Synthesis and Mechanisms of Organic Reactions

Recommended Prerequisites

Orgânic Chemistry I,  Orgânic Chemistry I I 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

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

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

Ability to solve problems in Organic Chemistry Learn to substantiate arguments when making decisions

 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

 Have skills which enable self-learning throughout life.

Work Placement(s)

No

Syllabus

Mechanisms of Organic Reaction: Thermodynamic and Kinetic requirements of a reactio
Reactive intermediate
Rearrangements
Stereoelectrónic Effect
Hard and Soft Acids and Bases

Isotopic labeling and Isotope effects
Chirality and 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 Material
Building Blocks for Polyethylene, Polypropylen

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

1. Pinho e Melo, "Mecanismos de Reacções Orgânicas", LIDEL-Edições Técnicas, 2005
2. Barry K. Carpenter, “Determination of Organic Reaction Mechanisms”, John Wiley & Sons, 1984
3. Jerry March, “Advanced Organic Chemistry”,  John Wiley & Sons, 1985
4. Laurence M. Harwood, “Polar Rearrangements”, Oxford Science Publications, 1992
5. A. J. Kirby, “Stereoelectronic Effects”, Oxford Science Publications, 1996
6. Christopher J. Moody e Gordon H. Whitham, “Reactive Intermediates”, Oxford Science Publications, 1992
7. “Reactive Intermediate Chemistry”, Ed. R. A. Moss, M. S. Platz and M. Jones Jr., John Wiley & Sons, 2004
8. Clayden, Greeves, Warren, Wothers, “Organic Chemistry”, Oxford University, 2001
9. R. Bruckner, “Advanced Organic Chemistry”, Ed. A. Harcourt Science and Technology Company, 1996
10. “Organic Chemistry , Principles and Industrial Practice”, Wiley-VCH, 2003, Mark M. Green, Harold A. Wittcoff
11. “Industrial Organic Chemistry”, Wiley-VCH, 2008, K. Weissermel, H.-J. Arper