ORGANIC CHEMISTRY 2

SHE Level 3
SCQF Credit Points 20.00
ECTS Credit Points 10.00
Module Code M3F121840
Module Leader Mark Spicer
School School of Computing, Engineering and Built Environment
Subject Chemical Science
Trimesters
  • A (September start)
  • A (September start)-B (January start)

Pre-Requisite Knowledge

M2F121837 Organic Chemistry 1.

Summary of Content

The module aims to provide the student with the opportunity to study various elements of organic chemistry, including organometallic compounds, base-catalysed condensation reactions, aromatic heterocyclic compounds, biomolecules and polymers. The programme will include essential mechanistic and stereochemical principles underpinning the chemistry. Nuclear magnetic resonance spectroscopy will be introduced with an emphasis on its application to structural determination

Syllabus

Organometallic and Organophosphrous Compounds Polarity of carbon-metal bonds. Organomagnesium compounds (Grignard reagents); structure, preparation and use in synthesis; comparison with organolithium, organocadmium and organozinc compounds. Phosphorus ylids: preparation and their use in the synthesis of alkenes. Base Catalysed Reactions Acidity of alpha-hydrogens: enolate anions; their generation and role in organic reactions including the aldol condensations; ethylacetoacetate, its preparation and use in the synthesis of ketones and carboxylic acids; diethyl malonate; use in synthesis of carboxylic acids including cycloaliphatic, symmetrical dicarboxylic, alpha, beta-unsaturated acids. Keto-enol tautomerism. Aromatic Heterocyclic Compounds Comparative treatment of structure, properties and reactions of pi - excessive (pyrrole, thiophen and furan) and pi - deficient (pyridine) heterocyclic systems. Stereochemistry Relative stabilities and conformational isomerism of cycloalkanes (C3-C6); cyclohexane, chair/boat/twist forms; relative stabilities; energy profiles; NMR evidence for ring inversion; development to monosubstituted cyclohexanes. Biomolecules Carbohydrates: monosaccharides; glycoside formation; oxidation; reduction; osazone formation; sterochemistry; methylation, disaccharides, polysaccharides, starch, glycogen, cellulose. Aminoacids, peptides and proteins: structure and properties: amino acid sequence in polypeptides and proteins (Sanger and Edman). Primary, secondary and tertiary structure of proteins. Nucleic acids: nucleosides; nucleotides; structure of DNA and RNA and their role in protein synthesis; genetic code; replication process. Lipids classification: chemistry, structure and properties of fatty acids and glyceryl trialkonates. Polymers Types of polymer: addition/condensation: homopolymers and copolymers; thermoplastic/thermosetting. Morphology and crystallinity of polymers; Tg and Tm; factors affecting these parameters including stereochemical (cis-trans isomerism, tacticity), branching, cross-linking, bonding (hydrogen, dipole, Van der Waals). Stereoregulating catalysis (Ziegler-Natta). Step growth and chain growth polymerisation processes: mechanisms and kinetics (free radical, anionic and cationic); chain transfer reactions and effects on polymer properties. Nuclear Magnetic Resonance Spectroscopy Origin of proton magnetic resonance spectra; basic instrumentation; chemical shift; spin-spin coupling; multiplicity, n+1 rule; interpretation of spectra. The syllabus consists of a list of topics normally covered within the module. Each topic may not be dealt with in the same detail.

Learning Outcomes

On successful completion of the module the student should be able to:1. use their knowledge of the properties and reactions of organometallic compounds to devise syntheses of organic compounds;2. apply the general principles of carbon to carbon bond formation by base catalysed condensation reactions to the synthesis of organic compounds;3. analyse by means of models and 3-D drawings, elements of conformational stereochemistry relating to cycloaliphatic compounds;4. apply the principles of aromatic hydrocarbon chemistry to heterocyclic compounds;5. demonstrate a knowledge of the chemical and structural characteristics of biomolecules (proteins, nucleic acids, carbohydrates and lipids) and their role in biochemical systems;6. describe the properties of polymeric materials in terms of their structural characteristics;7. use proton NMR and IR spectroscopic data to determine the structure of organic molecules.

Teaching / Learning Strategy

This module will be taught by an integrated package of lectures reinforced by practical work and tutorials. Students will continue the study of organic chemistry in a way that illustrates it use in the real world in the manufacture of drugs/medicines/pharmaceuticals and the significance of organic pollutants in environmental crime. This is put into a "forensic" context encouraging divergent thinking and broader, deeper learning and leading to an appreciation of the importance of organic chemistry to forensic investigation. Students will take part in practical laboratory work which will further enhance laboratory skills required for further progression and in working as individuals and in groups. The importance of the collation of relevant data, required to make scientific conclusions is emphasised in the way of evidence gathering. Use of state of the art equipment will enhance their employability. Through the use of the managed learning environment GCU Learn, students will become more engaged, flexible and independent in their learning as there will be a wide range of learning resources and basic chemistry search facilities available on line. Students will receive individualised feedback on their performance through one-to-one contact with tutors at tutorials and through the timely return of marked coursework, which will reinforce the students' learning.

Indicative Reading

Organic Chemistry, R. J. Fessenden and J. S. Fessenden, Thomson Learning,, 1998 Organic Chemistry, C. Vollhardt, W H Freeman, 2000 Organic Chemistry, D. C. Hart and L. Hart, Harold, Houghton Mifflin (Academic), 1998 Stereochemistry, D. G. Morris, RSC Publications, 2001

Transferrable Skills

The students will: 1 develop their communication skills, in particular the writing of scientific reports; 2 acquire more advanced laboratory practical skills; 3 augment their interpretative and problem-solving skills by interpreting spectra and deducing the chemical structures which give rise to them.

Module Structure

Activity Total Hours
Assessment (FT) 12.00
Lectures (FT) 24.00
Tutorials (FT) 12.00
Practicals (FT) 18.00
Independent Learning (FT) 134.00

Assessment Methods

Component Duration Weighting Threshold Description
EX1 2.00 60.00 35% Unseen examination, 3 questions from 5.
CW1 n/a 40.00 35% Laboratory Portfolio Learning Outcomes 1,2,3,4,7.