Learning objectives
At the end of the course the student is expected to be able to:
1. KNOWLEDGE AND UNDERSTANDING.
1a. To recognize the main functional groups within complex molecules.
1b. To recognize nomenclature, structure and reactivity of the main classes of organic compounds, be they linear, cyclic, heterocyclic, or fused bicycles.
1c. To explain and appropriately exemplify the principles that guide the main organic reactions and allow the rational interpretation of reaction mechanisms.
2. APPLIED KNOWLEDGE AND UNDERSTANDING.
2a. To implement the theoretical knowledge acquired to solve simple problems.
2b. To predict the outcome of chemical transformations.
2c. To critically address the design of a credible synthetic plan to access simple molecules.
3. COMMUNICATION AND LEARNING SKILLS.
3a. To communicate in a clear way and with appropriate technical language conclusions and knowledge to specialist and non-specialist interlocutors, in accordance with the training objectives described above.
4. MAKING JUDGEMENTS.
4a. To evaluate in a critical way a synthetic strategy aimed at obtaining a polyfunctionalized molecule of small dimensions.
Prerequisites
Organic Chemistry II (COII) course involves the successful acquisition of all the topics covered in the Organic Chemistry I (COI) course.
1. Molecular electronic configuration: atomic orbitals, molecular orbitals and hybrid orbitals.
2. Structure and hybridization of carbon chains.
3. Conformational and configurational analysis of carbon chains.
4. Acid-base equilibria.
5. Nucleophiles and electrophiles.
6. Main classes of chemical reactions: addition, substitution, redox.
7. Structure and nomenclature of the main classes of functional groups treated during Organic Chemistry I.
8. Inductive effects and resonance effects.
Please note the following:
1. in order to take the COII EXAM, it is MANDATORY to have passed the COI exam;
2. it is NOT REQUIRED to have passed the COI exam to attend the COII course
3. in order to fully UNDERSTAND the COII , it is RECOMMENDED to have studied the COI topics.
Those who want to attend COII without ever having studied COI topics are asked to get in touch with the professor BEFORE classes begin.
Course unit content
This course will cover general topics concerning the reactivity and structure of the major classes of organic compounds not covered in Organic Chemistry I. The course will be divided into three main Chapters:
1. The chemistry of aromatic systems
2. The chemistry of enols and enolate anions
3. Pericyclic reactions
Special emphasis will be given to those issues related to the formation of new carbon-carbon bonds and the formation and manipulation of functional groups.
Full programme
1. CARBANION REACTIVITY (2.75 CFU)
1a. Carbanions: structure, synthesis and reactivity
1b. Enols and enolates; keto-enolic tautomer; acidity and basicity of enolizable compounds.
1c. Enolization catalyzed by acids and bases; metal enolates; ammonium enolates; silicon stabilized enolates; kinetic enolates vs. thermodynamic enolates; control of the Z/E geometry of an enolate; non-carbonylic enolates; ilids.
1d. Halogenation and nitrosation of enolates
1e. Alkylation of enolates and enamines: malonic synthesis and inter- and intramolecular Michael reaction.
1f. The aldol reaction: the "classical" acidic and base-catalyzed aldol reaction; the cross aldol reaction; Mukaiyama variant; intramolecular aldol reaction; Henry's reaction; Knovenagel's reaction.
1g. Mannich reaction: imine and imminium ions; direct and indirect Mannich reaction; Pictet-Spengler reaction.
1h. Claisen and Dieckmann Reactions; acetoacetic synthesis.
1i. Domino reactions: Bayliss-Hillman reaction; Robinson annulation.
2. PRINCIPLE OF VINYLOGY (0.25 CFU)
2a. Definitions
2b. Vinylogous Aldol, Mannich, ad Michael reactions.
3. OLEFINATION REACTIONS (0.25 CFU)
3a. Stabilized and non-stabilized phosphorus ylides.
3b. Wittig reaction; Horner-Hemmons and its variants; Still-Gennari reaction.
3c. Sulfur ylides and Julia olefination.
4. CARBOCATION REACTIVITY (0.5 CFU)
4a. Carbocations: basic structure, synthesis and reactivity.
4b. Pinacolic and semi-pinacolic rearrangement; ring expansion and contraction; Wagner-Meerwein rearrangement; Grob fragmentation.
4c. Prins reaction.
5. AROMATIC COMPOUNDS (2 CFU)
5a. Aromaticity and nomenclature of aromatic compounds
5b. Reactivity of Benzene and its derivatives
5c. Electrophilic Aromatic Substitution (EAS)
5d. Diazonium salts
5e. Synthesis of mono- and multi-substituted benzene derivatives
5f. Nucleophilic Aromatic Substitution; Benzyne.
6. INTRODUCTION TO PALLADIUM CHEMISTRY (1 CFU)
6a. Transition metals
6b. Introduztion to the reactivity of Palladium complexes
6c. Palladium-catalyzed cross couplings: Heck, Suzuki, Stille, Sonogashira.
7. PERICYCLIC REACTIONS (1.0 CFU)
7a. Classification of pericyclic reactions.
7b. Woodward-Hoffmann Rules
7c. Diels-Alder Reaction
7d. Sigmatropic transpositions.
8. PRINCIPLES OF CHEMICAL SYNTHESIS (0.25 CFU)
8a. Introduction to chemical synthesis: divergent vs convergent synthesis
8b. Protecting groups
8c. Applications to the total synthesis of drugs
Bibliography
Suggested textbook:
J. CLAYDEN, N. GREEVES, S. WARREN, "Organic Chemistry", Second edition, Oxford 2012.
Supplementary material:
Scientific articles suggested by the teacher
Reference books:
1. Kurti Laslo, Czako Barbara "STRATEGIC APPLICATIONS OF NAMED REACTIONS IN ORGANIC SYNTHESYS", Academic Press, 2005.
2. Francis A. Carey, Richard J. Sundberg "Advanced Organic Chemistry. Part A: Structure and Mechanisms", Springer-Verlag; Fifth Ed. 2007.
3. Francis A. Carey, Richard J. Sundberg "Advanced Organic Chemistry. Part B: Reaction and Synthesis", Springer-Verlag; Fifth Ed. 2007.
Teaching methods
The lessons will be held "in presence" and in accordance with the guidelines of the CTF Course, attendance is mandatory. In case of emergency period restrictions the lessons will be provided by "distance learning" in synchronous (direct) mode, through the use of the Teams and Elly platforms.
During the lessons, moments of frontal teaching will alternate with interactive moments with the students. To promote active participation several activities will be proposed through the use of some digital resources such as Elly Discussion Forums or practice tests through the Office 365 Forms application.
The didactic activities will be conducted by privileging modalities of active learning alternated to heuristic Socratic lessons. During the heuristic-socratic lessons will be privileged the dialogical confrontation with the classroom, on the theoretical aspects of the topics of the course, in order to bring out any pre-knowledge on the topics in question by the trainees. In the second part of the lesson will be activated cycles of experiential learning in which students will be required to apply the theoretical concepts learned to the resolution of appropriate written exercises. In addition, "case studies" taken from the scientific literature (empirical research projects) will be analyzed and the students will have to critically analyze them according to the methodological criteria illustrated in the lessons and in the bibliographic and didactic material.
The slides used to support the lessons will be uploaded weekly on the Elly platform. In order to download the slides it is necessary to register for the online course. The slides are considered an integral part of the teaching material. Non-attending students are reminded to check the available didactic material and the indications provided by the teacher through the Elly platform.
The recordings of the lessons and the links to the Forms exercises will be available to the students on the Elly platform: the presence of this material does not exempt the student from the mandatory "in presence" attendance of the course.
Assessment methods and criteria
The assessment of achievement of the course objectives involves a written test follow by an oral test.
In order to be admitted to the written test, students must register through the ESSE3 platform for the roll called PARTIAL TEST.
In order to be eligible for the oral test, students must compulsorily register for the appeal called APPEAL WITH ONLINE VERBALIZATION.
The written test involves solving a series of exercises (3 to 5) on the course topics, interspersed with theory and nomenclature questions. Having passed the written test with a grade of not less than 18/30, the student will be eligible for the oral test.
The oral test involves the discussion of a written report on a total synthesis. All students who have correctly submitted the "homework" assigned while attending the course are exempt from the written report.
The oral test will focus on questions regarding the course content and will be structured in open-ended questions, generally concerning the theoretical aspects of the course, and exercises aimed at verifying that the student is able to correctly apply the theoretical concepts to the recognition and synthesis of polyfunctionalized small organic molecules. In addition, it will be assessed that the student is able to communicate processes and outcomes using discipline-specific terminology. The written report, to be completed if the "homework" assigned during the course has not been uploaded, involves the study and critical commentary of a published total synthesis as well as the key mechanisms and transition states covered by the assigned synthesis. The work is to be handed in to the lecturer in hard copy no later than two weeks before the date of the call in which you intend to take the oral test. More information regarding completion and verification will be given during the course and full instructions will be uploaded to the Course Elly platform.
The written test is graded on a 0-30 scale and will have a weight on the final grade of 70%.
The oral test is graded on a 0-30 scale and will have a weight on the final grade of 30%.
If the presentation of the paper is not due, the evaluation will be on the oral test only.
The final grade, which is defined non-analytically but subjectively by the lecturer, will be announced immediately upon completion of the oral test. Please note that online registration for the roll call is MANDATORY.
Other information
During the course, "assignments" will be given, which the student will be required to "hand in" (upload) by a deadline (generally 1 week) on the Elly platform. Carrying out the assignments (generally exercises related to the course content) is not mandatory, but it will avoid the compilation of the written report and its subsequent discussion during the exam.
2030 agenda goals for sustainable development
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