Organic Chemistry III
Academic Year 2023/2024 - Teacher: GIUSEPPE TRUSSO SFRAZZETTOExpected Learning Outcomes
The targets of the course are:
- 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
- Analyze some important organic reactions, focusing the reaction mechanism
- Develop the ability to design and realize new synthetic pathway to obtain new organic molecules
- 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.
Course Structure
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.
Required Prerequisites
Attendance of Lessons
Detailed Course Content
- 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
Textbook Information
- Chimica Organica 5e Edises Brown,Foote, Anslyn
- P. Y. BRUICE - Chimica organica - 2a Edizione EdiSES
- Warren, Wyatt- Organic Synthesis: the Disconnection approach 2 ed. Wiley 2011
- Materiale didattico fornito dal docente
Course Planning
Subjects | Text References | |
---|---|---|
1 | Amminoacidi, proprietà chimiche | Brown, appunti di lezione |
2 | Peptidi, polipeptidi e proteine | Brown, appunti di lezione |
3 | Sintesi di polipeptidi | Brown, appunti di lezione |
4 | Struttura primaria, secondaria e terziaria dei polipeptidi e delle proteine | Brown, appunti di lezione |
5 | Struttura tridimensionale delle proteine | Brown, appunti di lezione |
6 | Reazioni elettrocicliche | Brown, appunti di lezione |
7 | Reazioni di cicloaddizione | Brown, appunti di lezione |
8 | Trasposizioni sigmatropiche | Brown, appunti di lezione |
9 | Catalisi: Aspetti generali ed aspetti energetici. | Bruice, appunti di lezione |
10 | Catalisi Enzimatica | Bruice, appunti di lezione |
11 | Inibitori enzimatici | Bruice, appunti di lezione |
12 | Enzimi artificiali | Appunti di lezione |
13 | Composti organometallici | Bruice, appunti di lezione |
14 | Reattività dei composti di organometallici | Bruice, appunti di lezione |
15 | Reazioni di metatesi | Appunti di lezione |
16 | Click Chemistry | Appunti di lezione |
17 | Strategie di sintesi organica: retrosintesi e disconnessioni. | Warren, appunti di lezione |
18 | Decarbossilazione di -chetoacidi. Formazione di esteri metilici mediante diazometano, Sintesi di Williamson degli eteri, Sintesi di alleni. Sintesi di eteri. | Brown, appunti di lezione |
19 | Sintesi di alcheni: reazione di Wittig, Reazione di Horner-Wadsworth-Emmons | Bruice, appunti di lezione |
20 | Reazioni di trasferimento di ossigeno | Bruice, appunti di lezione |
21 | Reazioni di ossidoriduzione | Bruice, appunti di lezione |
22 | Interazioni non-covalenti | Appunti di lezione |
23 | Macrocicli abiotici | Appunti di lezione |
24 | Principi termodinamici delle interazioni Host-Guest | Appunti di lezione |
Learning Assessment
Learning Assessment Procedures
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.
Examples of frequently asked questions and / or exercises
Disconnection of an organic molecule
Optimization of the synthesis process
Definition of catalysis
Thermodynamic principles governing host-guest interactions
Electrocyclic reactions