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CH20149: Organic synthesis, reaction mechanisms and spectroscopy

[Page last updated: 20 April 2021]

Academic Year: 2021/2
Owning Department/School: Department of Chemistry
Credits: 12      [equivalent to 24 CATS credits]
Notional Study Hours: 240
Level: Intermediate (FHEQ level 5)
Period:
Academic Year
Assessment Summary: EX 100%
Supplementary Assessment:
CH20149 Supplementary Assessment (where allowed by programme regulations)
Requisites: In taking this module you cannot take CH20150
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.

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

Content: 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.

Programme availability:
NB. Postgraduate programme information will be added when the postgraduate catalogues are published in August 2021

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)

Notes:

  • This unit catalogue is applicable for the 2021/22 academic year only. Students continuing their studies into 2022/23 and beyond should not assume that this unit will be available in future years in the format displayed here for 2021/22.
  • Programmes and units are subject to change 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.
  • Find out more about these and other important University terms and conditions here.