ORGANIC SYNTHESIS AND SPECTROSCOPY - 2023/4

Module Overview

This module builds on fundamental concepts introduced to students in Level 4 (CHE1041 Organic Structure, Reactivity and Functional Groups) and Level 5 (CHE 2044 Organic carbon-carbon bond formation and Heterocyclic Chemistry) organic chemistry courses and Level 5 Spectroscopy module (CHE2036 Applied Organic Spectroscopy).  

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 and Chemical Engineering

Module Leader

MULHOLLAND Dulcie (Chst Chm Eng)

Number of Credits: 15

ECTS Credits: 7.5

Framework: FHEQ Level 6

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 1,5- dicarbonyl compounds¿ alpha, beta-unsaturated and 1,3-dihydroxy 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: Baylis Hillman 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

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 

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

Thus, the summative assessment for this module consists of:

• In-class test/assessed workshop on spectroscopy: (20%,  4 hour, On-line) 

• Examination (80%, 4 hour, On-line) 

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. 

Module aims

• To 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
• To provide students with the skills to identify organic compounds by spectroscopy

Learning outcomes

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

• Spectroscopy workshop (Contact = 4 x 2 h over 8 weeks, plus on-line test)

• 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

https://readinglists.surrey.ac.uk
Upon accessing the reading list, please search for the module using the module code: CHE3061

Other information

 Each student will gain an awareness of Sustainability concepts through discussions on toxicity and environmental responsibility in organic synthesis (green synthesis) and atom efficient synthesis. The spectroscopy content contributes to student awareness of Digital Capabilities through material on the different pulse sequences used to obtain different types of spectra. 

The chemical industry is global, affected by supply of raw materials and world prices, hence the course encompasses an understanding of Global and Cultural Capabilities and introduces the concepts of Resourcefulness and Resilience. Resourceful and Resilience is developed through problem solving requirements of the course. 

Programmes this module appears in

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 2023/4 academic year.