epoxidation of 3,5,5-trimethylcyclohex-2-en-1-one





 

 

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 (25 hours)

Practical sessions (38 hours)

Tutorials (2 hours)

 

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

Reading list

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

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 2017/8 academic year.