Organic Chemistry III

The targets of the course are:

1. Focus on some important aspects of Organic Chemistry (such as aminoacids, catalysis, pericyclic reactions, organometallic reactions, retrosynthesis), with particular attention to the mechanistic point of view and to the Physical Organic Chemistry
2. Analyze some important organic reactions, focusing the reaction mechanism
3. Develop the ability to design and realize new synthetic pathway to obtain new organic molecules
4. Study the main non-covalent interactions and their application in the modern Synthetic Organic Chemistry

Regarding the Dublin Descriptors, this course aims to transfer the following transversal competences to the student:
Knowledge and understanding:
 Inductive and deductive reasoning skills;
 Ability to rationalize and predict the reactivity of organic molecules;
 Ability to distinguish the difference between covalent and non-covalent interactions;
 Ability to predict the kinetic course of a reaction.
 
Ability to apply knowledge:
 Ability to design a synthetic path suitable for obtaining a precise organic molecule;
 Ability to predict the course of a reaction based on precise experimental parameters;
 Ability to identify the conditions for optimal reactions for a synthetic strategy.
 
Autonomy of judgment:
 Critical reasoning skills;
 Self-assessment of learning through interactions in the classroom with colleagues and with the teacher.

Communication skills:
 Ability to describe in oral and written form, with properties of language and terminological rigor, one of the topics covered, making use of both power point presentations and the blackboard.

Lessons will be carried out in classroom, with the use of power point presentations and the use of the blackboard.

Periodically, some meeting will be done, also by using informatics platforms, to check the level of learning and to clarify some arguments.

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus.

Learning assessment may also be carried out on line, should the conditions require it.

 

• AMINOACIDS AND PROTEINS
  • aminoacids, acid-base properties, peptides, polypeptides and proteins, structure of proteins, synthesis of polypeptides
• PERICYCLIC REACTIONS 
  • Conjugated dienes, molecular orbitals and symmetry, Dies-Alder reactions, electrocyclic reactions, sigmatropic reactions, pericyclic reactions, synhtesis and structure of bicycloalkanes.
• CATALYSIS
  • Genelar aspects and energetics, Proximity effect and orientation, Type of catalysis (electrophilic, metallic, acid-base, nucleophilic), General and specific catalysis, Intramolecular catalysis. 
  • Enzymatic catalysis: general considerations, enzymes classification, Some important enzymatic catalysis mechanisms. Cynetics into enzymatic catalysis, Michaelis-Menten equation.
  • Enzymati inhibitors: reversible competitive inhibition, reversible non-competitive inhibition, reversible acompetitive inhibition, irreversible inhibition.
  • Artificial enzymes.
• ORGANOMETALLIC COMPOUNDS AND FORMATION OF NEW C-C BONDS
  • the chemical bond in the organometallic compounds, organolitium compounds and Grignard reagents.
  • Reactivity: coupling reactions, Gilman reagents, Heck reaction, Stille reaction, Suzuki reaction, Sonogashira reaction, Negishi reaction
  • Metathesis reactions: Ring Opening Metathesis Polymerization (ROMP), Ring Closing Metathesis (RCM), Acyclic Diene Metathesis polymerization (ADMET), CM (Cross Metathesis)
  • Click chemistry: 1,4 and 1,5 cycloaddition reactions 
• RETROSYNTHESIS
  • Organic synthesis strategiee: retrosynthesis and disconnection approach
  • Decaroxylation of b-ketoacids, reaction with diazomethane, Williamson synthesis, allenes synthesis, ethers synhtesis, ester and amide synthesis by carbodiimides
  • Alkenes reactions: Wittig reaction and Horner-Wadsworth-Emmons reaction
  • Oxygen transfer reactions: alkenes oxidation, reaction with OsO4, O3, synhtesis and reaction of epoxides, Pinacolyc rearrangment, Bayer-Williger reaction, Wolf-Kishner reaction
  • Strategies of FGI, activating and deactivating groups, protective groups
  • Examples of disconnections
• NON COVALENT INTERACTIONS
  • ion pairing. electrostatic interactions, hydrogen bond, pi-interactions, hydrophobic effect, aggregation of organic compounds in water

1. Chimica Organica 5e Edises Brown,Foote, Anslyn
2. P. Y. BRUICE - Chimica organica - 2a Edizione EdiSES
3. Warren, Wyatt- Organic Synthesis: the Disconnection approach 2 ed. Wiley 2011
4. Materiale didattico fornito dal docente

The exam will be taken orally. The exam topics will be strictly related to those developed during the lessons.

The objective of the exam will be to evaluate:

the achievement of the objectives of the course and in particular:

the ability to design a synthesis using the retrosynthetic approach

the understanding of the reaction mechanisms analyzed during the lessons, proposing plausible mechanisms also for new reactions

understanding of the different types of catalysis

understanding the differences between the various types of non-covalent interactions

Verification of learning can also be carried out electronically, should the conditions require it.

Disconnection of an organic molecule

Optimization of the synthesis process

Definition of catalysis

Thermodynamic principles governing host-guest interactions

Electrocyclic reactions