ORGANIC CHEMISTRY LABORATORY AND 3 -MOD.1

The theoretical course (module 1) of Organic Chemistry 3 characterizes the master's degree course in Sustainable Chemistry and Technologies. It aims to open a window on advanced methods for modern and greener organic synthesis.
It provides advanced skills in organic chemistry to address synthetic problems by dealing with the design of complex organic syntheses as well as with the mechanistic and green aspects.

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 reactivity.

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.
iii) Ability to design syntheses starting from reagents of renewable origin.

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.

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.

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 grade of this two- module course is composed by the grade of the oral examination of module 1 and by the grade of the written reports of the laboratory module 2. Failiure to submit the laboratory reports will result in not being able to sit the oral exam of module 1.
The oral exam consists of questions on the entire program. The student can choose between Italian and English. The student must demonstrate knolwedge of the subject and ability to illustrate the topic using the appropriate scientific language and the ability to correctly write the reactions and the mechanisms. The oral exam lasts between 20 and 40 minutes depending on to the clarity and consistency of the answers.
The following are evaluated: 1) knowledge of the topics (reactions, mechanisms, structures, classifications); 2) understanding (concepts, synthetic strategies, reactivity, connections, logical reasoning); 3) the ability to apply knowledge to problems; 4) the ability to analyze, synthesize and formulate judgments; 5) scientific language.
The final score of the exam consists of the grade of the oral exam of module 1, implemented (in positive or negative) by the grade obtained in the laboratory reports.

The teaching is organized in lectures including exercises where synthesis and retrosynthesis problemsare solved, accompanied by mechanistic explanation. The teaching material is available and downloadable on the University's “Moodle” platform.

Italian

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