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This document only provides information for the academic year selected and does not form part of the student contract
School:
School of Applied Sciences
Credit Rating:
20
Level (including FHEQ):
M (FHEQ Level 7)
Graded or Non Graded:
Graded
Version Valid From:
2023-09-12
Module Leader:
Karl Hemming
Version Number
2024.01
Learning Methods
Lecture
Guided Independent Study
Requirements
Recommended Prior Study
Pre-requisites
Professional Body Requirements
Royal Society of Chemistry
Synopsis
This module draws together the basic concepts of synthesis and reaction mechanisms in the context of providing methods for designing suitable synthetic routes to target compounds and also extends the range of reaction types to include pericyclic reactions.
The module introduces contemporary preparative methods for the synthesis of organic compounds. … For more content click the Read More button below.
The reaction mechanism component draws together concepts in both physical and mechanistic organic chemistry; this section of the course covers those techniques that can be used to differentiate between mechanistic types. The use of product analysis, activation parameters, linear free energy relationships and isotope effects to determine reaction mechanisms are included.
Learning Strategy
Lectures will be used to deliver the majority of the material. Tutorials will be used to develop the problem solving ability of the students.
Outline Syllabus
Kinetics and transition state theory; bond making and breaking, rate laws and mechanism, determination of transition state structures, isotope effects, linear free energy relationships, thermodynamic activation parameters, selected examples of mechanisms (acyl transfer, substitutions and eliminations). Pericyclic reaction types including cycloadditions, sigmatropic rearrangements, electrocyclic reactions and group transfers. The formation … For more content click the Read More button below.
Synthetic methods for the synthesis of organic compounds. Contemporary methods of synthesis. Synthetic strategy and choice of route. Retrosynthetic analysis (the disconnection approach) – further aspects.Selectivity in synthesis illustrated by selective enolate formation; Cram and Felkin-Ahn models; allyl borane chemistry, aldol reactions.
Asymmetric synthesis, including Zimmerman-Traxler models for enantioselectivity using Evans' auxiliary for alkylations and aldols, Sharpless dihydroxylation, aminohydroxylation, models for enantioselectivity for CBS reduction, asymmetric Diels-Alder reactions.
Swern oxidation; oxidation using TPAP and Dess-Martin periodinane.
Sulfur ylides and their reactions.
1,3-dipolar cycloadditions.
2+2+2 and other cycloadditions.
Organocatalysis – introduction, examples and outlook.
Multi-component reactions. Combinatorial chemistry.
Learning Outcomes
On successful completion of this module students will
1.
be able to have a systematic knowledge of the techniques of physical organic chemistry and their application in a research environment.
2.
be able to have a knowledge and an understanding of contemporary methods used in the synthesis of known and novel organic compounds including the use of pericyclic reactions and reactions involving radicals and carbenes as intermediates.
3.
be able to have a knowledge of the principles involved in applying retrosynthetic analysis and its application in the design of synthetic routes that are regio-, chemo-, stereo- and enantioselective.
4.
be able to design highly selective routes to novel organic compounds using retrosynthetic analysis;.
5.
able to design synthetic routes using contemporary methods.
6.
be able to devise experiments to test hypotheses of reaction mechanisms and be able to propose solutions to mechanistic problems generated within a research environment.
Formative Assessment
Assessment 1: Other
Summative Assessment
Assessment 1: In-Class Test
Assessment 2: Exam
Assessment 3: Practical Skills Assessment
Assessment Criteria
Students should demonstrate knowledge of the theoretical aspects of organic reaction mechanisms in coursework. They should show an ability to apply knowledge to the design of synthetic routes and to determining mechanisms of reactions in the final exam. The final exam will have a significant problem solving component.