ORGANIC CHEMISTRY LABORATORY AND 3 -MOD.1

The theoretical module 1 of Organic Chemistry 3 is a required course for the master's degree course in Sustainable Chemistry and Technologies, and it deals with reactions, methods, and products of advanced organic chemistry with a focus on aspects of eco-sustainability. In particular, the concepts of advanced organic chemistry are applied to the understanding mechanisms and designing transformations of molecules of renewable origin. Topics addressed include mechanistic aspects, the design of complex organic syntheses, and aspects of eco-sustainability.

1. Knowledge and understanding
i) Classification of reactions according to the different types of selectivity.
ii) knowledge of methods for studying the mechanisms of organic reactions.
iii) knowledge of several advanced synthesis techniques and of different classes of organic reactions and of their mechanisms.
iv) knowledge of direct and retrosynthetic synthetic strategies.
v) knowledge of the reagents of renewable origin and of their chemical transformation/valorization.

2. Ability to apply knowledge and understanding
i) Ability to predict the possible outcomes of different reactions in terms of selectivity and of how to design the related synthetic sequences.
ii) Ability to design experiments aimed at determining the mechanism of an organic reaction.
iii) Ability to describe different classes of organic reactions in terms of reactants, methods, mechanisms, products.
iv) Ability to analyze directly or retrosynthetically the pathways to obtain a product and be able to propose the related coherent sequence of reactions, identifying the most efficient procedures with the lowest environmental impact.
v) Ability to design syntheses starting from reagents of renewable origin.
vi) Ability to read, understand and discuss scientific literature on organic chemistry.

3. Critical skills
i) Ability to identify the reagents and parameters capable of modifying the selectivity of a reaction in the desired way.
ii) Ability to judge whether a reaction mechanism is plausible
iii) Ability to distinguish the most efficient synthetic strategy with the lowest environmental impact.
iv) Ability to understand whether a scientific article is experimentally coherent, and to interpret its data and conclusions.

4. Communication skills
i) Ability to illustrate and explain all aspects of an organic synthesis using the correct scientific terminology and symbology.
ii) Ability to discuss and argue in a logical, coherent and constructive manner with the instructor and with fellow students on the contents of the course.
iii) Ability to explain why certain synthetic paths are chosen rather than others in terms of mechanism, efficiency, and eco-sustainability.
iv) Ability to present and discuss a scientific paper clealy and critically during group activities among strudents..

5. Learning skills
i) Ability to exploit the knowledge acquired to contextualize the contents and to connect the different topics with the aim of identifying the various possible synthetic strategies and choosing the most efficient ones.
ii) Ability to take notes, collect and organize knowledge.
iii) Ability to independently identify the salient aspects of scientific reasoning and the concepts expressed in class.

Having completed Organic Chemistry 1 and 2, including the laboratory. The student must know the structure and properties of the main classes of organic substances; the reactivity of aromatic compounds (aromatic electrophilic substitutions, halogenation and oxidation of side chains, reduction, nucleophilic aromatic substitution), of carboxylic acids and their derivatives (nucleophilic acyl substitution, reductions, etc.); the chemistry of the carbonyl group and derivatives (reduction, oxidation, nucleophilic addition, protection, 1,2 and 1,4 nucleophilic additions, preparation of aldehydes and ketones, additions to aldehydes and ketones, imines, enamines, hydrates and acetals, keto-enol equilibrium, generation of enols and enolates, halogenations, alkylations, malonic and acetacetic synthesis, aldol condensation, Claisen condensation, Michael reaction, conjugate addition of enamines, Robinson annulation), of amines (synthesis and reactivity).

1. Classification of reactions: selectivity (chemo-, regio-), stereo-, stereoselection in C-C bond formation reactions [Laszlo Cap 4; C&S Cap A2]
2. Investigation of organic mechanisms [Norman Cap 4; C&S Cap A4]
3. Protecting groups [Laszlo Cap 5, C&S Cap B13.1]
4. Pericyclic reactions: Diels-Alder cycloadditions, dipolar cycloadditions, sigmatropic rearrangements, ene-reactions, chelotropic eliminations, pericyclic transpositions [Laszlo Cap 7; Norman Ch 9; C&S Cap B6]
5. Rings and heterocycles, strained rings [Laszlo Cap 7; Norman Cap 20]
6. Reductions, oxidations, epoxidations [Laszlo Chap 9, 10; Norman Ch 18, 19; C&S Chap 5, 12]
7. Metal-mediated formation of carbon-carbon bonds [Norman Cap 18; C&S Cap B9]
8. Radical reactions, photochemical reactions; formation and reactivity of carbenes, carbocations and carbanions [Norman Cap 16, 17; C&S Cap B10, A12, A13]
9. Rearrangements [Laszlo Ch 13]
10. Multistep synthesis and synthesis from synthons of renewable origin.

[Laszlo] Pierre Laszlo, “Organic Reactions: Simplicity and Logic” John Wiley & sons, Chichester, 1995 ISBN: 978-0-471-95278-7, 716 Pages.
[Norman] Richard O. C. Norman, James M. Coxon “Principles of Organic Synthesis” 3rd Edition, Chapman & Hall, London 1993 [3rd edition: doi.org/10.1201/9780203742068] 800 pages; in italiano: Richard O. C. Norman, “Chimica organica: principi ed applicazioni alla sintesi” Piccin, Padova
[C&S] Francis A. Carey, Richard J. Sundberg “Advanced organic chemistry. A: Structure and mechanisms” & B: Reactions and synthesis” 3rd ed., New York, Plenum Press, 1990

The final score consists of the grade of module 1 supplemented (in positive or negative) by the grade obtained in the laboratory reports. Submission of the laboratory reports is a requirement to sit the exam of module 1.
The exam of module 1 consists of two parts.
Written exam on the content of the program consisting of 4 exercises (8 points each) to assess basic preparation. The written exam assigns a merit class: A (30-27), B (26-23), C (22-18), D (17-15). It is necessary to obtain at least class D to access the oral exam.
Second oral part: presentation and discussion of an article from the scientific literature, identified by the student through the use of bibliographic search engines, on a topic of advanced organic synthesis in which some of the reagents are eco-sustainable and renewable.
What is evaluated: (1) the ability to identify a scientific article consistent with the purpose of the course, (2) the ability to deepen and explain the topic under consideration, (3) the use of appropriate and precise scientific language, (4) critical ability, (5) the demonstration of being able to write reactions and mechanisms with correct and clear scientific symbology. The oral exam lasts between 20 and 30 minutes.
The final score of the exam is calculated by adding the grade from the written test (75% of the score), the evaluation of the oral test (25%), integrated (positively or negatively) by the grade obtained in the laboratory reports (A=+2, B=+1, C=0, D=-1, E=-2 points). For the laude, one must obtain an A grade in the written test, perform excellently in the oral test, and at least a B grade in the laboratory.

The teaching is organized in lectures including exercises where synthesis and retrosynthesis problemsare solved, accompanied by mechanistic explanation. Anonymous self-assessment tests are conducted at the end of each chapter in the form of a written test followed by correction. Interactive teaching sessions are also conducted through the reading and discussion of material taken from scientific literature.The teaching material is available and downloadable on the University's “Moodle” platform.

Italian

written and oral

This subject deals with topics related to the macro-area "Circular economy, innovation, work" and contributes to the achievement of one or more goals of U. N. Agenda for Sustainable Development