Module FXX-2203:
OC 1 Reactions and Mechanisms

Module Facts

Run by School of Natural Sciences

10 Credits or 5 ECTS Credits

Semester 1

Organiser: Dr Martina Lahmann

Overall aims and purpose

This module comprises different aspects on organic chemistry, and build on the organic functional group chemistry and stereochemistry discussed in modules FXX1101 and FXX1103. Its content will be further explored as part of the tutorial module (FXX 2209).

The first part of the lecture course will focus on anion chemistry. Thus, their formation and chemical properties will be discussed, and a number of synthetically important reactions will be presented. Further retrosynthetic analysis - a problem solving technique for target orientated synthesis - will be introduced and the knowledge on stereochemistry expanded. This is achieved through a mixture of formal lectures, guided self-study material and in class problem-solving. The module will be assessed through a formal exam, and also through on-line assignments linked to the tutorial module (FXX 2209).

Course content

The first part of the module (6 h lectures) will cover the following aspects; carbanion formation and stability, resonance and delocalisation, the nature of electrophiles in organic reactions, α-alkylation (including Knoevenagel type reactions), and activating groups. Within this context, the Aldol reaction, Aldol condensation, Claisen reaction and its variations, crossed Aldol reactions and crossed Claisen reactions, the Michael addition, Robinson annelation, the Wittig reactions (including variations), and the decarboxylation reaction will be discussed. All reactions will be put into the context of their synthetic applications and their reaction mechanisms. The second part of this lecture course (18 lectures and 4 tutorial type activities) will introduce the concept of retrosynthesis, and continue on expanding the knowledge on stereochemistry and synthesis (reactions and mechanisms). The following aspects will be covered: Retrosynthetic analysis - terminology (e.g., retrosynthesis arrow, synthons, various disconnections, FGI, SM, TM, SE) and its application for a variety of organic molecules, advanced functional groups (e.g., hydrazones, oximes), synthetic strategies (protecting group chemistry, selectivity, specificity), introduction and expansion on reactions and their mechanism (including selectivity and stereochemistry), reagent chemistry (e.g. for oxidations, reductions, substitutions, additions), resolution of optical isomers, and chirality without stereogenic centres. New - or earlier only briefly mentioned - reactions(e.g. Diels Alder reaction, Hydroboration, Metathesis) will be introduced, and they will be - as those discussed during the first part of the module - explored in a range of retrosynthetic problems. The material will be taught through formal lectures, tutorial type classes, and self-study material provided on Blackboard, as well by directed reading (textbook and Blackboard).

Assessment Criteria

threshold

Knowledge and understanding of the content covered in the course is basic; Problems of a routine nature are generally adequately solved; Transferable skills are at a basic level.

good

Knowledge base covers all essential aspects of subject matter dealt with in the programme and shows good evidence of enquiry beyond this. Conceptual understanding is good. Problems of a familiar and unfamiliar nature are solved in a logical manner; solutions are generally correct and acceptable. Performance in transferable skills is sound and shows no significant deficiencies.

excellent

Knowledge base is extensive and extends well beyond the work covered in the programme. Conceptual understanding is outstanding. Problems of a familiar and unfamiliar nature are solved with efficiency and accuracy; problem-solving procedures are adjusted to the nature of the problem. Performance in transferable skills is generally very good.

Learning outcomes

  1. Students should be able to demonstrate fundamental knowledge on functional group interconversion and carbon-carbon bond formation, i.e. having developed a fundamental understanding of the underlying mechanistic rationales for reactivity (i.e. being able to draw curly arrow mechanism, perform a formal retro-synthesis on an oligo functional target molecule, recognition of important intermediates), selectivity (i.e. distinguishing and rationalising different types of selectivity) and reagents (i.e. knowledge of standard reagents and their use).

  2. Students should be able to demonstrate the use of Professional Chemistry Language on an Independent User Level (confident and correct use and understanding of basic concepts, mechanisms, terminology and techniques within the course-level).

  3. Students should be able to show problem solving and critical thinking skills by critically analysing, designing and evaluating non-complex synthetic problems within the course-level.

  4. Students should be able to verbalise and apply key concepts and stereochemistry specific terminology to a variety of chemical problems (e.g. assigning absolute configuration including in complex compounds containing multiple stereogenic centres, determining the stereochemical relationship between molecules containing multiple stereogenic centres, fundamental control of stereochemistry and resolution of stereoisomeric mixtures).

  5. Students should be able to demonstrate a fundamental knowledge of specifically anion chemistry, their properties and their chemistry (including the ability to draw curly arrow mechanisms to reactions discussed or similar to reactions discussed during the module).

Assessment Methods

Type Name Description Weight
Examination 80
Blackboard Test 20

Teaching and Learning Strategy

Hours
Lecture 24
Tutorial 4
Private study 72

Transferable skills

  • Literacy - Proficiency in reading and writing through a variety of media
  • Numeracy - Proficiency in using numbers at appropriate levels of accuracy
  • Computer Literacy - Proficiency in using a varied range of computer software
  • Self-Management - Able to work unsupervised in an efficient, punctual and structured manner. To examine the outcomes of tasks and events, and judge levels of quality and importance
  • Exploring - Able to investigate, research and consider alternatives
  • Information retrieval - Able to access different and multiple sources of information
  • Inter-personal - Able to question, actively listen, examine given answers and interact sensitevely with others
  • Critical analysis & Problem Solving - Able to deconstruct and analyse problems or complex situations. To find solutions to problems through analyses and exploration of all possibilities using appropriate methods, rescources and creativity.
  • Presentation - Able to clearly present information and explanations to an audience. Through the written or oral mode of communication accurately and concisely.

Subject specific skills

  • CC5 Skills in the generation, evaluation, interpretation and synthesis of chemical information and data
  • CC8 The ability to adapt and apply methodology to the solution of unfamiliar problems
  • PS3 Problem-solving skills, relating to qualitative and quantitative information
  • PS11 Problem-solving skills including the demonstration of self-direction, initiative and originality
  • PS6 Information technology skills which support the location, management, processing, analysis and presentation of scientific information
  • PS14 Independent learning skills required for continuing professional development
  • SK2 Demonstrate a systematic understanding of fundamental physicochemical principles with the ability to apply that knowledge to the solution of theoretical and practical problems
  • SK3 Gain knowledge of a range of inorganic and organic materials
  • PS16 The ability to work in multi-disciplinary and multi-skilled teams
  • SK4 Demonstrate, with supporting evidence, their understanding of synthesis, including related isolation, purification and characterisation techniques
  • SK6 Develop an awareness of issues within chemistry that overlap with other related subjects
  • SK9 Read and engage with scientific literature
  • SK11. Reading and engaging with scientific literature.
  • CC1 the ability to demonstrate knowledge and understanding of essential facts,concepts,principles and theories relating to theSubject areasCovered in theirProgramme
  • CC2 the ability to applysuch knowledge and understanding to thesolution of qualitative and quantitativeProblems that are mostly of a familiar nature

Resources

Talis Reading list

http://readinglists.bangor.ac.uk/modules/fxx-2203.html

Reading list

Organic chemistry - Clayden, Jonathan, Greeves, Nick, Warren, Stuart G. c2012

And Chemistry3 - most recent edition

Pre- and Co-requisite Modules

Co-requisite of:

Courses including this module