ORGANIC SYNTHESIS AND SPECTROSCOPY - 2020/1

Module code: CHE3061

Module Overview

This is a high level module in organic chemistry, moving from the predominantly functional group approach of Level 4 beyond the skeletal construction approach of Level 5, to deal with modern and more conceptually challenging reactions and strategies for dealing with multistep syntheses. These are the reactions that are commonly used in contemporary organic synthetic chemistry.

Module provider

Chemistry

Module Leader

CUNNINGHAM Ian (Chemistry)

Number of Credits: 15

ECTS Credits: 7.5

Framework: FHEQ Level 6

JACs code:

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

Module Availability

Semester 1

Prerequisites / Co-requisites

None

Module content

Indicative content includes:

Revision of organic reactions: Revision of mechanisms

Retrosynthetic Analysis: Terms, definitions and basic concepts; retrosynthetic analysis: aromatic compounds; retrosynthetic Analysis: alcohols and carbonyl compounds; retrosynthetic analysis: 1,2, 1,3, 1,4 and 1,5dicarbonyl compounds; -unsaturated and 1,3dihydroxy compounds; retrosynthetic analysis: carbocyclic and heterocyclic; compounds

Modern reactions: Polar reactions in synthesis, radical reactions in synthesis, pericyclic reactions in synthesis, asymmetric synthesis – an introduction

Catalytic reactions in organic chemistry: Concept of catalysis. Mechanistic implications: creating a catalytic cycle. Reactions using metal catalysis; palladium-catalysed cross-coupling reactions: Heck, Sonogashira, Stille and Suzuki reactions; Pauson-Khand reaction. Small organic molecules as catalysts: BaylisHillman reaction; olefin metathesis

Multicomponent reactions: Solid-phase synthesis and combinatorial chemistry

Spectroscopy: Workshop 1: Introductory revision problems using 1D NMR (1H, 13C), MS, IR, UV. Use of the coupling constant, Karplus equation, coupling in aromatic systems and long range coupling; Workshop 2: Use of COSY, HSQC, DEPT, HMBC and NOESY spectra in structure determination with worked examples; Workshops 3 & 4: Structural determination of compounds using natural products and synthetic compounds (terpenoids; oxygen heterocyclics (chalcones, flavonoids); alkaloids) as examples

Assessment pattern

Assessment type Unit of assessment Weighting
Examination Examination (1.5 hours) 70
Coursework Coursework 15
School-timetabled exam/test Spectroscopy in-class test 15

Alternative Assessment

N/A

Assessment Strategy

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

• Examination and coursework: Assimilation of knowledge and its application to problems in modern organic chemistry [LOs 1-6]

• In-class test/assessed workshop on spectroscopy: Ability to assign structure based on spectra [LOs 4]

Thus, the summative assessment for this module consists of:

• Coursework: Problem solving on aspects of the course (15%, 18 h over 8 weeks) [LOs assessed 1-3, 5]

• In-class test/assessed workshop on spectroscopy: (15%, 2 h ICT) [LOs 4]

• Examination: 1.5 hours, closed book (70%) [LOs assessed 1-5]

Formative assessment

Formal formative assessment is mainly in the spectroscopy workshops. There is also formative assessment in example problems posted to SurreyLearn for students to attempt and receive written or verbal feedback; also students can opt for informal formative assessment (submission of specimen exams, past papers, etc.) which will be marked and annotated. Feedback: Feedback is provided optionally on the formative practice problems. Coursework is marked and returned with feedback in time for the revision period.

Module aims

  • provide students with the appropriate advanced material in organic chemistry to allow them to describe and methodically rationalize a representative range of standard modern reactions/syntheses
  • provide students with the skills to identify organic compounds by spectroscopy

Learning outcomes

Attributes Developed
001 Demonstrate a conceptual understanding of modern advanced organic reactions (including their scope), including abstract concepts (combinatorial) K
002 Explain chemo‐, regio‐ and stereo‐selectivity where observed in given reactions CK
003 Analyse a chemical structure in terms of the retrosynthetic approach to its multistep synthesis CK
004 Solve problems of structure using a range of spectroscopic techniques, particularly NMR (K, C, P – spectroscopy and practical work tend to be intertwined in organic chemistry) CKP
005 Show critical evaluation of different approaches to specific problems in synthesis C
006 Reviewing, assess and demonstrate critical thinking T

Attributes Developed

C - Cognitive/analytical

K - Subject knowledge

T - Transferable skills

P - Professional/Practical skills

Overall student workload

Workshop Hours: 10

Independent Study Hours: 118

Lecture Hours: 22

Methods of Teaching / Learning

The learning and teaching strategy is designed to:

give the student a good high level knowledge base, but also but the analytical and problem-solving skills to solve unseen (but related), and to attempt some new concepts; all within the context of current practice in organic synthesis.

The learning and teaching methods include:

• Lectures 20, plus two revision lectures = 22 L

• Problem-solving coursework based on the lectures (18 h over 8 weeks)

• Spectroscopy workshop (Contact = 4 x 2 h over 8 weeks, plus self-study time ca. 18 h, plus In-class test assessed workshop 2 h)

• General student independent 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 ORGANIC SYNTHESIS AND SPECTROSCOPY : http://aspire.surrey.ac.uk/modules/che3061

Other information

None.

Programmes this module appears in

Programme Semester Classification Qualifying conditions
Chemistry with Forensic Investigation BSc (Hons) 1 Optional 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

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.