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CH20149: Organic synthesis, reaction mechanisms and spectroscopy

Follow this link for further information on academic years Academic Year: 2014/5
Further information on owning departmentsOwning Department/School: Department of Chemistry
Further information on credits Credits: 12
Further information on unit levels Level: Intermediate (FHEQ level 5)
Further information on teaching periods Period: Academic Year
Further information on unit assessment Assessment Summary: EX 100%
Further information on unit assessment Assessment Detail:
  • S1 Examination (EX 20%)
  • S2 Examination (EX 80%)
Further information on supplementary assessment Supplementary Assessment: CH20149 - Reassessment (where allowed by programme regulations)
Further information on requisites Requisites: Before taking this unit you must take CH10135 and while taking this unit you must take CH20147 and take CH20151 and in taking this unit you cannot take CH20150
Further information on descriptions Description: Aims:
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.

Learning Outcomes:
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.

Problem solving (T, F, A); Data Analysis (T, F, A); Independent working (F); Group working (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. Syntheis 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.
Further information on programme availabilityProgramme availability:

CH20149 is Compulsory on the following programmes:

Department of Chemistry
  • USCH-AFB01 : BSc(Hons) Chemistry (Year 2)
  • USCH-AAB02 : BSc(Hons) Chemistry with Study year abroad (Year 2)
  • USCH-AFM02 : MChem(Hons) Chemistry (Year 2)
  • USCH-AAM03 : MChem(Hons) Chemistry with Study year abroad (Year 2)
  • USCH-AFB07 : BSc(Hons) Chemistry for Drug Discovery (Year 2)
  • USCH-AAB08 : BSc(Hons) Chemistry for Drug Discovery with Study year abroad (Year 2)
  • USCH-AFM05 : MChem(Hons) Chemistry for Drug Discovery (Year 2)
  • USCH-AAM06 : MChem(Hons) Chemistry for Drug Discovery with Study year abroad (Year 2)
  • USCH-AKB08 : BSc(Hons) Chemistry for Drug Discovery with Industrial Placement (Year 2)
  • USCH-AKM03 : MChem(Hons) Chemistry for Drug Discovery with Industrial Placement (Year 2)
  • USCH-AFB09 : BSc(Hons) Chemistry with Education (Year 2)
  • USCH-AKB02 : BSc(Hons) Chemistry with Industrial Placement (Year 2)
  • USCH-AKM02 : MChem(Hons) Chemistry with Industrial Placement (Year 2)

* This unit catalogue is applicable for the 2014/15 academic year only. Students continuing their studies into 2015/16 and beyond should not assume that this unit will be available in future years in the format displayed here for 2014/15.
* Programmes and units are subject to change at any time, in accordance with normal University procedures.
* Availability of units will be subject to constraints such as staff availability, minimum and maximum group sizes, and timetabling factors as well as a student's ability to meet any pre-requisite rules.