CODE | CHE1360 | ||||||||||||
TITLE | Principles of Organic Chemistry | ||||||||||||
UM LEVEL | 01 - Year 1 in Modular Undergraduate Course | ||||||||||||
MQF LEVEL | 5 | ||||||||||||
ECTS CREDITS | 6 | ||||||||||||
DEPARTMENT | Chemistry | ||||||||||||
DESCRIPTION | Contents: 1. Electronic Theory of Organic Chemistry: Atomic Theory, molecular orbitals and covalent bonding, hybridisation, bonding, conjugation, delocalisation and resonance, homolysis and heterolysis, electron availability in organic molecules, electron density, inductive and mesomeric effects, hyperconjugation, electronic and classical steric effects. 2. Organic Acids and Bases: Factors affecting acidity and basicity including structural and electronic considerations. Effects of delocalisation and electronegativity on the basic nature of molecules containing lone pairs of electrons. 3. Structure and Reactivity: Alkanes and cycloalkanes Functional groups. Structural and physical properties. Naming alkanes and cycloalkanes. Reactions of alkanes, combustion, radical halogenation. Polycyclic alkanes. 4. Stereochemistry: Conventions for drawing 3-D structures, dotted-line/wedge, sawhorse, and Newman conventions, conformations and conformational analysis, staggered, eclipsed and gauche forms, ring systems, chair and boat forms of cyclohexane, axial and equatorial substituents, bond angle strain, transannular interactions, other ring systems, cyclopentane, cyclobutane and cyclopropane. 5. Stereoisomerism: Chiral molecules, asymmetric carbon atoms, enantiomers, chirality in nature, examing a molecule for chirality, optical activity and its detection using plane-polarised light, specific rotation, dextro- and levorotatory molecules, racemates, enantiomeric purity, absolute configuration and the R/S (CIP) sequence rules for nomenclature, Fisher projections and their use and manipulation, diastereomers, tartaric acid, meso compounds, resolution of Enantiomers. Optical activity in molecules possessing no chiral centres: allenes, biphenyls and related structures. Stereochemical aspects of organic reactions: retention, inversion, racemisation. 6. Properties and reactions of haloalkanes: Nucleophilic Substitution Reaction SN1 and SN2 reactions, mechanisms, kinetic evidence; the leaving group, the nucleophile, the substrate; stereochemical implications of mechanism. 7. Further reactions of haloalkanes: Elimination Reactions E1, E2 and E1cB reactions; factors favouring one type of mechanism over the other, stereochemistry of E2 reactions: SYN- and ANTI-elimination; elimination vs substitution. 8. Alkenes, structures and reactivity: Electrophilic additions to C=C Bond Structural and physical properties. Degree of unsaturation. Preparation of alkenes. Catalytic hydrogenation, electrophilic addition of hydrogen halides, water and halogens. E/Z convention for double bond compounds; Anti addition and halonium intermediates, Markownikov's Rule. 9. Free Radical Mechanisms: Factors affecting the stability of free radicals. Formation of free radicals. Reactions: initiation, propagation and termination modes of chain reactions. Important free radical reactions, including allylic bromination by NBS. Aims: To present the basic principles of organic chemistry and introduce the organic reactions of the most common classes of simple organic compounds as detailed in the study-unit description. Learning Outcomes: 1. Classify the organic compounds covered during the study-unit in relation to the functional groups present in the molecule and assign the appropriate name to the organic molecules according to IUPAC rules; 2. Apply electronic and resonance theory in organic chemistry to rationalise the observed stability and reactivity of organic molecules, and be able to use such theory to predict acidity/basicity trends in simple molecules; 3. Draw, name, and manipulate 3-dimensional structures on 2-dimensional media, using all the different standard protocols used by chemists; 4. Illustrate the reactivity and the main reaction mechanisms of the different functionalities discussed; 5. Suggest synthesis of simple organic compounds and apply organic reactions in order to convert simple functional groups. Skills: 1. Management of information to solve problems. Recommended Texts: - Vollhardt, K. Peter C., Schore, Neil E., Organic Chemistry, [[7th ed., 2014] W. H. Freeman & Co. ISBN: 978-1-4641-2027-5. - Sykes P., A Guidebook to Mechanisms in Organic Chemistry, [6th ed., 1986] Longman Publishing Group. ISBN: 0-582-44695-3 - . Mc Murry J., Organic Chemistry. (7th ed., 2008) Thomson Brooks/Cole. - Solomons T.W. G., Fryhle C. B., Snyder S. A., Organic Chemistry (12°Ed.) John Wiley & Sons. |
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STUDY-UNIT TYPE | Lecture | ||||||||||||
METHOD OF ASSESSMENT |
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LECTURER/S | Giovanna Bosica |
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The University makes every effort to ensure that the published Courses Plans, Programmes of Study and Study-Unit information are complete and up-to-date at the time of publication. The University reserves the right to make changes in case errors are detected after publication.
The availability of optional units may be subject to timetabling constraints. Units not attracting a sufficient number of registrations may be withdrawn without notice. It should be noted that all the information in the description above applies to study-units available during the academic year 2024/5. It may be subject to change in subsequent years. |