Study-Unit Description

CODE

CHE1360

TITLE

Principles of Organic Chemistry

UM LEVEL

01 - Year 1 in Modular Undergraduate Course

MQF LEVEL

ECTS CREDITS

DEPARTMENT

Chemistry

DESCRIPTION

Contents:

Section A:

  1. Electronic Theory of Organic Chemistry:
      Atomic Theory, 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. Stereochemistry:
      Conventions for drawing 3-D structures, dotted-line/wedge, sawhorse, and Newman conventions, rotamers and
      potential-energy diagrams, 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.

  4. 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 - chemical and physical methods.

  5. Stereochemical aspects of organic reactions:
      Retention, inversion, racemisation, enantiotopic and diastereotopic atoms and faces, asymmetric synthesis.

  6. Optical activity in molecules possessing no chiral centres:
      Allenes, biphenyls and related structures.

Section B:

  1. Nucleophilic Substitution Reaction:
      SN1 and SN2 reactions: Kinetic evidence; stereochemical implications of mechanism: Walden inversion; SNi and
      retention of configuration.

  2. 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.

  3. Electrophilic and Nucleophilic Addition to C=C Bond:
      E/Z convention for double bond compounds; Anti addition and halonium intermediates, Markownikov's Rule and
      the peroxide effect, hydroboration; addition to conjugated dienes: Diels Alder reaction (pericyclic mechanism).
      Nucleophilic addition: Michael reaction; 1,4-addition to αß - unsaturated carbonyl groups.

  4. Nucleophilic Addition to C=O Bonds:
      Electronic and steric effects and acid/base catalysis of carbonyl addition reactions. Hemi-acetal, acetal and ketal
      formation and other additions including those involving metallohydrides and alkoxides; Cannizzaro reaction,
      pinacol formation and rearrangement; condensation reactions of aldehydes and carboxylic derivatives; addition
      of carbanions, including aldol type reactions: Claisen-Schmidt, Perkin etc., benzoin condensation.

  5. 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.

Recommended Texts:

  - Vollhardt, K. Peter C., Schore, Neil E., Organic Chemistry, [5th ed., 2007] W.H. Freeman & Co. ISBN: 7167-9949-9
  - Sykes P., A Guidebook to Mechanisms in Organic Chemistry, [6th ed., 1986] Longman Publishing Group.
      ISBN: 0-582-44695-3
  - Edenborough M., Writing Organic Reaction Mechanisms. A practical guide, Taylor and Francis, 1994.
      ISBN: 0-7484-0171-7

STUDY-UNIT TYPE

Lecture

METHOD OF ASSESSMENT

Assessment Component/s	Assessment Due	Sept. Asst Session	Weighting
Progress Test	SEM2	No	15%
Examination (3 Hours)	SEM2	Yes	85%

LECTURER/S

Giovanna Bosica

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 2023/4. It may be subject to change in subsequent years.

Study-Unit Description

Study-Unit Description

Study at UM