CH2OR1NU-Further Organic Chemistry

Module Provider: Chemistry
Number of credits: 20 [10 ECTS credits]
Level:5
Semesters in which taught: Semester 1 / 2 module
Pre-requisites:
Non-modular pre-requisites: Available only to students on the BSc Applied Chemistry programme
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:

This module intends to extend organic chemistry in the topics of carbonyl chemistry, radical chemistry, pericyclic reactions, etc.

Module Lead:ÌýÌýYing LiÌý(yingliubc@)

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:

• ÌýMaster 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 condensation (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)

OrganometallicsÌý(7 Lectures)

Nucleophilic organometallic

Preparation of organometallic reagents; basic aspects of preparative carbanion chemistry.

Sidereactions 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 AnalysisÌý (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 CompoundsÌý(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 RearrangementsÌý(8 Lectures)

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.

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

Contact hours:

Ìý	Semester 1	Semester 2
Lectures	48	48
Guided independent study:	52	52
Ìý	Ìý	Ìý
Total hours by term	100	100
Ìý	Ìý	Ìý
Total hours for module	200

Summative Assessment Methods:

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 assignmentsÌýÌýÌýÌýÌýÌýÌý 30%

2x Mid term testsÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌýÌý 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.

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:

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 None

2) Specialist equipment or materials:Ìý None

3) Specialist clothing, footwear or headgear:Ìý None

4) Printing and binding:Ìý None

5) Computers and devices with a particular specification:Ìý None

6) Travel, accommodation and subsistence:Ìý None

Last updated: 22 September 2022