Module and Programme Catalogue

Search site

Find information on

2019/20 Undergraduate Module Catalogue

CHEM3231 Reactivity in Organic Chemistry - Principles and Applications

10 creditsClass Size: 100

Module manager: Professor Chris Rayner
Email: c.m.rayner@leeds.ac.uk

Taught: Semester 2 View Timetable

Year running 2019/20

Pre-requisite qualifications

Level 2 in Chemistry or Level 2 in Joint Honours (Science) with Chemistry or equivalent.

Pre-requisites

CHEM2141Introduction to Organic Synthesis
CHEM2241Organic Structure and Mechanism

Module replaces

CHEM3230 Reaction Intermediates and Physical Organic Chemistry

This module is not approved as a discovery module

Objectives

The object of this course is to provide students with an understanding of reactivity in organic chemistry, and how this relates to applications in the real world. Using fundamental concepts of organic chemistry, such as reactive intermediates, the factors influencing their reactivity and areas where control of reactivity are important, the module will put these principles into context using real world examples which students can relate to. The module will include areas such as the nature of reactive intermediates, catalysis (including biological catalysis), solvents, hazardous materials, scale-up of chemical reactions, and sustainability.

Learning outcomes
On completion of this module, students should:
(1) Have a broad appreciation of the nature of reactive intermediates, and factors affecting their stability and reactivity.
(2) Have an understanding of the importance of carbenium ions in chemical processes and their applications.
(3) Understand the reactivity of carbenes, nitrenes and radicals, and their applications.
(4) Understand the factors affecting reaction kinetics, including reaction order, solvent effects, catalysis (including biological catalysis) and structural features controlling reactivity.
(5) Understand the challenges associated with scale-up of a chemical process, and alternative approaches.
(6) Understand the concepts of sustainability, life cycle assessment and renewable materials.


Syllabus

REACTIVE INTERMEDIATES
Carbenium ions and carbanions.
Carbenes, radicals.
Comparison of electronic structures, stabilising/destabilising effects.
Carbenium ions.
Exploitation of reactivity effects in protecting group chemistry, with examples.

SPECIFIC ACID AND BASE CATALYSIS; GENERAL ACID AND BASE CATALYSIS
Effect of substitution on reactivity.
Reversibility of formation, kinetic vs. thermodynamic control.
Neighbouring group participation.
Ritter reaction, and synthesis of Crixivan.
Cationic cascade leading to taxol synthesis (or maybe steroid). Opportunity for some anticancer or steroids background.
Biological catalysis and kinetic isotope effects.
Nucleophilic catalysis – chemical and biochemical catalysis of acylation.

CARBENES AND CARBENOIDS
Generation, properties and reactions.
Synthesis of pyrethrin decamethrin; other important agrochemicals.
Wolff rearrangement, synthesis of the sex pheromone, Grandisol.
C-H insertion as trapping agent in biological systems for determining location of binding (diazirines).

NITRENES
Curtius rearrangement. Formation and reactions of isocyanates; Methylisocyanate (Bhopal); use of isocyanates for making beta-lactams and polyurethanes.

REACTION KINETICS INCLUDING PRINCIPLES OF CHEMICAL ANALYSIS
Solvents and solvent effects.
Ionic reactions, solubility (including of gases), Finkelstein, concentration effects. E.g. macrocylisations, neat reactions, biphasic reactions and phase transfer catalysis.

RADICALS
Radical generation.
Rate effects (radical clocks), inter vs intramolecular processes.
Radicals in synthesis.
Antioxidants. Preservatives. Vitamins E and C as radical traps and as biological protecting agents.

REACTIONS INVOLVING WEAK HETEROATOM-HETEROATOM BONDS
Toray process to make oxime. Epoxidation and Baeyer Villiger reactions.
Other reagents with weak bonds, e.g. peroxides (H2O2, TBHP, hydrazine). Rocket propellants vs Oxidative hair dyeing using H2O2.
When reaction kinetics get out of hand...
Hazardous reagents and reactions.
From explosives to heart stimulants. Glycerol trinitrate/nitroglycerine and related chemistry.

BATCH VS. CONTINUOUS REACTIONS
Implications for large scale/process chemistry.
Principles of continuous reactors.
Use with hazardous reagents (hydrogenation, ozonolysis).
Microwaves in pharmaceutical discovery – thermal rate enhancements and selectivity changes.
Introduction to Green Chemistry and Sustainability.
Principles of reaction efficiency.
Renewable materials and life cycle analysis.
Chemistry in 50 years time.

Teaching methods

Delivery typeNumberLength hoursStudent hours
Workshop21.002.00
Lecture181.0018.00
Private study hours80.00
Total Contact hours20.00
Total hours (100hr per 10 credits)100.00

Private study

20 hours = workshop preparation and assignments
20 hours = reading of literature and course text books
20 hours = digestion of notes
20 hours = examination preparation

Opportunities for Formative Feedback

Students will be monitored through submission and quality of assessed workshop work and attendance at lectures and non-assessed workshop.
Students will also be informally monitored through discussions in classes.

Methods of assessment


Coursework
Assessment typeNotes% of formal assessment
AssignmentAssessed Workshop12.00
Total percentage (Assessment Coursework)12.00

Only one of the two workshops will be assessed. Assessed workshop will be submitted before Easter, with feedback on return.


Exams
Exam typeExam duration% of formal assessment
Standard exam (closed essays, MCQs etc)2 hr 00 mins88.00
Total percentage (Assessment Exams)88.00

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

Reading list

There is no reading list for this module

Last updated: 02/11/2018

Disclaimer

Browse Other Catalogues

Errors, omissions, failed links etc should be notified to the Catalogue Team.PROD

© Copyright Leeds 2019