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CH20149: Organic synthesis, reaction mechanisms and spectroscopy

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 0%, EX-TH 100%*
Further information on unit assessment Assessment Detail:
  • S1 Mock Exam* (EX 0%)
  • S2 Open Book Examination of 24 hours duration* (EX-TH 100%)

*Assessment updated due to Covid-19 disruptions
Further information on supplementary assessment Supplementary Assessment:
CH20149 Supplementary Assessment (where allowed by programme regulations)
Further information on requisites Requisites:
In taking this module 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:
* apply retrosynthesis methods to a selected range of compounds;
* design syntheses of heterocyclic and alicyclic compounds from common starting materials;
* interpret NMR spectra;
* deduce reaction mechanisms for aliphatic nucleophilic substitution from experimental rate data;
* recognise when a simple mechanism is inadequate to account for experimental observations;
* distinguish mechanisms for catalysis by acids, bases and nucleophiles;
* apply principles of conformational analysis and diastereoselectivity to account for selectivity in organic reactions;
* describe the role of orbitals in determining conformation and reactivity of organic molecules;
* describe the roles of reactive intermediate in organic synthesis.

Problem solving (T, F, A), Oral communication (F), Data analysis (T, F, A).

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.
Heteroaromaticity chemistry. Description, reactivity and synthesis of heterocycles including: pyrrole, pyridine, indole & quinoline. Application of organometallic chemistry to coupling reactions: Suzuki, Heck, etc. Azoles and metalation. Nucleophilic heteroaromatic substitution.
Interpretation of NMR spectra including chemical shift, spin-spin coupling and 2D NMR.
Kinetic and stereochemical evidence for SN1 and SN2 mechanisms of aliphatic nucleophilic substitution. Competing & consecutive reactions. Deduction of reaction mechanism & evidence for intermediates. Common-ion effect & ion pairs. Specific & general acid & base catalysis. Nucleophilic catalysis.
Conformational analysis and diastereoselectivity. Stereochemical principles. Alicyclic conformation, ring strain and reactivity. Diastereomers and diastereoselective synthesis, including Felkin-Anh model & chelation control in reactions of enolates.
Frontier Molecular Orbital Theory and stereoelectronic effects. Baldwin's rules. Pericyclic reactions.
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-AFB07 : BSc(Hons) Chemistry for Drug Discovery (Year 2)
  • USCH-AAB08 : BSc(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-AKB02 : BSc(Hons) Chemistry with Industrial Placement (Year 2)
  • USCH-AFM02 : MChem(Hons) Chemistry (Year 2)
  • USCH-AAM03 : MChem(Hons) Chemistry 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-AKM03 : MChem(Hons) Chemistry for Drug Discovery with Industrial Placement (Year 2)
  • USCH-AKM02 : MChem(Hons) Chemistry with Industrial Placement (Year 2)