ORGANIC CHEMISTRY
cod. 1004454

Academic year 2014/15
2° year of course - First semester
Professor
Academic discipline
Chimica organica (CHIM/06)
Field
Discipline chimiche
Type of training activity
Basic
56 hours
of face-to-face activities
7 credits
hub: PARMA
course unit
in - - -

Integrated course unit module: ORGANIC CHEMISTRY BASICS - ORGANIC CHEMISTRY

Learning objectives

Aim of the course is to acquire knowledge and understanding, concepts and learning skills within the following domains:
1) students should learn, understand and deepen the basic principles which connect the structure of organic compounds with their physico-chemical properties;
2) students should learn, understand and deepen the principles underlying organic reactions allowing them to rationally interpret reaction mechanisms and to understand similarities and differences among different reaction pathways;
3) students should learn and understand close connections between organic chemistry and neighboring disciplines such as biochemistry and medicinal chemistry;
4) students should select information and ideas in order to make judgments and apply such information to solve ever emerging problems of organic chemistry, to predict the outcome of known (and possibly unknown) organic transformations, to propose ways to design and synthesize simple organic compounds;
5) students should acquire learning skills and communication skills by employing appropriate language to both specialized and non-specialized audience, in line with the above mentioned objectives.
At the end of the course, students having followed all the theory and exercise lessons are expected to be able to applying knowledge and understanding of the above mentioned subject areas through the correct execution of problems and exercises about:
1) recognizing and analyzing the relationship between structure and properties (reactivity) of organic molecules;
2) proposing viable solutions as how to retro-synthesize, synthesize, transform, and interconvert the above mentioned organic compounds.

Prerequisites

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 necessary to pass bot the “General and Inorganic Chemistry” exam and the Organic Chemistry Basics” exam.

Course unit content

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: aldehydes, ketones, carboxylic acids, acyl halides, acid anhydrides, esters, thioesters, lactones, amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on 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 and Mannich addition reactions, 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, and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines, simple aromatic heterocycles, azo-compounds.

Full programme

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 (carbonyl compounds, phenols, aniline), 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: aldehydes, ketones, carboxylic acids, acyl halides, acid anhydrides, esters, thioesters, lactones, amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on 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 and Mannich addition reactions, 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, and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines, simple aromatic heterocycles, azo-compounds.

Bibliography

Textbooks (one of the following to be chosen):
1. W.H. Brown, C.S. Foote, B. L. Iverson, E. V. Anslyn, “Chimica Organica”, IV Edizione, EdiSES, Napoli, 2010.
2. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2011.
3. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2012.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
6. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1997.

Study guide and solution manual for exercises (at least one of the following to be chosen):
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed., Napoli, 2011.
2. B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 3° Ed., EdiSES, Napoli, 2006.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
4. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1998.

Reference books:
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
2. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
Additional teaching material for students:
Examples of organic chemistry exercises given in the previous examination sessions.

Teaching methods

According to the above mentioned objectives and contents, the course is carried out through frontal oral lessons and includes exercises at the blackboard dealing with the design, synthesis, and transformation of simple organic molecules which could be connected with the pharmaceutical and biological domains. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course.

Assessment methods and criteria

The final examination consists of a written exam followed by an oral colloquium (in case the written exam has been passed). The written exam deals with the execution of exercises on the synthesis and reactivity of organic compounds. This test is aimed at verifying whether the student has developed the skill and ability of 1) recognizing the relationship between structure and properties of organic compounds, 2) predicting the behavior of a given organic chemistry transformation among those comprised in the program, 3) selecting and deploying information from the theory study in order to furnish solutions to a given practical organic chemistry problem. The result of the written exam is marked in thirtieth. A minimum of eighteen thirtieth is required as a threshold. Having passed the written exam, a brief colloquium is carried out aimed at verifying the communication skills and the correct use of specialized language.
Since the “Organic Chemistry” course is the sequel of the “Organic Chemistry Basics” course, the final marking is given by the arithmetic mean of the quotations of each part.

Other information

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