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 complex 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, in particular:
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. Inductive effects and resonance effects.
7. Main classes of chemical reactions: addition, substitution, redox.
8. Structure and nomenclature of the main classes of functional groups treated during Organic Chemistry I.
9. General reactivity of the main classes of functional groups treated during Organic Chemistry I.
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 contents, it is RECOMMENDED to have studied the COI topics.
Those willing to attend the COII course without ever having studied the COI contents are asked to get in touch with the lecturer BEFORE the course 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 course. 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 with an introduction to organic synthesis.
Full programme
1. CARBOCATION REACTIVITY (1.0 CFU)
1a. Carbocations: basic structure, formation and reactivity.
1b. Pinacolic and semi-pinacolic rearrangement; ring expansion and contraction; Wagner-Meerwein rearrangement.
1c. Prins reaction.
2. AROMATIC COMPOUNDS (2 CFU)
2a. Aromaticity and nomenclature of aromatic compounds.
2b. Reactivity of benzene and its derivatives.
2c. Aromatic electrophilic substitution.
2d. Diazonium salts.
2e. Synthesis of mono- and multi-substituted benzenes.
2f. Aromatic nucleophilic substitution.
2g. Introduction to benzynes.
3. INTRODUCTION TO PALLADIUM CHEMISTRY (0.5 CFU)
3a. Electronic and orbital systems of transition metals.
3b. Basic reactivity of palladium and its complexes.
3c. Palladium-catalysed carbon-carbon bond formation: Heck, Suzuki, Stille, Sonogashira.
4. REACTIVITY OF CARBANIONS (3.00 CFU)
4a. Carbanions: structure, formation and properties
4b. Enols and enolates; keto-enol tautomeria; acidity and basicity of enolizable compounds.
4c. Acid- and base-catalyzed enolization; metal enolates; ammonium enolates; silicon-stabilized enolates; kinetic vs. thermodynamic enolates; noncarbonyl enolates; ilides.
4d. Halogenation of enolates; haloform reaction.
4e. Alkylation of enolates and enamines: malonic synthesis; inter- and intramolecular Michael reaction
4f. The aldolic reaction: the "classical" acid- and base-catalyzed aldolic reaction; the cross aldolic reaction; Mukaiyama variant; intramolecular aldolic reaction; vinyloga aldolic reaction. Henry's reaction. Knovenagel's reaction.
4g. Mannich reaction: imines and iminium ions; direct and indirect Mannich reaction; vinyloga Mannich reaction.
4h. Claisen and Dieckmann reactions; acetoacetic synthesis.
4i. Cascade reactions: Bayliss-Hillman reaction; Robinson anellation.
5. OLEFINATION REACTIONS (0.25 CFU).
5a. Stabilized and unstabilized phosphorus ylides.
5b. Wittig reaction; Horner-Hemmons and its variants; Still-Gennari reaction.
5c. Sulfur ylides and Julia olefination.
6. PERICYCLIC REACTIONS (1 CFU)
6a. Classification of pericyclic reactions.
6b. Woodward-Hoffmann rules.
6c. Diels-Alder reaction
6d. Sigmatropic transpositions.
7. PRINCIPLES OF CHEMICAL SYNTHESIS (0.25 CFU)
7a. Introduction to chemical synthesis: divergent vs convergent syntheses; retrosynthetic approach.
7b. Protective groups.
7c. Case studies.
Bibliography
Suggested textbook in addition to that provided for organic chemistry I course:
J. CLAYDEN, N. GREEVES, S. WARREN, "Organic Chemistry", Second edition, Oxford 2012.
Supplementary material:
Scientific articles suggested by the lecturer and made available on the Elly platform.
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 to the
online course. The slides are considered an integral part of the teaching material and DO NOT REPLACE the textbook. Non-attending students are reminded to check the available material and the indications provided by the teacher through the Elly platform.
All lessons will be recorded and made available to students on the Elly platform for a period not exceeding 15 days.
Teaching methods
The lessons will be held "in presence" and in accordance with the guidelines of the CTF Course, ATTENDANCE IS MANDATORY.
Lessons will include moments of frontal teaching alternated 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" and "HOMEWORK". Documented participation and execution of the homeworks proposed by the lecturer during thelessons (not less than 90%), carries a "bonus" in the examination (i.e., a written report on a total synthesis will be EXEMPTED).
The activities will be conducted with active learning modalities favoring the dialog with the students. Appropriate written exercises will be proposed. In addition, "case studies" taken from the scientific literature (empirical research projects) will be analyzed with the students according to the methodological criteria illustrated in the lessons and in the bibliographic and didactic material.
Assessment methods and criteria
The assessment of the achievement of the course objectives includes a WRITTEN and an ORAL test in which a written REPORT on a total synthesis is to be discussed.
The WRITTEN TEST will focus on questions concerning the course contents 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. It will also assess that the student is able to communicate processes and outcomes in writing using discipline-specific terminology.
The WRITTEN TEST is evaluated on a 0-30 scale and will have a weight on the final grade of approx. 80%.
The ORAL TEST, which can be accessed only after passing the written test with a score of not less than 18/30, will have a weight on the final grade of approx. 20%, will focus on the discussion of the WRITTEN REPORT if due, or on short questions by the teacher and will serve to verify/confirm the knowledge acquired by the student as well as the technical/scientific language property used.
The WRITTEN REPORT is a critical commentary of a published total synthesis as well as the key mechanisms and transition states covered in the assigned synthesis. This report is to be done by students on an individual basis. The work is to be handed in to the lecturer in "online" mode no later than two weeks before the date of the call in which the oral examination is to be taken. More information regarding the compilation and verification will be provided during the course and complete instructions will be uploaded on the Course Elly platform.
Completion of the written paper WILL NOT BE REQUIRED if the student has uploaded at least 90 percent of the "TASKS" during the class period.
The final grade will be announced immediately upon completion of the oral examination.
Please note that online registration for the appeal is MANDATORY and that the written test, will be considered valid for the 2-3 months of the exam session period (Jan-Feb or Apr-Jun-Jul, or Sept-Oct-Nov) in which it is passed. After the period has passed without having taken the oral test, it will be necessary to SUBMIT the written test again.
In the two reserved sessions in April and November, written and oral tests must be passed in the same session.
Starting from JANUARY 2024, the abovementioned modalities will be effective also for all students belonging to cohorts prior to 2023-2024, subject to the curricula remaining those of their own cohort of attendance.
Other information
During the course, "homeworks" will be given, which the student will be required to "submit" (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.
