Module proposal
UNIVERSITY OF WARWICK
Proposal Form for New or Revised Modules (MA1- version 3)
For consideration by the Undergraduate Studies Committee/Sub-Faculty or Graduate
Studies Committee only.
NB:
1.
If it is unclear whether or not a change to an existing module should be
proposed on this form, the Chair or Secretary of the Undergraduate
Studies Committee/Sub-Faculty or Graduate Studies Committee should
be consulted.
2.
In order to reduce printing costs please delete the text provided as
guidance in the body of the form before submission to the Faculty
Secretariat. However, all sections must be completed to the satisfaction of
the Faculty Undergraduate/Graduate Studies Committee.
1.
Title of Module:
CH248 Organic Synthesis
2.
New or Revised Module:
New module?
[]
Revised module?
[X]
Level: D (Doctorate)
M (Masters)
H (Honours)
I (Intermediate)
C (Certificate)
[ ]
[ ]
[X]
[ ]
[ ]
If this new module replaces an existing approved module specify the code and
title of the module to be discontinued and date on which change will occur:
If this is a proposal for a revised module, specify which sections have been
amended, and give an outline rationale for the changes:
Syllabus has been changed slightly in line with restructured first year
3.
Date of Introduction of new module or revised version of existing module:
October 2009
4.
Department Responsible for Teaching:
Chemistry
If the module is taught by more than one department please indicate this (for
matrix purposes):
Department
Department
%
%
Name of Module Leader:
Prof Mike Shipman
1
Module proposal
If the module leader is not a member of Warwick staff and has not previously
been appointed as a module leader/tutor, please include a C.V with this form.
5.
Availability/Location of module within courses:
List the degree courses on which this module is available, indicating the year of
study, whether the module is core or an option and the credit weighting in each
case. Include any part-time or 2+2 degrees on which this module is available.
Degree
Code
F100
F101
F102
F105
F106
F107
F108
F121
F122
F125
F126
F127
F128
BF91
B9F1
FC11
F1C1
Title
Chemistry BSc
Chemistry BSc with Intercalated year
General Chemistry BSc
Chemistry MChem
Chemistry MChem with Professional Experience
Chemistry MChem with Intercalated Year
Chemistry MChem with Industrial Training
Chemistry with Medicinal Chemistry BSc
Chemistry with Medicinal Chemistry BSc with
Intercalated Year
Chemistry with Medicinal Chemistry MChem
Chemistry with Medicinal Chemistry MChem with
Professional Experience
Chemistry with Medicinal Chemistry MChem with
Intercalated Year
Chemistry with Medicinal Chemistry MChem with
Industrial Training
Biomedical Chemistry BSc
Biomedical Chemistry BSc with Intercalated Year
Chemical Biology MChem
Chemical Biology MChem with Intercalated Year
Visiting Students
Year of
study
2
2
2
2
2
2
2
2
2
Core Optional Option list CATS*
core?
A,B or C
Core
7.5
Core
7.5
Core
7.5
Core
7.5
Core
7.5
Core
7.5
Core
7.5
Core
7.5
Core
7.5
2
2
Core
Core
7.5
7.5
2
Core
7.5
2
Core
7.5
2
2
2
2
Core
Core
Core
Core
7.5
7.5
7.5
7.5
7.5
*Credit should be in one of the following tariffs:
6, 12, 18, 24, 48 credits; or
7.5, 15, 30, 45, 60 credits; or
(for postgraduate courses only) 10, 20, 30, 40, 50,60 credits
6.
Consultation with other Departments:
It is important that any departments affected by the introduction of this
module are consulted before the module is considered by the relevant
Faculty committee.
Which other departments will be affected by the introduction/revision of this
module (i.e. other departments offering the module as an option in their degree
courses, including joint degree courses involving the department proposing the
module)? Please give details of any consultations undertaken and indicate
whether the other departments have approved the proposal.
Not applicable
2
Module proposal
7.
Context:
Describe the relationship to any other modules with which the new module has a
close connection and any prerequisite relationships.
CH161 Introduction to Organic Chemistry is a pre-requisite
8.
Module Aims:
These should identify the module’s broad educational purposes. Indicate how the
module will contribute to the achievement of the aims of the degree courses on
which it is available.
To provide a framework in which students are able to:
(i) consolidate existing knowledge and understanding of organic chemical transformations;
(ii) critically evaluate a proposed synthesis;
(iii) design a sensible synthesis of a given target molecule from readily available starting materials
9.
Learning Outcomes:
Successful completion of the module leads to the learning outcomes. The
learning outcomes identify the knowledge, skills and attributes developed by the
module. Learning Outcomes should be presented in the following format using
the table below:
By the end of the module students should be able to...
Learning Outcomes should include reference to subject knowledge and
understanding, key skills, cognitive skills and subject-specific practical and
professional skills and be clearly relevant to fulfilling the educational aims.
Learning Outcomes should be measurable by the assessment methods for the
module. Indicate how the module will contribute to the achievement of degree
course learning objectives.
(a)
Subject knowledge and understanding
The knowledge and understanding that a student will be expected to have
upon completion, such as : ‘a theoretical knowledge of the principles and
methods of archaeology’ or ‘a knowledge of the major types of chemical
reaction and the main characteristics associated with them.’
(b)
Key Skills
Communication (written, verbal, graphical...)
Numeracy
Use of information technology (e.g. WP, www, databases, spreadsheets,
specialist packages)
Ability to learn
Others (e.g. teamwork)
(c)
Cognitive Skills
For example: ability in critical analysis; the ability to formulate and test
concepts and hypotheses.
(d)
Subject-Specific/Professional Skills
For example: laboratory skills; scientific support writing; research skills
and methods.
3
Module proposal
LEARNING OUTCOMES
(By the end of the module the student should
be able to....)
Which teaching and learning methods enable
students to achieve this learning outcome?
Which assessment methods will measure the
achievement of this learning outcome?
....have a solid grounding of the mechanisms of a
wide range of organic chemical reactions.
.
Directed reading, lectures, tutorials.
formative assessment by set and marked work for
tutorials
summative assessment by examination
....understand and apply a wide range of important
chemical transformations of use in modern organic
synthesis. This will entail exposure to a significant
number of new reactions as well as revision and
further application of important organic reactions
seen in year 1.
Lectures, tutorials, workshops.
formative assessment by set and marked work for
tutorials
summative assessment by examination
....justify their solutions to problems in organic
chemistry.
Lectures, tutorials, workshops..
formative assessment by set and marked work for
tutorials and examples classes
summative assessment by examination
4
Module proposal
10.
Syllabus:
Give an outline of the syllabus for the module.
A. INTRODUCTION AND CONTEXT
B. MAKING C–C BONDS
B.1 Using Organometallics
Organolithium Reagents. Formation by deprotonation, oxidative insertion, halogen-metal exchange.
Useful C–C bond forming reactions with carbon dioxide, aldehydes/ketones, carboxylic acids, use of
1,3-dithianes.
Grignard Reagents. Synthesis by insertion. Reactions with formaldehyde, aldehydes and ketones,
esters, nitriles, addition to enones in absence/presence of Cu(I).
Organozinc Reagents. Reformatsky reaction.
Organocopper Reagents. Synthesis by transmetallation. Use in conjugate additions, SN2displacements, epoxide openings and alkylation of acid chlorides.
B.2 Using Enolates
Enolate formation using strong bases, C- vs O-alkylation, thermodynamic vs kinetic enolate formation,
alkylation of enolate anions, crossed-aldol reactions, stereocontrolled aldols with E- and Z-lithium and
boron enolates, Zimmerman-Traxler transition states. Alternatives to enolates: enamines and silyl enol
ethers (Mukaiyama aldol). Use of enolates to make rings: Dieckmann reaction, Robinson annulation.
C. MAKING C=C AND C≡C BONDS
C.1 Formation of C=C Bonds
Wittig reaction including: formation of phosphonium ylids, cycloaddition mechanism, reactivity
comparison with sulfur ylids, E-alkenes from stabilised ylids, Z-alkenes using non-stabilised ylids.
Alternatives to the Wittig reaction including (i) Horner-Wadsworth-Emmons reaction to make Ealkenes, use of Arbuzov reaction to make phosphonate esters; (ii) Peterson reactions under acidic and
basic conditions, (iii) Julia reaction of sulfone anions. Use of elimination reactions to make alkenes
including (i) dehydrations; (ii) pyrolytic syn-eliminations involving esters, N-oxides, sulfoxides and
selenoxides; (iii) from 1,2-diols (Corey-Winter).
C.1 Formation of C≡C Bonds
Corey-Fuchs reaction.
D. FUNCTIONALISATION OF ALKENES
Oxymercuration/reduction. Hydration by hydroboration including mechanism, stereochemical issues,
improved regio- and chemoselectivity with 9-BBN. Synthesis of C–C and C–N bonds using
organoboranes.
E. OXIDATION
E.1 Oxidation of Allylic C-Bonds
Using selenium dioxide and singlet oxygen.
E.2 Important Methods for the Oxidation of Alcohols
Jones oxidation, PCC including allylic transposition with tertiary allylic alcohols, manganese dioxide
for selective oxidation of allylic/benzylic alcohols, Dess-Martin periodinane, DMSO based oxidations
including Swern and Corey-Kim procedures. DMSO based oxidation of C–X bonds.
E.3 Oxidative Cleavage of Diols.
Using NaIO4 and cat. OsO4/NaIO4 (cf ozonolysis).
F. REDUCTION
F.1 Reduction of C=O and C=N Bonds
Reduction of esters using lithium aluminium hydride and DIBAL, reduction of carboxylic acids using
borane, use of sodium borohydride to reduce aldehydes/ketones, ‘exhaustive’ reduction of ketones to
alkanes using (i) Clemmensen reduction; (ii) Wolff-Kishner; and (iii) dithioacetal reduction, reduction
of amides using LiAlH4 and borane, use of azides to make amines, reduction of C=N bonds using
sodium cyanoborohydride.
F.2 Reduction of C–X Bonds
Reduction of halides and pseudohalides with LiAlH4, use of Appel reaction to prepare halides from
alcohols.
5
Module proposal
11.
Illustrative Bibliography:
List the core texts only. The illustrative bibliography should provide an
indication of the focus and level of the reading required by this module, rather
than the full range (this should not be more than half a page):
Clayden, Greeves, Warren & Wothers ‘Organic Chemistry’
12.
Teaching:
Give the number of each type of teaching event per week and the length of
each session in hours.
Lectures per week (5 weeks)
Workshops
Tutorials
Private/self study
Total contact hours
Module duration (weeks, if applicable)
13.
Assessment Methods:
Type of assessment
Length
Examinations
Assessed essays/ coursework
Other type of formal assessment
14.
3 hrs per week (15 hrs in total)
Revision session (1 hr)
2 hrs in total
57 hrs in total
75 hours
5 weeks
1.5
hour
paper
N/A
N/A
% weighting
100%
N/A
N/A
Resources:
Are any resources required for this module which are not already available
from the Department’s own baseline resources (e.g. staff costs,
accommodation, equipment, minor works, library costs, audio visual and
computing facilities, vacation study requirements)? Is the module likely to
require high usage of centrally timetabled teaching rooms or specific slots
(e.g. for a module on a part time postgraduate course)?
Any additional requirements should be discussed with the appropriate Officer
(see list below) before submitting the proposal.
List any additional requirements and indicate the outcome of any discussions.
None
Signature of Module Leader:
Prof Mike Shipman
Date
12 Sept 2011
Signature of Chair of Department:
6
Module proposal
Date
7
Exams Office
Assessment Details (information required by the Exams Office)
This form should be completed only for modules to be assessed by an exam organised by the Exams Office
The form does not have to be submitted for approval but should be sent to Andrea Humber in the Exams
Office. If this information is not provided the module cannot be set up on the Student Record System and
students will therefore be unable to register for the module and exam. If you have any queries about this
form please contact Andrea Humber in the Examination Office (ext 74160)
Module Title
Department
Module Leader
Name of Examiner
CH248 Organic Synthesis
Chemistry
Prof Mike Shipman
Indicate all available methods of assessment in the table below
% Examined
% Assessed by other methods
100%
Length of examination paper
1.5hrs
Examination Details
Will this module be examined together with any other module (sectioned paper)? If so please give details.
Yes it will be examined along with the new module CH269 Introduction to Biological and Medicinal
Chemistry (3hr paper in total)
Is the module to be examined by 1 paper
[X ]
or 2 papers
[ ]
When will the exam take place (e.g. Jan, April, Summer)? . .summer . . . . . . . . . . . . . . . . .
Is reading time required?
Yes [ ]
No [ ]
Give any special exam timetable arrangements
Stationery Requirements
No. of Answer Books
Graph Paper
Calculator
List any other special stationery requirements (e.g. Data books, tables etc):
Type of Paper
Seen:
Yes [ ] No [ ]
Open Book : Yes [ ] No [ ]
Restricted:
Yes [ ] No [ ]
Where restricted please provide list of texts permitted here:
8