Ateneo - UPO

Chemistry of the most important classes of I and II metabolites
Non-ionic reaction mechanisms (pericyclic reactions, reactions mediated by transition metals, radical reactions)
Introduction to proces development. protecting groups

Clayden, J et al.. Organic Chemistry, Oxford University Press, 2012.
Norman, Coxon. Sintesi Organica, Piccin, 1999.
Farina, V. Dispense sul corso di chimica organometallica AA 2001-2002

Provide students with instruments to critically tackle complex molecules and reaction mechanisms.

General and inorganic chemistry
Organic chemistry II
Heterocyclic chemistry

Lessons and problem-solving sessions involving the students
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/services-students-physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

Supporting material to the course will be added to the DIR platform.
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/services- students physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects

the exam will be divided into two parts. First part (5 points) is the presentation of a project relating to an organic chemistry topic chosen by the students.
Written exam (25 points)

1. Reactions mediated by transition metals
1. 18-electrons rule, classification of ligands and nature of the coordinative bond
2. General mechanistic considerations
3. Hydroformylation and metathesis
4. Coupling reactions and Heck reaction
5. Exercises and problem-solving activities
6. Exercises and problem-solving activities
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

2.Pericyclic reactions
1. Introduction and selection rules
2. Cycloaddition reactions and structure-reactivity relationships in dienic synthesis
3. Dipolar cycloadditions
4. Electrocyclic reactions
5. Sigmatropic reactions
6. Application to industrial syntheses (vitamin D, citral)
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

3.Carbohydrates
1. Representation and semiacetal formation
2. Anomeric effect and introduction to hyperconjugation
3. Protection reactions
4. Glycosidation reactions
5. Redox reactions
6. Application to industrial syntheses (Reichstein synthesis of vitamin C)
7. Solid-phase oligonucleotide synthesis
8. Exercises and problem-solving activities

4. Amino acids and peptides
1. Acid-basic properties of proteinogenic amino acids and their general synthesis
2. Asymmetric synthesis of amino acids
3. Solution peptide synthesis
4. Solid state peptide synthesis and introduction to polymer chemistry
5. Polymerization reactions
6. Application to industrial syntheses (Monsanto synthesis of L-DOPA)
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

5. Secondary metabolites
1. Isoprenoids and non-classic carbocations
2. Application to industrial syntheses (carotenoids)
3. Application to industrial syntheses (steroid syntheses)
4. Alkaloids
5. Multicomponent reactions (Mannich, Ugi, Passerini)Aymmetric dihydroxylation
7. Quinones
8. Exercises and problem-solving activities

6a. Stereoelectronic effects
1. General introduction
2. Application to conformational effects
3. Application to configurational effects
4. Exercises and problem-solving activities

6b. Organic photochemistry
1. General aspects
2. Synthetic uses
3. Photocycloadditions and their biological relevance
4. Exercises and problem-solving activities

7. Biological mechanisms
1. Benzoinic reaction and vitamin B1
2. Vitamin K
3. Electron-transfer reactions
4. Diotopic reactions and vitamin B12
5. Redox reactions and half-bonds
6. Exercises and problem-solving activities
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

8. protecting groups of the main functional groups

Capacity to address the chemistry and the synthesis of complex molecules applying modern reaction mechanisms