2020/21 Taught Postgraduate Module Catalogue

CHEM5195M Synthesis and Characterisation of Organic Molecules

15 creditsClass Size: 20

Module manager: Dr Stuart Warriner
Email: S.L.Warriner@leeds.ac.uk

Taught: 1 Jan to 31 May View Timetable

Year running 2020/21

Pre-requisite qualifications

Degree in Chemistry, Chemical engineering or related discipline

Module replaces

CHEM5126 Organic Synthesis for Fine Chemical and Pharmaceutical Synthesis

This module is not approved as an Elective

Module summary

This module will increase students’ proficiency in 1) understanding and designing chemical reactions in advanced synthetic organic chemistry, and 2) understanding the structural analytical techniques of mass spectrometry and nuclear magnetic resonance spectroscopy and using analytical data to elucidate molecular structure.

Objectives

Be able to understand and apply more advanced concepts in selective organic synthesis and its application in industrially related areas. Specifically the module will enable students to:

- be familiar with common protecting groups and methods for slective protection
- be familiar with important methods for the selective creation of carbon-carbon bonds using enolate equivalents and how relative stereochemistry is controlled in aldol reactions.
- be familiar with approaches to create 1,2, and 1,4 dioxygenation patterns and appreciate their importance to retrosynthetic analysis
- understand the importance of heterocyclic compounds and be capable of devising methods for synthesis of a variety of heterocycles by either ring synthesis or substitution reactions;

Understand key organometallic, particularly organo palladium based methods in synthesis

- be able to use a combination of 1D, 2D NMR, IR spectroscopy and mass spectrometry to determine the structures of complex organic molecules.

Learning outcomes
Students will be able to explain and apply the principles of:

- Understanding of the principles which control the selective reaction of enolates and their equivalents and organometallic reagents.
- Capability to explain, from a mechanistic basis, the selectivity of reactions using the principles described.
- The ability to plan and propose synthetic routes to unseen target molecules using the chemistry discussed.
- Understanding of the structure and bonding within heterocycles and how this controls heterocyclic properties.
- Understanding of industrially important Pd catalysed coupling reactions and their mechanistic basis
- Knowledge of a variety of strategies for the synthesis and functionalization of different heterocyclic classes and the ability to propose syntheses of unseen examples.
- The capability to explain the variety of heterocyclic chemistry at a mechanistic level.
The capability to interpret NMR spectra and report data in a manner required in the chemical literature
The capability to use analytical data to determine the structure of unknown compounds.

Syllabus

- Preparation and use of stable enolate equivalents, including silyl enol ethers.

- Important organometallic reagents in synthesis including palladium-catalysed cross coupling reactions and organolithium reagents.

- Development of efficient synthetic strategies: approaches to the synthesis of 1,3/1,5 and 1,2/1,4 difunctionalised molecules respectively,

-use of protecting groups in synthesis.

- Properties of heterocycles, acid and basic properties.

- Synthesis of aromatic and non-aromatic heterocycles.

- Substitution reactions of pyridines, including methods used to activate pyridines to electrophilic attack.

- synthesis, reactions, and applications of 5-membered ring aromatic heterocycles inclusing pyrroles, furans and thiophenes.

- Synthesis and functionalization of indoles.

Applications of NMR: Revision of level 1: chemical shift tables and basic multiplets; second order effects; advanced multiplet analysis, the Karplus equation; Other nuclei: 13C, DEPT etc; Other nuclei: inorganic examples; 2D NMR; Advanced NMR techniques: NOE and NOeSY

Mass spectrometry: Techniques; accurate mass and isotope patterns; Advanced MS

Teaching methods

Delivery type	Number	Length hours	Student hours
Lecture	28	1.00	28.00
Tutorial	3	1.00	3.00
Private study hours			119.00
Total Contact hours			31.00
Total hours (100hr per 10 credits)			150.00

Private study

Pre-reading will be expected before lectures. Post-lecture students are expected to review their notes and work independently on problems – 101 h

Further problems will be set for students to prepare for tutorials – 6 h

Completing structure determination assessment – 12 h

Opportunities for Formative Feedback

Formative exercises for workshops, and regularly-spaced online quizzes

Methods of assessment

Coursework

Assessment type	Notes	% of formal assessment
Assignment	Mid-term coursework	10.00
Written Work	Data analysis of NMR spectral data	20.00
Total percentage (Assessment Coursework)		30.00

Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated

Exams

Exam type	Exam duration	% of formal assessment
Online Time-Limited assessment	48 hr 00 mins	70.00
Total percentage (Assessment Exams)		70.00

Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated

Reading list

The reading list is available from the Library website

Last updated: 07/08/2020 18:22:57

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