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: CH1OC2 Shape, Structure and Reactivity in Organic Chemistry
Non-modular pre-requisites:
Co-requisites:
Modules excluded:
Current from: 2023/4

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 students' 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

Contact hours:

Ìý	Autumn	Spring	Summer
Lectures	11	21
Seminars	2	4	6
Supervised time in studio/workshop	2	2
Guided independent study:	45	73	34
Ìý	Ìý	Ìý	Ìý
Total hours by term	60	100	40
Ìý	Ìý	Ìý	Ìý
Total hours for module	200

Summative Assessment Methods:

Method	Percentage
Written exam	80
Set exercise	20

Summative assessment- Examinations:

A two-hour examination during the Summer Term based upon lecture, tutorial and workshop material.

The examination for this module will require a narrowly defined time window and is likely to be held in a dedicated exam venue.

Summative assessment- Coursework and in-class tests:

Four on-line tests (best four out of five each weighted at 5%; total contribution to module mark from tests is 20%): Students will be required to undertake short Blackboard tests relating to the lecture material.

Formative assessment methods:

Students attend tutorials and workshops on the material covered in this module. Attendance is compulsory at both, failure to attend will play a part in the triggering of the Universities academic non-engagement process. Workshops build on lecture material and encourage students to think about the lecture material in context and apply this knowledge to unseen problems; workshop problems provide good practice for the end of year examination.

Penalties for late submission:

The Support Centres will apply the following penalties for work submitted late:

• where the piece of work is submitted after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for that piece of work will be deducted from the mark for each working day (or part thereof) following the deadline up to a total of five working days;
• where the piece of work is submitted more than five working days after the original deadline (or any formally agreed extension to the deadline): a mark of zero will be recorded.

The University policy statement on penalties for late submission can be found at: /cqsd/-/media/project/functions/cqsd/documents/cqsd-old-site-documents/penaltiesforlatesubmission.pdf
You are strongly advised to ensure that coursework is submitted by the relevant deadline. You should note that it is advisable to submit work in an unfinished state rather than to fail to submit any work.

Assessment requirements for a pass:
A mark of 40% overall

Reassessment arrangements:

Reassessment arrangements are in accordance with University policy. Reassessment of the written examination is held during the University-administered re-examination period in August. Failed coursework may be re-assessed by an alternative assignment before or during the August re-examination period.

Additional Costs (specified where applicable):

1) Required text books:Ìý Organic Chemistry by Clayden, Greeves and Warren, Oxford University Press

2) Specialist equipment or materials:ÌýÌý

3) Specialist clothing, footwear or headgear:ÌýÌý

4) Printing and binding:Ìý Printing of notes using university printers is expensive. Lecture notes are available in electronic form on Blackboard and will cost <£10 to print out if desired.

5) Computers and devices with a particular specification:ÌýÌý

6) Travel, accommodation and subsistence:ÌýÌý

Last updated: 27 November 2023