Organic Chemistry 2 and Organic Chemistry Laboratory

A.Y. 2019/2020
10
Max ECTS
112
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
A sufficiently complete insight in the organic reactivity will be given to the student to develop a good knowledge of main reactions and the skill for their correct interpretation.
- The basic preparation will give to the student the ability to elaborate simple synthetic pathways and to fully understand the more complex ones.
- Enough information will be given to the student to understand organic reactions involved in biological processes.
- Provide basic skills for the development of chemical reactions by laboratory activities
Expected learning outcomes
- Knowledge of the main reactions by correctly interpreting the reaction mechanisms.
- Ability to develop simple synthetic patterns from reagents to products
- Use of the skills acquired to tackle advanced organic chemistry courses
- Acquisition of the basic skills necessary to synthesize an organic compound in the laboratory
Course syllabus and organization

Linea AK

Responsible
Lesson period
First semester
Course syllabus
1 - Aromatic compounds. Chemistry of benzene and naphtalene, aromaticity, mechanisms of electrophilic and nucleophilic substitution, activating, deactivating and orienting effects of substituting groups. Understanding of main reactions of synthetic value. Some classes of compounds will be developed taking into account their specific importance.
2 - Chemistry of sulfur containing compounds
3- Enols, enolates, enamines, electron-poor alkenes, quinones: kinetics and thermodynamics of enolization processes, formation and stability of enolates and enamines; synthetic applications of aldol condensation reactions, Claisen condensation reactions, alkylation processes. Theory and use of the reactivity of eletron-poor alkenes.
4 - Heterocyclic compounds. A general picture of the reactivity of several important heterocyclic rings will be given to the student taking into account those essential for his career. Main synthetic pathways will be explained.
5 - Amino acids and peptides: properties of amino acids, their synthesis, protecting groups and principles of peptide synthesis.
6 - Exercises. Theoretical and practical problems will be proposed to the student and solved by direct free discussion.
Laboratory course:

Practical experiences are preceded by the theoretical explanations.
- Basic operations of the Organic Chemistry laboratory: a) Crystallization b) Fractional distillation c) Column chromatography d) Extraction and separation - Examples of preparation of simple compounds with typical techniques and reactions: a) Reduction b) Oxidation c) Nitration d) Diazocopulation e) Aldol and / or Claisen condensation f) Esterification and / or hydrolysis g) Acylation.
All operations and syntheses are followed and controlled with more appropriate routine analytical techniques (TLC, gas chromatography, etc.).
All the products obtained will undergo adequate purification and characterization processes.
Prerequisites for admission
Knowledge of Organic Chemistry I
Teaching methods
Theoretical course: classroom lectures with explanation of the different course topics, followed by interactive exercises on the organic synthesis.

Laboratory practice on the synthesis of simple organic molecules
Teaching Resources
- Slides of the course on Ariel web
- - examples of written tests on the Ariel website
- Testi consigliati: K. P. C. Vollhardt, N. E. Schore, Chimica Organica, Ed. Zanichelli; - P. Y. Bruice Chimica Organica 3a ediz. Ed. Edises 2017 - S. Ege, Chimica Organica, Ed. Sorbona e relativo eserciziario; - J. McMurry, Chimica Organica, Ed. Piccin 9 Ed 2017- R. Norman, J. M. Coxon, Principi di sintesi organica, Ed. Piccin, capitoli scelti. - G. Broggini, G. Zecchi Chimica dei Composti Eterocicli, Ed Zanichelli 2017 - D. Sica, F. Zollo Chimica dei composti eterociclici farmacologicamente attivi, Ed. Piccin.
Assessment methods and Criteria
Written test (15 questions both of theory and applications; two hours; Marks: 0-2 for each question. Minimum to be achieved for oral exam: 17 marks) and oral exam.
The lab evaluation is based on the quality of the practical experiences in lab. and a final report of lab. experiences
The final assessment of the exam is weighed on the basis of the CFU of the theoretical teaching unit (6CFU) and on the laboratory activity (4CFU).
Organic Chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Lessons: 48 hours
Professor: Gelmi Maria Luisa
Organic Chemistry Laboratory
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
Single bench laboratory practical: 64 hours
Shifts:
Turno 1
Professor: Erba Emanuela
Turno 2
Professor: Gelmi Maria Luisa

Linea LZ

Responsible
Lesson period
First semester
Course syllabus
Unità didattica: Chimica Organica 2'.
1- Aromatic compounds. Chemistry of benzene and naphthalene, aromaticity and substituent effects. Mechanisms of electrophilic substitution (halogenation, nitration, sulfonation, Friedel-Craft's alkylation and acylation) and nucleophilic substitution (SnAr, benzyne intermediate). Diazonium salts: synthesis and reactivity. Some classes of compounds will be studied in detail according to their particular importance.
2- Sulfur compounds
3- Enol and enolate chemistry, enamines: termodinamic and kinetic aspects of enolization, enolate and enamines formation and stabilization; synthetic application of base and acid catalyzed aldol reactions, Claisen and Dieckmann condensations. Alkylations, acetoacetic and malonic reactions. Mannich, Henry, Knoevenagel, Wittig reactions and Robinson annulation. Theoretical aspects and reactivity of electron-poor alkenes.
4- Heterocyclic compounds and their nomenclature. A general overview on the reactivity of the most important 5-member (pyrrole, thiophene, furan, oxazole, imidazole, thiazole, isoxazole) and 6-member (pyridine and quinoline) heterocyclic nucleus and their syntheses.
5- Amino acids and peptides: chemical-physical properties and synthesis of amino acids; protecting groups and peptide synthesis.
6- Some lessons will concern theoretical and practical problems and solved by direct free discussion.
Prerequisites for admission
Knowledge of the topics treated in the course of organic chemistry I
Teaching methods
For Learning unit 1: method of work lectures and exercises.
For Learning unit 2: lab practice exercises after lectures.
Teaching Resources
- K. P. C. Vollhardt, N. E. Schore, Chimica Organica, Ed. Zanichelli; - P. Y. Bruice Chimica Organica 3a ediz. Ed. Edises 2017 - S. Ege, Chimica Organica, Ed. Sorbona e relativo eserciziario; - J. McMurry, Chimica Organica, Ed. Piccin 9 Ed 2017- R. Norman, J. M. Coxon, Principi di sintesi organica, Ed. Piccin, capitoli scelti. - G. Broggini, G. Zecchi Chimica dei Composti Eterocicli, Ed Zanichelli 2017 - D. Sica, F. Zollo Chimica dei composti eterociclici farmacologicamente attivi, Ed. Piccin.
- D.L. Pavia, G.M. Lampman, G.S. Kriz "Laboratorio di Chimica Organica" ed. Sorbona - B. S. Furniss, A. J. Hannaford, V. Roger, P. W. Smith, A. R. Tatchell "Vogel Chimica Organica Preatica con analisi qualitativa" II ed, Casa Editrice Ambrosiana.
Assessment methods and Criteria
a) For the Organic chemistry II the exam consists on a written test (including 15 questions, 2 marks for question) and oral examination after getting over the written test.
b) For the Learning unit 2, reports regarding the lab practice exercises.
The final mark consists on the weighted average of the 2 previous scores depending on the CFU of the 2 learning units.
Organic Chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Lessons: 48 hours
Organic Chemistry Laboratory
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
Single bench laboratory practical: 64 hours
Shifts:
Turno 1
Professor: Rossi Elisabetta
Turno 2
Professor: La Rosa Concetta