Synthesis and Mechanisms of Organic Reactions

Recommended Prerequisites

Organic Chemistry I,  Organic Chemistry II and Chemical Synthesis.

Teaching Methods

The teacher should present topics with updated information based on his experience as a researcher. Some scientific studies developed by the teacher can be discussed when they fall in the syllabus content.

Some mechanistic problems will be presented and their resolution should be done with an oral discussion as well as with the submission of a written report. In this way the student will be followed more closely. A theme within the subject content of the curricular unit will also be presented on which the student must submit a written review.

Learning Outcomes

Knowledge and ability to understand

Recognize and apply basic concepts and principles in Organic Chemistry allowing the interpretation of Synthetic Processes and Mechanisms of Organic Reactions.

Ability to analyze, synthesize and understand.

 

Applying knowledge and understanding

Learn to apply acquired knowledge in the individual´s vocational area at the professional approach level.

 

Judgment / decision making

Ability to solve problems in Organic Chemistry.

Learn to substantiate arguments when making decisions

 

Communication

Understand and know how to use information sources. Ability to search and use bibliography

Acquire skills for communicating information clearly, with speech and other appropriate means. Acquire skills in structured presentations of scientific matters to a competent audience, ability to debate, whether orally or in writing.

 

Skills related to self-learning

Have skills which enable self-learning throughout life.

Work Placement(s)

No

Syllabus

Mechanisms of Organic Reaction: Thermodynamic and Kinetic requirements of a reaction

Reactive intermediates

Rearrangements

Stereoelectrónic Effects

Hard and Soft Acids and Bases

Isotopic labeling / Isotope effects

Chirality / Stereochemistry

Direct detection of intermediates. IR with Matrix isolation Methods. NMR of carbocations in superacid medium. ESR and CIDNP. Characterization of carbocations by X-ray diffraction. Stabilization of reactive intermediates in Molecular Cages (Molecular encapsulation). Methods of high temporal resolution

Industrial Synthesis

The Importance of Petrochemicals in Industry

Conversion of Petroleum to Useful Materials

Building Blocks for Polyethylene, Polypropylene

Electrophilic Aromatic Substitution in Industrial Synthesis

Building Blocks for Polystyrene, Polycarbonate and epoxy resin

Chirality and Biological Activity in Industry

Resolution, the chiral pool, asymmetric synthesis

Top 10 commercial chiral pharmaceuticals: Examples of Industrial synthesis

Head Lecturer(s)

Teresa Margarida Vasconcelos Dias de Pinho e Melo

Assessment Methods

Assessment
Project: 25.0%
Exam: 75.0%

Bibliography

Teresa M. V. D. Pinho e Melo, "Mecanismos de Reacções Orgânicas", LIDEL-Edições Técnicas, Colecção Química–SPQ, 2005

Barry K. Carpenter, “Determination of Organic Reaction Mechanisms”, John Wiley & Sons, 1984

Jerry March, “Advanced Organic Chemistry”,  John Wiley & Sons, 1985

 Laurence M. Harwood, “Polar Rearrangements”, Oxford Science Publications, 1992

A. J. Kirby, “Stereoelectronic Effects”, Oxford Science Publications, 1996

Christopher J. Moody e Gordon H. Whitham, “Reactive Intermediates”, Oxford Science Publications, 1992

“Reactive Intermediate Chemistry”, Ed. R. A. Moss, M. S. Platz and M. Jones Jr., John Wiley & Sons, 2004

Clayden, Greeves, Warren, Wothers, “Organic Chemistry”, Oxford University, 2001

R. Bruckner, “Advanced Organic Chemistry”, Ed. A. Harcourt Science and Technology Company, 1996

“Organic Chemistry , Principles and Industrial Practice”, Wiley-VCH, 2003, Mark M. Green, Harold A. Wittcoff

“Industrial Organic Chemistry”, Wiley-VCH, 2008, K. Weissermel, H.-J. Arper