CH2OR1-Further Organic Chemistry

Module Provider: Chemistry
Number of credits: 20 [10 ECTS credits]
Level:5
Terms in which taught: Autumn / Spring / Summer module
Pre-requisites:
Non-modular pre-requisites:
Co-requisites:
Modules excluded:
Current from: 2022/3

Module Convenor: Dr John McKendrick
Email: j.e.mckendrick@reading.ac.uk

Type of module:

Summary module description:

Learn the chemistry necessary to make some of the most important molecules that you encounter every day, be they medicines, household products or cosmetics. The ability to manipulate and make new C-C bonds opens up a world of interdisciplinary science. This module covers many of the ways organic chemists make molecules whose structure is limited only by our imagination.

Aims:

To build on the basic concepts of organic chemistry with a more detailed treatment of selected topics.

Assessable learning outcomes:

Students who have successfully completed this module will:

• Have an appreciation for the utility of the carbonyl group in Organic Chemistry.


• Appreciate how structure, shape and reactivity are linked when considering Organic reactions.


• Explain how Organic chemists have studied and unravelled the mechanism of Organic reactions.

Additional outcomes:
The tutorial/workshop environment will improve the studentsô€€’ oral and presentation skills.

Outline content:

Further Carbonyl Chemistry: Revision of alpha-acidity of carbonyl compounds. The aldol condensation reaction, crossed aldol condensations, Claisen condensation, Dieckmann condensation, the use of 1,3-dicarbonyl compounds, decarboxylation of 1,3-keto-acids, Michael addition reactions, Robinson annulation. (6 lectures)

Organometallics: Methods for forming C-C bonds using organometallic reagents; basic aspects of preparative carbanion chemistry. (5 lectures)

Radical Reactions in Synthesis: The properties and use of free radicals in synthesis will be discussed. Areas covered will include radical addition reactions, radical cyclisations. Tandem radical reactions, the acyloin reaction and the Birch reduction. (5 lectures)

Molecular Rearrangements: Topics covered will include the Beckmann, pinacol, Curtius, Hofmann, Baeyer-Villiger and Lossen rearrangements and their use for the synthesis of molecules of industrial importance. (5lectures)

Conformational Analysis: Differences between conformational and configurational isomers; staggered and eclipsed forms of ethane; butane and butane derivatives; elimination reactions; cyclic systems; small, normal, medium and large rings; entropy and enthalpy factors in ring formations; conformational isomerisation in cyclohexane and relationship to reactivity; decalin systems and steroids. Synthesis of Alicyclic Compounds: The methods available for the synthesis ofsmall, medium and large carbo- and hetero-cyclic rings will be outlined, with suitable examples. (6 lectures)

Physical Aspects of Organic Chemistry: Factors which drive organic reactions: Isotope effects, Hammett Equation, Rate Equations and Organic Thermodynamics. (5 lectures)

Brief description of teaching and learning methods:

Approximately three one-hour lectures per week with tutorial or workshops to embed lecture content. Online testing will be used to assess understanding of individual topics.Ìý