ORGANIC CARBON-CARBON BOND FORMATION AND HETEROCYCLIC CHEMISTRY - 2020/1

Module code: CHE2044

Module Overview

This module provides a more advanced understanding of Level 4 organic chemistry.

Module provider

Chemistry

Module Leader

ROTH Peter (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

None

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: Favorski reaction, benzilic acid rearrangement, ring expansions: Baeyer–Villiger 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;


  • 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 pattern

Assessment type Unit of assessment Weighting
Coursework Coursework - Laboratory Portfolio 20
Examination Examination (1.5 hr) 80

Alternative Assessment

Alternative assessment: Failure in the laboratory component may require reassessment through a defined practical examination.

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 1-3]

  • 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]



Thus, the summative assessment for this module consists of:


  • Examination: closed book (80%, 1.5 h)

  • Laboratory portfolio: Six stand-alone practicals with 6-7 h in the lab (20%, 42 h plus ca.10 h write-up



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.

Module aims

  • 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.

Learning outcomes

Attributes Developed
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

Attributes Developed

C - Cognitive/analytical

K - Subject knowledge

T - Transferable skills

P - Professional/Practical skills

Overall student workload

Independent Study Hours: 81

Lecture Hours: 25

Tutorial Hours: 2

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 (25 hours)

  • Practical sessions (42 hours)

  • Formative tutorials (2 hours)

  • General self-study (81 hours)


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 ORGANIC CARBON-CARBON BOND FORMATION AND HETEROCYCLIC CHEMISTRY : http://aspire.surrey.ac.uk/modules/che2044

Other information

None

Programmes this module appears in

Programme Semester Classification Qualifying conditions
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 MChem 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 2020/1 academic year.