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Module Code - Title:

CH4008 - ORGANIC PHARMACEUTICAL CHEMISTRY 2

Year Last Offered:

2021/2

Hours Per Week:

Lecture

2

Lab

0

Tutorial

1

Other

2

Private

5

Credits

6

Grading Type:

N

Prerequisite Modules:

CH4008

Rationale and Purpose of the Module:

To build on the functional group chemistry covered in CH4102, CH4103, CH4104 and CH4007. To extend the studentsÆ comprehension and working knowledge of functional group chemistry; to expand the range of reagents, reactions and associated mechanisms; to detail how structure and reactivity can be quantitatively correlated; to detail quantitative aspects of acid and base catalysis.

Syllabus:

Section A: Regiochemical control: addition of HBr by ionic and radical mechanisms, alcohol formation by acid catalysed hydration and via hydroboration; Chemoselective control: Lindlars catalyst and dissolving metal reduction; hydride reducing reagents, Reformatsky reaction; use of protecting groups. Stereochemical control: asymmetric induction, diastereomeric selectivity, Felkin-Anh model; enantiomeric selectivity, chiral hydride reagents (Alpine Borane and Alpine Borohyrdides), chiral catalysts -Monsanto catalyst for L-Dopa production. Section B: Quantitative structure activity relationships: development and use of the Hammett equation; definition of general and specific acid and base catalysis, use of buffers and kinetic data to distinguish between general and specific catalysis, quantitative analysis of data. Named (and other) Reactions: Oral presentation by students on reactions such as Hydroboration, Reformatsky, Dihydroxylation, Mannich Reaction, Reductive Amination, Birch Reduction, Michael Addition, Allylic bromination, Sharpless Epoxidation, Mitsunobu Reaction, Suzuki Coupling, Heck Reaction, Benzyne chemistry.

Learning Outcomes:

Cognitive (Knowledge, Understanding, Application, Analysis, Evaluation, Synthesis)

Evaluate a linked set of synthetic reactions, associate the required reagents and assess region-, chemo- and stereochemical aspects where relevant.Explain, rationalize and illustrate with a relevant example, how diastereo- and enantioselectivity can be achieved.Describe how a pattern of reactivity can be quantitatively related to structural parameters using the Hammett equation.Calculate a Hammett r value from kinetic (or equilibrium) data and interpret its sign and magnitude in terms of a reaction mechanism.Explain how general acid/base catalysis differs from specific acid/base catalysis.Show how kinetic data obtained in buffers can be used experimentally to distinguish general from specific acid/base catalysisDerive the kinetic equations for specific acid and specific base catalysed reactions.Determine values for rate constants and for equilibrium constants from sets of kinetic data.

Affective (Attitudes and Values)

Demonstrate an appreciation of the role of organic chemistry as a fundamental molecular science.

Psychomotor (Physical Skills)

N/A

How the Module will be Taught and what will be the Learning Experiences of the Students:

This module will be taught over a 12 week period through a formal interactive lecturing mode (2 x 1 hour lectures; 1 hour tutorial per week). Student presentations (20 minutes) will from weeks 5-11) and a synoptic oral (25 minutes) will take place in week 12. The module will be assessed by an end-of-semester written exam (75% of final marks); student oral presentation (15%); student synoptic oral (10%).

Research Findings Incorporated in to the Syllabus (If Relevant):

Prime Texts:

J. Clayden, N. Greeves, N. Warren and P. Wothers (2001) Organic Chemistry , Oxford University Press
J. March (1992) Advanced Organic Chemistry , Wiley
Neil S. Isaacs (1998) Physical Organic Chemistry , Longmans

Other Relevant Texts:

Programme(s) in which this Module is Offered:

Semester - Year to be First Offered:

Spring - 09/10

Module Leader:

Peter.Davern@ul.ie