ORGANIC CHEMISTRY I
Learning outcomes of the course unit
At the end of the course, the student is expected to acquire and strengthen learning and knowledge of basic organic chemistry.
In particular, the student should be capable of:
1. Applying knowledge of the basic functional groups to the classification of simple organic molecules;
2. Knowledge, understanding and applying the structural representation of simple organic molecules and their visualization in the three-dimensional space;
3. Knowledge and understanding of basic physical-chemistry principles (chemical equilibria, structural theory, thermodynamics and kinetics of organic reactions, acids and bases, nucleophiles and electrophiles);
4. Knowledge, understanding and prevision of the relationship between the structure of simple organic molecules and their physical properties, in particular their solubility in aqueous or non-aqueous solvents;
5. Knowledge, understanding and prevision of the relationship between the structure of simple organic molecules and their reactivity, also doing suitable exercises;
6. Knowledge and understanding the methods of synthesis and interconversion of simple organic molecules (containing the functional groups detailed in the contents section) and applying these methods for the synthesis and transformation of unknown organic molecules, also solving simple exercises;
7. Knowledge the international rules for the nomenclature of simple organic molecules and applying them to unknown molecules, also solving simple exercises;
8. Communication skills of the course contents to specialized and non-specialized audience;
9. Understanding the importance of organic chemistry in the study of drugs and living organisms.
To fully appreciate the content of the course, it is necessary to acquire knowledge of general and inorganic chemistry in a previous course. To access the final examination, it is mandatory to pass the “General and Inorganic Chemistry” exam.
Course contents summary
The first part of the course will be devoted to present the fundamentals of organic chemistry emphasizing the key connections between the molecular structure of organic compounds and their physical and chemical properties, as well as their reactivity. Attention will be paid to basic principles of organic chemistry including hybridization and molecular geometry, electronegativity, the nature of chemical bond and polarity of the molecules, acidity and basicity, nucleophilicity and electrophilicity, resonance, isomerism and chirality.
The second part of the course will be devoted to the systematic description of reactivity, physical properties and synthetic methods of the main classes of organic compounds according to their functional group (alkanes, cycloalkanes, alkenes, alkynes, halo-alkanes, alcohols and diols, aldehydes, ketones, etc.). In this context, particular emphasis will be given to the description of reaction mechanisms, highlighting similarities and featuring aspects of different reaction pathways.
General aspects. Origin and development of organic chemistry as a science. Carbon as the focal element in organic chemistry. Functional groups featuring the main organic compound families. Relationships between molecular structure and physical- chemical behavior. Three-dimensional shape of molecules: conformation and configuration of stereogenic centers. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometrical isomers. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Resonance in organic compounds. Radical and ionic reactions. Oxidation and reduction of organic compounds. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry. Monomolecular and bimolecular nucleophilic substitution reactions at saturated carbons. Monomolecular and bimolecular elimination reactions. Solubility and solvents used in organic chemistry. Electrophilic additions to alkenes. Regioselective, stereospecific, and stereoselective organic reactions. Nucleophilic addition to carbon-oxygen double bond. Organometallic compounds and Grignard reagents. Nucleophilic substitution at the carbonyl group (acyl nucleophilic substitution). Enols and enolates: alpha-alkylation and alpha-halogenation. Aromaticity.
Structure, nomenclature, natural occurrence, physical properties, reactivity and synthesis of the following organic compound families: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, diols, ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, lactones, amides, lactams, imides, nitriles, amines, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds.
RECOMMENDED TEXTBOOKS (choose one of the following):
1. W.H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote, “Chimica Organica”, VI Ed., EdiSES, Napoli, 2019.
2. J. McMurry, “Chimica Organica”, IX Edizione, Piccin, Padova, 2017.
3. P. Yurkanis Bruice, "Chimica Organica", III Edizione, EdiSES, Napoli, 2017.
4. Autori vari, “Chimica Organica”, II edizione (a cura di B. Botta), Edi.Ermes, Milano, 2016.
WORKBOOKS (choose one of the following):
1. B.L. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Chimica Organica di Brown, Iverson, Anslyn, Foote", IV Ed., EdiSES, Napoli, 2016.
2. F. Nicotra, L. Cipolla, "Eserciziario di Chimica Organica", Edises, Napoli, 2013.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
4. M.V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Seconda Edizione, Loghia Ed., Napoli, 2009.
1. J. Clayden, N. Greeves, S. Warren, “Organic Chemistry”, Second Edition, Oxford University Press,. 2012.
2. L. Kürti, B. Csakò, “Strategic Applications of Named Reactions in Organic Synthesis”, 1st Edition, Academic Press, 2005.
As additional study tools, slides presented during lessons and copies of the past examination tests will be uploaded and updated in the Elly platform.
The course is carried out through frontal oral lessons at the blackboard or making use of additional teaching material (slides) (total 64 hours corresponding to 8 CFU). Exercises dealing with synthesis and manipulation of simple organic molecules will be proposed and will be carried out by either the teacher or the students. The exercise sessions are open to free discussion between students and teacher and these are considered an essential part of the course to:
-check applying knowledge and understanding of proposed contents;
-apply rules and principles underlying organic reactions to solve practical problems dealing with the contents of the course;
-check learning skills and communication skills.
The student is expected to read and study the contents of the lessons by him/herself by using notes and textbook, and applying this knowledge in the execution of exercises, including both the exercises made in classroom, and exercises in the textbook and study guides.
The teacher is available for further explanations about theory and exercises at the end of the lesson, or in office on e-mail appointment.
The additional material (slides) is weekly loaded on Elly platform; this material does not substitute the textbook and the exercise study guide, which are mandatory.
Many copies of past written tests are loaded and updated in the Elly platform, to provide further tools in preparation of the examination.
Assessment methods and criteria
Knowledge and learning of the student are verified by a final examination that consists of one written test and an oral colloquium.
The written test consists of 4/5 (open-answer) questions dealing with solving problems on the synthesis and reactivity of simple organic compounds. The result is marked in thirtieth, with a minimum pass of 18; it contributes for the 50% of the final quotation of the whole examination.
To access the final oral examination and subsequent recording, it is necessary to pass the written test.
To access the written examination, the student must register on-line (via ESSE3 portal) in the dates according to the official examination schedule of the Food and Drug Department.
The written exam is judged positive (> or equal to 18/30) when the student demonstrates knowledge and learning of the following contents:
-identification and knowledge of the functional groups (as detailed in the contents) within simple organic molecules; identification of carbon stereocenters and chirality;
-applying knowledge and understanding in relating the structural properties and the reactivity of organic compounds;
-applying knowledge and understanding in predicting the outcome of a chemical transformation;
-selecting information from the theory study to analyze and solve a practical organic chemistry problem;
-completing synthesis sequences and interconversion of functional groups of simple organic compounds.
While doing the examination, no books, notes nor whatever information system must be available.
The result of the written examination is given within one week and anyway before the oral examination of that session via ESSE3 portal.
The oral colloquium is intented to test and confirm the student knowledge on the contents of the course, to check communication skills and the correct use of specialized language.
The result of the final exam is the arithmetic mean of both written and oral exams and is marked in thirtieth; a minimum of 18/30 is required as a threshold.