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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 View Timetable

Year running 2019/20

Pre-requisite qualifications

Level 1 chemistry or equivalent

Pre-requisites

CHEM2141Introduction to Organic Synthesis

Module replaces

CHEM2340 Organic Structure, Mechanism and Synthesis

This 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 typeNumberLength hoursStudent hours
Lectures221.0022.00
Seminar21.002.00
Tutorial21.002.00
Private study hours74.00
Total Contact hours26.00
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 typeNotes% of formal assessment
Tutorial PerformanceAssessment of tutorial work6.00
Tutorial PerformanceAssessment of tutorial work6.00
Total percentage (Assessment Coursework)12.00

Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated


Exams
Exam typeExam duration% of formal assessment
Standard exam (closed essays, MCQs etc)2 hr 00 mins88.00
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 website

Last updated: 18/01/2019

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