2019/20 Undergraduate Module Catalogue
CHEM2241 Organic Structure and Mechanism
10 creditsClass Size: 170
Module manager: Dr Nimesh Mistry
Email: N.Mistry@leeds.ac.uk
Taught: Semester 2 (Jan to Jun) View Timetable
Year running 2019/20
Pre-requisite qualifications
Level 1 chemistry or equivalentPre-requisites
| CHEM2141 | Introduction to Organic Synthesis |
Module replaces
CHEM2340 Organic Structure, Mechanism and SynthesisThis module is not approved as a discovery module
Objectives
On completion of this module, students will:(a) understand the meaning and significance of conformation and configuration of organic compounds, and their influence on organic structure/reactivity (stereoelectronic effects);
(b) understand the stereochemical and regiochemical outcome of pericyclic reactions and be able to apply that knowledge in designing syntheses of organic molecules.
Learning outcomes
Conformational analysis; stereoelectronic effects in organic reaction mechanisms; stereochemical and regiochemical outcome of pericyclic reactions.
Syllabus
STEREOCHEMISTRY AND CONFORMATIONAL ANALYSIS
The difference between conformation and configuration. Newman projections. Chair conformations of 6-rings. 1,3-Diaxial interactions to determine conformation. Conformational analysis of cyclohexenes and cyclohexanonones. Use of NMR in determining favoured conformations. Enantiomers are non-superimposable mirror image compounds; same physical properties; examples to include S and P chiral centres cf. pyramidal inversion at N. Biaryl compounds – atropisomers.The difference between enantiomers and diastereoisomers. Homotopic, enantiotopic and diastereotopic groups - the substitution test. Diastereotopic groups can be distinguished in NMR spectra. Peptides and proteins: primary, secondary and tertiary structure; peptide synthesis and avoiding racemisation
STEREOELECTRONIC EFFECTS
Revision of SN2 in terms of * orbital - the overlap of filled and empty orbitals. * orbitals in reactions in which a bond is broken; E2. Use of Newman projections. The anomeric effect: kinetic and thermodynamic aspects. Epoxides and iodonium ions etc. have similar conformations to the parent alkenes. Transdiaxial opening of epoxides, iodonium ions etc; iodolactonisation. The Wittig reaction: explanation of the stereochemical aspects using Newman projections.
Rearrangements: Baeyer-Villiger, Beckmann, pinacol. Retention of configuration at the migratory origin, discussion in terms of orbitals.
PERICYCLIC REACTIONS
The Diels-Alder reaction. Stereospecificity: retention of diene and dienophile geometry. Stereoselectivity: the endo rule. Predicting the stereochemical outcome of Diels-Alder reactions. The ortho/para rule to predict regiochemistry. Ozonolysis; use to make 1,6-dicarbonyl compounds from six-membered rings. Other 1,3-dipolar cycloadditions, eg SPAAC.
Sigmatropic rearrangements, eg Claisen and Cope. Electrocyclic reactions. Ring opening and closing reactions. Conrotatory and disrotatory mechanisms.
Teaching methods
| Delivery type | Number | Length hours | Student hours |
| Lectures | 22 | 1.00 | 22.00 |
| Seminar | 2 | 1.00 | 2.00 |
| Tutorial | 2 | 1.00 | 2.00 |
| Private study hours | 74.00 | ||
| Total Contact hours | 26.00 | ||
| Total hours (100hr per 10 credits) | 100.00 | ||
Private study
75 hours = Preparation of written work for tutorials. Reading for lectures and workshops.Opportunities for Formative Feedback
Progress monitored by lecture attendance, contributions in tutorials, tutorial work.Methods of assessment
Coursework
| Assessment type | Notes | % of formal assessment |
| Tutorial Performance | Assessment of tutorial work | 6.00 |
| Tutorial Performance | Assessment of tutorial work | 6.00 |
| Total percentage (Assessment Coursework) | 12.00 | |
Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated
Exams
| Exam type | Exam duration | % of formal assessment |
| Standard exam (closed essays, MCQs etc) | 2 hr 00 mins | 88.00 |
| Total percentage (Assessment Exams) | 88.00 | |
Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated
Reading list
The reading list is available from the Library websiteLast updated: 05/11/2019 08:50:00
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