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CH403 Organic Chemistry CH403 Organic Chemistry Basics UG/PG/CE: Undergraduate Semester: Semester 1 2008/2009 Strathclyde Standard 2003 Scheme: Credits: 10 Level: Level 4 and after NE - Not Offered As An Location: John Anderson Elective: Elective Mode Of Attendance Delivery: Department: Pure And Applied Chemistry Faculty: Faculty Of Science Credit Rating Equivalence Credit Scheme Credits Level European Credit Transfer Scheme 5 Not Applicable Strathclyde Standard 2002 and before 1 Advanced Teaching Components Timetabled Components - ACADEMIC YEAR 2008/2009 NB: Lecture details are shown below, attendance at practical and/or tutorial events may also be required. Activity Type Component Lecture A It is assumed that a student will participate in one offering (series) of each of the above components. Teaching Component Offering Times Lectures Component Series Day Start End Weeks Building Room A 1 Tuesday 12:00 13:00 wk 1-23 THOMAS GRAHAM C61 A 1 Thursday 12:00 13:00 wk 1-23 THOMAS GRAHAM C61 NB: Rooms and times are subject to change. Staff Contact: Dr Debra Willison, PURE AND APPLIED CHEMISTRY Organiser: Dr Debra Willison, PURE AND APPLIED CHEMISTRY Overview Aims: To survey some of a series of contemporary organoelemental techniques that have been developed for use in organic synthesis. To highlight a further selection of developing methods and strategies in organic chemistry and to link the new synthetic methods to both mechanistic understanding and the practical processes employed. To reinforce the use of retrosynthetic analysis as a method by which organic synthesis can be planned and, in so doing, show how the use of the delineated techniques can be embedded within synthetic pathways. To examine the use of these techniques and strategies, where they have been applied, in target molecule synthesis. To apply the techniques being covered within chemical problem solving sessions. To discuss prostereoisomerism and outline the nomenclature protocols. To exemplify prostereoisomerism in enzymatic processes. To detail stereoselective and stereospecific processes. Briefly overview thermodynamic principles of selectivity. Briefly overview methods of measuring chirality. Syllabus Topics 1-8 Use of Organoelemental Reagents in Synthesis This will expand on the introduction to this general area as covered in the 3rd Year and will include more advanced aspects of organoboron chemistry (e.g. carbonylation reactions and use of alkynes), organosilicon chemistry (e.g. further use of allyl and vinyl silane [including aspects of regio-and stereoselectivity], organophosphorus chemistry (e.g. E- and Z-selective olefinations, conversion of aldehydes to alkynes), orgnosufur chemistry (e.g. selectivity in use of sulfonium ylides and Shapiro- type processes), and organoselenium chemistry. Within this area and as part of the problem solving sessions, aspects of retrosynthetic analysis using these and other (previously covered) reagents will be embedded within the lectures. 9-12 Contemporary Reagents for Use in Synthesis. Alternative contemporary alkene forming processed and a range of selective oxidation and reduction processes will be delineated. The synthetic methods will be linked to mechanistic understanding and the practical techniques used. Again, problem solving sessions will illustrate how these (and previously covered) techniques can be used in synthetic organic sequences. 12-17 Overview of techniques for studying organic reaction mechanisms. Product studies, stereochemical outcomes, isotopic labelling, kinetic measurements, chemical and physical trapping of intermediates and the Favorskii rearrangement, photochemical intermediates and matrix isolation. Frontier Orbital Theory, Woodward-Hoffmann Rules, pericyclic reactions: cycloadditions, sigmatropic and electrocyclic reactions. 18-20 Re-introduction of chirality and prostereoisomerism discussed in terms of hydride addition to prochiral and chiral carbonyl compounds and some basic definitions (ee, dr, de, kinetic resolution). Selectivity and Specificity: Steric & co-ordination control, mechanistic control, stereoelectronic control (Felkin Ahn and chelation models, relative topicity) thermodynamic/kinetic control. Thermodynamic principles of selectivity. Measurement of chirality, polarimetry NMR shift reagents and chromatography. Learning Outcomes Learning Outcomes: Level 4 To develop an understanding of the mechanism and reactivity principles involved in the use of more advanced organoelemental reagents (including organoboron, -silicon, -phophorus, ?sulfur, and ?selenium compounds). To develop an understanding of the regio- and stereoselectivity that can be achieved in organic synthesis by the use of such organoelemental methods. To establish an understanding and awareness of the continually evolving nature of organic chemistry by the introduction of new and developing methods in organic chemistry (e.g. mild and selective oxidations and reductions, emerging olefination techniques, and hypervalent-iodide derived methods). To build a knowledge base of the chief characteristics of such organoelemental species and other contemporary reagents that overlays the knowledge base obtained from earlier stages of the chemistry course and, in particular, that covered in Year 3 (and 4). To develop an understanding of the mechanism and reactivity principles involved in the use of the new and developing methods and to establish the levels of selectivity that can be achieved by the use of such techniques. To develop problem solving abilities in a range of synthetic contexts by applying the advanced preparative techniques delineated as part of this programme. To further extend and develop an understanding of the transferable principles of organic chemistry, in particular with regards synthetic strategies involving polyfunctional molecules. To further develop the application of knowledge and understanding to the solution of problems and to the prediction of chemical properties of previously unseen compounds or reactions. Be able to assign prostereoisomeric groups and faces using stereochemical nomenclature. Be aware of the methods of controlling stereoselective and stereospecific processes and be able to apply these to synthetic transformations. Understand the thermodynamic principles of selectivity. Be aware of the methods of measuring chirality with an appreciation of the advantages/disadvantages of each method. Level 5 To develop abilities to establish an appreciation of a range of distinct reagents and techniques that have the abilities to perform similar synthetic transformations and, by taking an overview, to develop the abilities to discern the comparative advantages and disadvantages of the individual reagents and techniques. For a given synthetic transformation or series of transformations, to develop the abilities to reason whether a given reagent/technique or reagents/techniques would be used over alternative reagents or methods. To develop a proficiency in manipulating a variety of organic structural formulae with an emphasis on polyfunctional organic compounds. To further develop the application of knowledge and understanding to the solution of problems and to the prediction of chemical properties of previously unseen compounds or reactions. CH404 Cage And Cluster Molecules Basics UG/PG/CE: Undergraduate Semester: Semester 1 2008/2009 Strathclyde Standard 2003 Scheme: Credits: 5 Level: Level 4 and after NE - Not Offered As An Location: John Anderson Elective: Elective Mode Of Attendance Delivery: Department: Pure And Applied Chemistry Faculty: Faculty Of Science Credit Rating Equivalence Credit Scheme Credits Level European Credit Transfer Scheme 2.5 Not Applicable Strathclyde Standard 2002 and before .5 Advanced Teaching Components Timetabled Components - ACADEMIC YEAR 2008/2009 NB: Lecture details are shown below, attendance at practical and/or tutorial events may also be required. Activity Type Component Lecture A Lecture B It is assumed that a student will participate in one offering (series) of each of the above components. Teaching Component Offering Times Lectures Component Series Day Start End Weeks Building Room A 1 Wednesday 09:00 10:00 wk 7 THOMAS GRAHAM C61 A 1 Monday 09:00 10:00 wk 7-12 THOMAS GRAHAM C61 B 1 Friday 09:00 10:00 wk 7-12 THOMAS GRAHAM C61 NB: Rooms and times are subject to change. Staff Contact: Dr Debra Willison, PURE AND APPLIED CHEMISTRY Overview Aims To introduce students to the fundamental importance of cage and cluster molecules in chemistry. To gain an appreciation of the widespread importance of organolithium compounds as indispensable reagents for synthesis. To gain an understanding of the preparation, structural principles and general reaction chemistry of key cage and cluster molecules. Syllabus Topics 1-2 Basics of organolithium chemistry: general preparative methods; synthetic applications of and selectivity patterns of lithium alkyls, lithium amides, and mixed-metal superbases. 3-4 Principles of aggregation and solvation in organolithium compounds. Electron-deficient bonding, tetrameric and hexameric cages, polymers and other oligomers. Ring-stacking and ring-laddering. 5 Dynamic structures in solution. Structural rearrangements. The role of the metal in synthetic applications ? a case study of the aldol reaction. 6-7 Cluster molecules. Common geometries. Electron -precise, -deficient and -rich clusters. Boron hydride clusters. Electron-counting and Wade?s rules. Carborane and metallocarborane clusters. 8-9 Transition metal clusters. Osmium carbonyl species, high-nuclearity clusters,
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