Learning outcomes of the course unit
At the end of the course, the student is expected to strengthen knowledge of basic organic chemistry and acquire learning and knowledge of advanced organic chemistry as a platform for the study of subsequent courses and for the study of drugs.
In particular, the student is expected to achieve the following targets:
1. knowledge of the basic and advanced functional groups and application of this knowledge for the classification of simple polyfunctionalized organic molecules ((knowledge and understanding; applying knowledge and understanding);
2. application basic physical-chemistry principles (chemical equilibria, structural theory, thermodynamics and kinetics of organic reactions, acids and bases, nucleophiles and electrophiles) to simple polyfunctionalized organic molecules (applying knowledge and understanding);
3. knowledge, understanding and prevision of the relationship between the structure of simple polyfunctionalized organic molecules (containing the functional groups detailed in the contents section) and their physical properties, in particular their solubility in aqueous or non-aqueous solvents (knowledge and understanding; applying knowledge and understanding);
4. knowledge, understanding and prevision of the relationship between the structure of simple organic molecules (containing the functional groups detailed in the contents section) and their reactivity, also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
5. knowledge and understanding the methods of synthesis (preparation) and interconversion of simple polyfunctionalized organic molecules (containing the functional groups detailed in the contents section) and application of these methods to the synthesis and transformation of unknown organic molecules, also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
6. knowledge of the international rules for the nomenclature of simple polyfunctionalized organic molecules (containing the functional groups detailed in the contents section) and application of them to unknown molecules, also by solving suitable exercises (knowledge and understanding; applying knowledge and understanding);
7. ability to convey the contents of the course to a specialized audience using appropriate scientific language (both written and oral) (communication skills);
8. understanding the role of organic chemistry in the study of drugs and living organisms. Acquire ability to link the contents of the course to those of neighboring chemical disciplines (making judgements; learning skills).
To fully appreciate the content of the course, it is necessary to acquire knowledge of general and inorganic chemistry and organic chemistry basics in previous courses. To access the final examination, it is mandatory to pass both the “General and Inorganic Chemistry” examination and the Organic Chemistry Basics” written examination.
Course contents summary
The first part of the course is devoted to recall and advance knowledge acquired in the "Organic Chemistry Basics” course. The following subjects are then treated: nucleophilic addition to carbon-oxygen double bond, acyl nucleophilic substitution, brief description of the role of protecting groups in organic synthesis, brief survey of qualitative identification of the main functional groups. The systematic study of the following compound classes is then placed, comprising the structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkyl halides, alcohols, diols, thiols, ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, acid anhydrides, esters, thioesters (briefly), lactones, amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives (briefly).
The second part of the course allows students to learn carbon-carbon bond-forming reactions, synthesis of enols and enolates, imines and enamines, alpha-alkylation and alpha-halogenation of enols and enolates, aldol additions and condensations and variants thereof, Claisen condensations and related reactions, Michael addition reaction, examples of transposition reactions.
The third part of the course allows students to acquire knowledge on the aromatic domain including the concept of aromaticity and the systematic study of aromatic compounds including the structure, nomenclature, natural occurrence, physical properties, reactivity (aromatic electrophilic substitution, aromatic nucleophilic substitution), and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines, simple aromatic heterocycles, azo-compounds.
Lastly, the following topics will be briefly surveyed: amino acids and peptides, monosaccharides (cyclic structures, glucose), disaccharides and oligosaccharides. Brief introduction on fatty acids, triglycerides.
Recalling the contents of the previous course of Organic Chemistry Basics.
Alkyl halides, alcohols, diols, thiols, ethers, epoxides: structure, synthesis, reactivity.
Carbonyl Compounds, the carbon-oxygen double bond. Aldehydes and ketones, structure, resonance, keto-enolic tautomerism, occurrence in Nature, physical properties. Nucleophilic additions: formation of geminal diols, hemiacetals, acetals, cianhydrins, reactions with Grignard reagents (mechanisms). Brief introduction to protecting groups of carbonyl compounds. Brief introduction to the hemiacetal structure of simple monosaccharides such as glucopyranose. Reactons of aldehydes and ketone with nitrogen nucleophiles: formation of imines, iminium ions, hydrazones, oximes (mechanisms). Reactions of aldehydes and ketones con reducing agents; reactions with oxidant reagents (mechanisms). Baeyer-Villiger reaction (no mechanism). Wittig reaction (mechanism). Synthesis methods for aldehydes and ketones.
Carboxylic acids and derivatives. Examples of fatty acids. Structure, nomenclature, physical properties, occurrence in nature of carboxylic and bicarboxylic acids, acyl halides, anhydrides, esters, lactones, amides, lactams, nitriles, carboxylate ions. Brief introduction on the sulfur counterparts (sulfonic acids and esters, thioesters). Reaction of acyl nucleophilic substitution of carboxylic acids and derivatives with nucleophiles (water, alcohols, amines), reactions with hydrides, with organometallic reactants (Grignard, organocuprates) (mechanisms).
Acidity of carboxylic acids, factors which influence the acidity.
Methods of synthesis of carboxylic acids including reaction with CO2, nitrile hydrolysis, malonic synthesis, saponification. Synthesis of acyl halides, anhydrides, esters, amides, nitriles. Brief introduction on the amide (peptide) linkage between amino acids.
Reactions involving the alpha-carbon of enolizable carbonyl compounds: formation of enols, enolates, enamines. Alpha-halogenation of ketones; alpha-alkylation of ketones (direct, acetoacetic synthesis, via enamine) (mechanisms).
Aldol addition and aldol condensation reaction (inter- ad intramolecular) (mechanisms).
Claisen condensation and related reactions (mechanisms).
Carbon-carbon bond-forming reactions.
Alpha,beta-unsaturated compounds: structure, resonance, synthesis, 1,2 versus 1,4 reactivity with nucleophiles. Michael reaction (mechanisms).
Carbonic acid derivatives: brief introduction to functional groups including carbonates, carbamates, urea, carbamic acid.
Phosphorus and sulfur derivatives: brief introduction to functional groups including phosphates, phosphonates, phosphites, phosphines, sulfates, sulfonates, sulfoxides, sulfones, sulfides.
Aromatic compounds. Concept of aromaticity. Huckel rule. Structure, nomenclature, natural occurrence, physical properties and reactivity of benzene. Reactions of aromatic electrophilic substitution (halogenation, nitration, sulfonation, Friedel-Crafts alkylation, Friedel-Crafts acylation, Gatterman-Koch reaction) (mechanisms).
Reactions of aromatic electrophilic substitution on mono- and poly-substituted benzenes: activation/deactivation and orientation effects by pre-existing groups on the benzene ring (mechanisms).
Phenols: structure, acidic properties, nucleophilic properties. Reactions of aromatic electrophilic substitution. Protection of the phenolic group. Synthesis methods.
Aryl halides: structure, aromatic nucleophilic substitution reaction (briefly).
Aliphatic and aromatic amines: structure, nomenclature, natural occurrence, physical properties, basic properties. Relationship between basic properties and structure. Nucleophilic properties (mechanisms). Aniline, protection methods. Reactivity with nitrosonium ion. Benzendiazonium salts: substitution reactions and copulation to azo-compounds (briefly).
Aromatic heterocyclic compounds: structure, resonance, tautomeric forms and nomenclature of simple mono- and bicyclic derivatives.
Choose ONE of the following textbooks (mandatory) (the same for both modules):
-W.H. Brown, B. L. Iverson, E. V. Anslyn, C.S. Foote, “Chimica Organica”, VI Edizione, EdiSES, Napoli, 2019
-P.Y. Bruice, “Chimica Organica”, Terza Edizione, EdiSES, Napoli, 2017
-Autori vari, “Chimica Organica” (a cura di B. Botta), Seconda Edizione, Edi.Ermes, Milano, 2016
-J. Gorzynski Smith, Fondamenti di Chimica Organica, Terza Edizione, McGraw Hill Education, Milano, 2018
-J. McMurry, “Chimica Organica”, IX Edizione, Piccin, Padova, 2017
Choose ONE of the following exercize books (mandatory) (the same for both modules):
-M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Quinta Edizione, Loghia Ed.,Napoli, 2020
-B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 4° Ed., EdiSES, Napoli, 2016
-T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010
-F. Nicotra, L. Cipolla “Eserciziario di Chimica Organica”, Edises, 2013
Further readings for consultation (at the library of the Department of Food and Drug):
-J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001
-R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997
--L. Kürti, B. Czakó, “Strategic Applications of Named Reactions in Organic Synthesis”, Elsevier Academic Press, 2005.
Further material for exercises and examples of the final written examination are loaded on Elly portal:
-exercises (with separate solutions) for each subject matter;
-many copies of the text of written examinations (with separate solutions) of the past academic years.
According to the regulation of the Italian Government and the University of Parma about the COVID-19 pandemics, the present course is realized with frontal lessons (both theory and exercises) via mixed in-presence and at-distance modality. In particular, the teacher takes lessons in the classroom with the help of PC (Powerpoint slides) and board (either graphic table connected to the PC or blackboard); simultaneous connection of the PC to the Teams platform in streaming modality ensures connection with students not present in the classroom. Each lesson is registered and loaded in the Elly portal of the course, together with the slides. The teacher also performs exercises (in classroom with the collaboration of students and simultaneous streaming connection via Teams) in order for the student to: 1) apply the theory to solve exercises dealing with the contents of the course; 2) verify the status of knowledge before passing to the subsequent subject; 3) acquire a method for the execution of exercises in both the synthetic direction (synthesis of a target molecule), and retrosynthetic direction (disconnection of a target molecule).
The student is expected to read and study the contents of the lessons by him/herself by using notes/slides and textbook, and applying this knowledge in the execution of exercises, including 1) the exercises made in classroom, 2) exercises in the textbook and study guides, and 3) exercises assigned during lessons and loaded weekly on the Elly platform. Solutions of exercises are subsequently given by the teacher, for self-evaluation of the students. In addition, many copies of the text of written examinations of the past academic years are loaded and updated in the Elly platform (with solutions), to provide further tools in the preparation of the examination.
The teacher is available for further explanations about theory and exercises in the following moments: 1) at the end or during the break of the lesson, 2) in office or by distance via Teams after e-mail appointment, 3) via chat on Elly platform.
Assessment methods and criteria
To verify the level of knowledge and learning of the student, a written examination is mandatory (2 hour maximum length) consisting of 4-5 (open-answer) questions having different weight and corresponding to a score detailed in the text. The result is marked in thirtieth, with a minimum pass of 18; it contributes for the 45% of the final quotation of the whole examination.
To access the final oral examination and subsequent recording of the integrated course Organic Chemistry Basics /Organic Chemistry, it is necessary to pass the written examination of both modules. It is possible to perform the written examination of both modules in the same date, since they are given at different and subsequent times.
To access the written examination, the student must register on-line (via Essetre) in the dates according to the official examination agenda of the Department of Food and Drug.
In case the COVID-related sanitary emergence continues, the written examination will proceed as follows: 1) written examination in the classroom (whenever possible); 2) remote written examination on the Teams platform (see the guidelines at the address: http://selma.unipr.it/). The teacher will give the students detailed instructions on the modality to access the examination by remote location (link, ID loading, honour declaration loading). Whichever the modality of the examination (in presence or remote), no books, notes, nor web-related material are permitted during the examination; possible compensatory material will be allowed to students with DSA or BES, which will be agreed upon with the teacher at least one week before the examination.
The written exam is judged positive (superior or equal to 18/30) when the student demonstrates knowledge and learning of the following contents: 1) identification and knowledge of the functional groups (as detailed in the contents) within natural or drug-like polyfunctional molecules; 2) identification of carbon stereocenters and chirality; 3) knowledge of the main aromatic and heteroaromatic cyclic compounds with the corresponding resonance structures; 4) execution (even partial) of exercises on synthesis sequences and interconversion of functional groups; 5) execution (even partial) of exercises on the total synthesis of simple organic compounds. The laude (30/30 cum laude) is assigned as a maximum quotation when all questions are correctly answered and when specialized language is used.
The result of the written examination is usually given within one week from the date of the same exam and anyway before the oral examination of that session via Essetre portal. The student is expected to view his/her work (either passed or failed) which is consigned on the day of the oral session either in presence or by distance via Teams. If the student cannot be present that day, he/she has to inform the teacher by e-mail; the teacher will show the work to the student on another date, to be fixed with the student.
Once written examinations of both modules are passed, the student must attend the final oral examination either in presence or by distance via Teams platform (10-20 minutes, 10% weight) in the date of the same session of the last written examination. The on-line registration via Essetre to access the oral examination is suggested but not mandatory.