Department of Chemistry, Unit Catalogue 2011/12
|Level:||Intermediate (FHEQ level 5)|
|Assessment:||EX 80%, PR 20%|
|Supplementary Assessment:||CH20150 - Reassessment Examination (where allowed by programme regulations)|
|Requisites:||Before taking this unit you must take CH10136 and in taking this unit you cannot take CH20149|
To provide the student with a working knowledge of important classes of organic transformations and illustrate how the rate and mechanism of a chemical reaction can be understood in terms of the chemical structure of molecules. To give an overview of retrosynthetic analysis as a valuable method for the design of an organic molecule. To show how experimental kinetic data may be used to elucidate chemical reaction mechanisms.
After studying this Unit, students should be able to:
* interpret and predict NMR spectra and mass spectra
* account for the importance of stereoselectivity in organic synthesis.
* demonstrate the important relationship between structure and reactivity for organic molecules.
* design syntheses of heterocyclic and alicyclic compounds from common starting materials
* apply retrosynthesis methods to a selected range of compounds
* Describe the synthetic chemistry of carbocations, anions and radical species and describe some of the mechanisms involved in their reaction.
* analyse experimental rate data for first- and second-order reactions;
* describe how the involvement of a reaction intermediate may be deduced;
* discuss the stereochemistry of aliphatic nucleophilic substitution;
* describe the effects of added ions upon SN1 substitutions;
* discuss the role of ion pairs in unimolecular solvolyses;
* determine the pH of a buffer solution;
* describe the effect of pH on the rates of acid or base catalysed reactions;
* distinguish general catalysis from specific catalysis by acids or bases;
* describe the features of nucleophilic catalysis.
* Rationalise the reactivity of molecules using stereoelectronic principles
* To recognise the relationship of the experiments to the lecture material.
* To interpret spectroscopic data of a wide variety and to relate this to the spatial, structural and chemical features of the compounds synthesised in the laboratory.
* To apply their experience in synthetic organic chemistry to other organic reactions.
* To demonstrate their practical skills and techniques to a good level of ability.
* To give an oral presentation based on an experiment performed in the laboratory.
Problem solving (T, F, A); Data Analysis (T, F, A); Independent working (F); Group working (F); Scientific writing (F, A); Oral communication (F).
Interpretation of NMR spectra including homotopic and diastereotopic protons. Correlation spectroscopy. Mass spectrometry. The principles of retrosynthesis. The use of carbon nucleophiles in retrosynthesis. Malonate ester synthesis and applications. Umpolung reagents. Alkene synthesis, including Wittig reaction. Oxidation reactions of alkenes and alcohols. Reduction reactions of ketones and other carbonyl compounds. Review of aromatic chemistry. Description, reactivity and synthesis of heterocycles including pyrroles, furan, thiophene, pyridine and indoles. Synthesis and reactivity of naphthalene, quinolines and isoquinolines. Concepts of organopalladium chemistry. Concepts of combinatorial chemistry for the synthesis of libraries of heterocycles. Aliphatic nucleophilic substitution: 1st & 2nd order kinetics, competing reactions; Deduction of reaction mechanism, evidence for intermediates; Stereochemical evidence for the SN2 mechanism; Evidence for the SN1 mechanism: consecutive reactions, common-ion effect, solvolysis, ion pairs; Acid/base catalysis: solvent levelling, buffers, specific & general catalysis; Nucleophilic catalysis. Review of basic stereochemistry principles. The importance of stereoselective synthesis. Diastereomers and diastereoselective synthesis. Conformation of cyclohexanes - the importance of stereochemistry to reactivity - carbohydrates. Stereochemistry and mechanism. Frontier Molecular Orbital Theory and stereoelectronic effects. Aspects of the chemistry of carbocations, carbanions, radicals, carbenes, nitrenes, and arynes. Experiments designed to illustrate the wide diversity of organic chemistry ranging from physical principles to organic synthesis and through to biological and natural product chemistry. These experiments will extend existing, and introduce new, skills and techniques to the students.
CH20150 is Compulsory on the following programmes:Department of Chemistry
CH20150 is Optional on the following programmes:Programmes in Natural Sciences