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CH20150: Organic synthesis, reaction mechanisms and spectroscopy (NS/CwM)

Follow this link for further information on academic years Academic Year: 2019/0
Further information on owning departmentsOwning Department/School: Department of Chemistry
Further information on credits Credits: 12      [equivalent to 24 CATS credits]
Further information on notional study hours Notional Study Hours: 240
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 80%, PR 20%
Further information on unit assessment Assessment Detail:
  • S1 Mock Exam (EX 0%)
  • Practical (PR 19%)
  • Practical Attendance (PR 1%)
  • S2 Exam (EX 80%)
Further information on supplementary assessment Supplementary Assessment:
CH20150 Supplementary Assessment (where allowed by programme regulations)
Further information on requisites Requisites:
In taking this module you cannot take CH20149
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. The aim of the practical material is to extend and develop laboratory skills and techniques necessary for competent practical organic chemists. To complement some of the lecture material presented and to provide experience in synthetic organic chemistry and, in particular, spectroscopic interpretation of structural features of compounds. To provide the necessary key skills for the preparation and delivery of a short presentation based on an organic chemistry experiment.

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
* 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.

Skills:
Problem solving (T, F, A); Data Analysis (T, F, A); Independent working (F); Group working (F); Scientific writing (F, A); Oral communication (F).

Content:
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.
Further information on programme availabilityProgramme availability:

CH20150 is Compulsory on the following programmes:

Department of Chemistry
  • USCH-AFB03 : BSc(Hons) Chemistry with Management (Year 2)
  • USCH-AAB04 : BSc(Hons) Chemistry with Management with Study year abroad (Year 2)
  • USCH-AKB04 : BSc(Hons) Chemistry with Management with Industrial Placement (Year 2)
  • USCH-AFM07 : MSci(Hons) Chemistry with Management (Year 2)
  • USCH-AKM07 : MSci(Hons) Chemistry with Management with Industrial Placement (Year 2)

CH20150 is Optional on the following programmes:

Programmes in Natural Sciences
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Biochemistry with Chemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Biochemistry with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Biochemistry with Chemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Biochemistry with Pharmacology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Biochemistry with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Biochemistry with Pharmacology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Biology with Chemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Biology with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Biology with Chemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Biology with Pharmacology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Biology with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Biology with Pharmacology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Chemistry with Biochemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Chemistry with Biochemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Chemistry with Biochemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Chemistry with Biology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Chemistry with Biology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Chemistry with Biology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Chemistry with Pharmacology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Chemistry with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Chemistry with Pharmacology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Chemistry with Physics stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Chemistry with Physics stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Chemistry with Physics stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Environmental Science with Biochemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Environmental Science with Biochemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Environmental Science with Biochemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Environmental Science with Biology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Environmental Science with Biology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Environmental Science with Biology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Environmental Science with Chemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Environmental Science with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Environmental Science with Chemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Environmental Science with Physics stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Environmental Science with Physics stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Environmental Science with Physics stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Pharmacology with Biochemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Pharmacology with Biochemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Pharmacology with Biochemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Pharmacology with Biology stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Pharmacology with Biology stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Pharmacology with Biology stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Pharmacology with Chemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Pharmacology with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Pharmacology with Chemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Physics with Chemistry stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Physics with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Physics with Chemistry stream) with Year long work placement (Year 2)
  • UXXX-AFB01 : BSc(Hons) Natural Sciences (Physics with Environmental Science stream) (Year 2)
  • UXXX-AAB02 : BSc(Hons) Natural Sciences (Physics with Environmental Science stream) with Study year abroad (Year 2)
  • UXXX-AKB02 : BSc(Hons) Natural Sciences (Physics with Environmental Science stream) with Year long work placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Biochemistry with Chemistry stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Biochemistry with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Biochemistry with Chemistry stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Biochemistry with Pharmacology stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Biochemistry with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Biochemistry with Pharmacology stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Biology with Chemistry stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Biology with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Biology with Chemistry stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Biology with Pharmacology stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Biology with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Biology with Pharmacology stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Chemistry with Biochemistry stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Chemistry with Biochemistry stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Chemistry with Biochemistry stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Chemistry with Biology stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Chemistry with Biology stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Chemistry with Biology stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Chemistry with Pharmacology stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Chemistry with Pharmacology stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Chemistry with Pharmacology stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Chemistry with Physics stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Chemistry with Physics stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Chemistry with Physics stream) with Professional Placement (Year 2)
  • UXXX-AFM01 : MSci(Hons) Natural Sciences (Physics with Chemistry stream) (Year 2)
  • UXXX-AAM02 : MSci(Hons) Natural Sciences (Physics with Chemistry stream) with Study year abroad (Year 2)
  • UXXX-AKM02 : MSci(Hons) Natural Sciences (Physics with Chemistry stream) with Professional Placement (Year 2)

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