Module CHEM2087: STRUCTURE AND REACTIVITY IN ORGANIC CHEMISTRY

Department: Chemistry

CHEM2087: STRUCTURE AND REACTIVITY IN ORGANIC CHEMISTRY

Pre-requisites

Corequisites

Excluded Combinations

Aims

• To enhance understanding of the relationship between structure and reactivity (mechanisms) in organic compounds.

Content

• Determination of reaction mechanisms.
• Ring chemistry and stereochemistry.

Learning Outcomes

• draw accurately simple 5 and 6 ring systems and cis and trans-decalins, showing the correct positioning of axial and equatorial groups;
• devise reasonable syntheses of 3 to 9 membered rings, paying attention to strain and stereochemistry of the target molecule including examples of template syntheses;
• devise reasonable mechanisms that account for the reactivity patterns of conformational isomers;
• understand why some cyclisation reactions occur favourably, whereas others ate inhibited, as a result of the requirement for a preferred stereoelectronic pathway;
• use linear free energy relationships to quantify substituent effects and interpret reaction mechanism by analysis of Hammett parameters;
• understand the basis of Hammond’s postulate, kinetic and thermodynamic control and the Curtin-Hammett principle;
• use kinetic data to interpret reaction mechanism by analysis of rate law and the sign or magnitude of the enthalpic and entropic components of the free energy of activation;
• distinguish primary, secondary and solvent kinetic isotope effects and interpret reaction mechanism based on the observed magnitude of these values;
• distinguish between general and specific acid or base catalysis and use the Bronsted linear free energy relationship;
• appreciate solvent effects on pKa and reactivity.

• Group working, encouraged and developed through tutorial teaching.
• Written communication, advanced through the use of essay type questions in lecture-support worksheets.
• Problem-solving, developed through tutorial worksheets.

Modes of Teaching, Learning and Assessment and how these contribute to the learning outcomes of the module

• Lectures are used to convey concepts and are examined by written papers. This is the best method to assess the knowledge of the students.
• Tutorials are given to ensure that the students have grasped the concepts given in the lectures and to practice examples of problems. The work is formatively assessed.
• Workshops are larger groups of students where problems are considered and common difficulties shared. This ensures that students have understood the work and can apply it to real life situations. These are formatively assessed.

Teaching Methods and Learning Hours

Summative Assessment

Formative Assessment

Set work in preparation for tutorials and workshops.