CH2OR1NU-Further Organic Chemistry
Module Provider: Chemistry
Number of credits: 20 [10 ECTS credits]
Level:5
Terms in which taught: Autumn / Spring term module
Pre-requisites:
Non-modular pre-requisites: Available only to students on the BSc Applied Chemistry programme
Co-requisites:
Modules excluded:
Current from: 2021/2
Module Convenor: Dr John McKendrick
Email: j.e.mckendrick@reading.ac.uk
Type of module:
Summary module description:
This module intends to extend organic chemistry in the topics of carbonyl chemistry, radical chemistry, pericyclic reactions, etc.
Module Lead: Ying Li (yingliubc@qq.com)
Aims:
To understand basic concepts of organic chemistry with a more detailed and specific treatment of selected topics.
Assessable learning outcomes:
By the end of the module, it is expected that students will be able to:
- Master the related reaction of carbonyl groups, radicals, and organometallics.
- Be capable of unraveling organic conversions in the perspective of mechanisms.
- Be able to apply the reactions learnt and propose a synthetic route to synthesize simple organic compounds.
- Further understand conformation and its application in organic chemistry
- Be able to study reactions from the perspective of physical organic chemistry via isotope effect, electronic effect, thermodynamics, etc.
Additional outcomes:
By the end of the module, it is expected that students should be able to solve complicated organic problems.
Outline content:
Further Carbonyl Chemistry (10 Lectures)
Revision of carbonyl as electrophiles- nucleophilic addition and acyl nucleophilic substitution (1 lecture)
Revision of alpha-acidity of carbonyl compounds. & Revision of enolate chemistry: alkylation, alpha-halogenation, aldol condensation reaction, crossed aldol condensations, and Hell-Valhard Zelinsky reaction (2 Lectures)
Claisen condensation (1 lecture)
Dieckmann condensat ion (1 lecture)
the use of 1,3-dicarbonyl compounds (2 lectures)
decarboxylation of 1,3-keto-acids (1 lecture)
Michael addition reactions (1 lecture)
Robinson annulation (1 lecture)
Organometallics (7 Lectures)
Nucleophilic organometallic
Preparation of organometallic reagents; basic aspects of preparative carbanion chemistry.
Side reactions of organometallics
Addition to carbonyl compounds and acid derivatives and other electrophiles
Radical Reactions in Synthesis (7 Lectures)
The properties and use of free radicals in synthesis will be discussed. Areas covered will include radical substitution (revision) including the Bu3SnH processes, radical addition reactions, radical cyclization. Tandem radical reactions, the acyloin reaction and the Birch reduction.
Conformational Analysis (6 Lectures)
Differences between conformational and configurational isomers;
Conformation of acyclic molecules: staggered and eclipsed forms of ethane; butane and butane derivatives;
Conformation of cyclic systems: small, normal, medium and large rings; entropy and enthalpy factors in ring formations; conformational isomerization in cyclohexane and relationship to reactivity; decalin systems and steroids
Anomeric effect in conformation
Application of such conformation in reactions
Synthesis of Alicyclic Compounds (5 Lectures)
The methods available for the synthesis of small, medium and large carbo- and hetero-cyclic rings will be outlined, with suitable examples.
Molecular Rearrangements (8 Lectures)
Topics covered will include the Beckmann, pinacol, Curtius, Hofmann, Baeyer-Villiger and Lossen r
earrangements and their use for the synthesis of molecules of industrial importance.
Physical Aspects of Organic Chemistry (5 Lectures)
Factors which drive organic reactions: Isotope effects, Hammett Equation, Rate Equations and Organic Thermodynamics.
Brief description of teaching and learning methods:
The module includes blended teaching and workshops, involving intensive practice
| Autumn | Spring | Summer | |
| Lectures | 48 | 48 | |
| Guided independent study: | 52 | 52 | |
| Total hours by term | 100 | 100 | 0 |
| Total hours for module | 200 |
| Method | Percentage |
| Written exam | 60 |
| Written assignment including essay | 30 |
| Class test administered by School | 10 |
Summative assessment- Examinations:
Two 2-hour exams (one at the end of each semester)
Summative assessment- Coursework and in-class tests:
Workshop and assignments 30%
2x Mid term tests 10%
Formative assessment methods:
In the module students do the quiz in terms of topics.
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.
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:
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: None
2) Specialist equipment or materials: None
3) Specialist clothing, footwear or headgear: None
4) Printing and binding: None
5) Computers and devices with a particular specification: None
6) Travel, accommodation and subsistence: None
Last updated: 28 July 2021
THE INFORMATION CONTAINED IN THIS MODULE DESCRIPTION DOES NOT FORM ANY PART OF A STUDENT'S CONTRACT.