Learning objectives
At the end of the course, the student is expected to strengthen knowledge of fundamental organic chemistry and acquire learning and knowledge of advanced organic chemistry as a platform for the study of drugs in subsequent classes.
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 of the 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).
Prerequisites
To fully appreciate the content of the course, it is necessary to acquire knowledge of general and inorganic chemistry and organic chemistry fundamentals in previous classes. To access the final examination, it is necessary to pass both the “General and Inorganic Chemistry” examination and the "Organic Chemistry Basics” written examination.
Course unit content
Recall of key topics in the "Organic Chemistry Basics” class. The following topics are then treated.
Topic 5. Classification of solvents. Structure and nomenclature of halogenoalkanes, physico-chemical properties, monomolecular and bimolecular nucleophilic substitution reactions at saturated carbon atoms, monomolecular and bimolecular beta-elimination reactions: mechanisms, predction of resulst based on experimental conditions, competition. Connection with biology, drugs, environment.
Topic 6. Structure, nomenclaure, physico-chemical properties of aliphatic alcohols, ethers, epoxides, thiols, thioethers, amines. Reactivity of alcohols as acids, bases, in SN/E reactions, oxidations. Bried introduction on the reactivity of ethers and thiols. Reactions of epoxide opening. Basic (and acid) properties of amines, amines as nucleophiles. Connection with the natural world and drugs.
Topic 7. Structure of benzene, aromaticity, nomenclature of benzene derivatives, their physico-chemical properties. Reaction of electrophilic aromatic substitution: mechanism and applications. Introduction to phenols and their biological relevance. Aromatic amines: structure, synthesis, and biological properties. Main aromatic heterocycles: structure, resonance, relevance in the world of drugs.
Topic 8. Aldehydes and ketones: structure, nomenclature, physico-chemical properties. Reactivity: nucleophilic addition, addition-elimination with ammonia derivatives, redox reactions. Keto-enol tautomerism. Brief introduction to the structure of aldose and ketose monosaccharides, and di- and polysaccharides.
Topic 9. Carboxylic acids: structure, nomenclature, physico-chemical properties, behaviour as acids. Reactions of acylic nucleophilic substitution: Fischer esterification. brief introduction to reduction reactions and decarboxylation. Connection with the natural world, brief introduction to fatty acids. Main acylic derivatives: structure, nomenclature, SNAc reactions with alcohols and amines, their interconversion, brief introduction to reduction reactions with hydrides and Grignard reagents. Brief introductions to the structure of peptides.
Topic 10. Enolate anoin: structure and formation. Aldol reaction, Claisen condensation, Michael addition. Connection with the natural world and drugs.
Full programme
Recall of key topics in the "Organic Chemistry Basics” class. The following topics are then treated.
Topic 5. Classification of solvents. Structure and nomenclature of halogenoalkanes, physico-chemical properties, monomolecular and bimolecular nucleophilic substitution reactions at saturated carbon atoms, monomolecular and bimolecular beta-elimination reactions: mechanisms, predction of resulst based on experimental conditions, competition. Connection with biology, drugs, environment.
Topic 6. Structure, nomenclaure, physico-chemical properties of aliphatic alcohols, ethers, epoxides, thiols, thioethers, amines. Reactivity of alcohols as acids, bases, in SN/E reactions, oxidations. Bried introduction on the reactivity of ethers and thiols. Reactions of epoxide opening. Basic (and acid) properties of amines, amines as nucleophiles. Connection with the natural world and drugs.
Topic 7. Structure of benzene, aromaticity, nomenclature of benzene derivatives, their physico-chemical properties. Reaction of electrophilic aromatic substitution: mechanism and applications. Introduction to phenols and their biological relevance. Aromatic amines: structure, synthesis, and biological properties. Main aromatic heterocycles: structure, resonance, relevance in the world of drugs.
Topic 8. Aldehydes and ketones: structure, nomenclature, physico-chemical properties. Reactivity: nucleophilic addition, addition-elimination with ammonia derivatives, redox reactions. Keto-enol tautomerism. Brief introduction to the structure of aldose and ketose monosaccharides, and di- and polysaccharides.
Topic 9. Carboxylic acids: structure, nomenclature, physico-chemical properties, behaviour as acids. Reactions of acylic nucleophilic substitution: Fischer esterification. brief introduction to reduction reactions and decarboxylation. Connection with the natural world, brief introduction to fatty acids. Main acylic derivatives: structure, nomenclature, SNAc reactions with alcohols and amines, their interconversion, brief introduction to reduction reactions with hydrides and Grignard reagents. Brief introductions to the structure of peptides.
Topic 10. Enolate anoin: structure and formation. Aldol reaction, Claisen condensation, Michael addition. Connection with the natural world and drugs.
Bibliography
Choose ONE of the following textbooks (MANDATORY) (the same for both modules):
1. W.H. Brown, T. Poon, “Introduzione alla Chimica Organica”, VII Edizione, EdiSES Università, Napoli, 2023
2. J. Gorzynski Smith, "Fondamenti di Chimica Organica", Quarta Edizione, McGraw-Hill Education, 2023
3. P.Y. Bruice, "Elementi di Chimica Organica", III Edizione, EdiSES Università, Napoli, 2024
Further readings for consultation (at the library of the Science Centre in the Campus):
-W.H. Brown, B. L. Iverson, E. V. Anslyn, C.S. Foote, “Chimica Organica”, VII Edizione, EdiSES, Napoli, 2023
-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. Clayden, N. Greeves, S. Warren, , “Chimica Organica”, Piccin, 2023
-R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a EdizioneItaliana, Piccin Editore, Padova, 1997
-L. Kürti, B. Czakó, “Strategic Applications of Named Reactions in Organic Synthesis”, Elsevier Academic Press, 2005.
Further material loaded on Elly includes:
-slides of each lesson;
-exercises for each subject matter;
-some copies of the text of written examinations of the past academic years
Teaching methods
The present course is realized with frontal lessons (both theory and exercises) via IN-PRESENCE modality. In particular, the teacher takes lessons in the classroom with the help of PC (Powerpoint slides); the lesson slides are uploaded in Elly.
The teacher also performs exercises (in classroom with the collaboration of students) 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 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, some 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 about 6
(open-answer) questions 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. The laude (30/30 cum laude) is assigned as a maximum quotation when all questions are correctly answered and when specialized language is used.
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.
The written examination is performed IN PRESENCE. 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.
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, according to the guidelines of CAI.
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.
Once written examinations of both modules are passed, the student must attend the final oral examination IN PRESENCE (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.
Other information
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2030 agenda goals for sustainable development
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