Learning objectives
Objectives (in agreement with the Dublin descriptors);
• Knowledge and understanding:
to complete the acquisition, at a basic level, of the: a) the ability to interpret and evaluate the structure, the physical properties and the reactivity of organic molecules; b) the thermodynamic and kinetic aspect of organic reactions and their mechanisms, also for what concerns biomolecules and material science.
• Applying knowledge and understanding:
students will be stimulated to integrate their theoretical knowledge with competences acquired during the classroom lessons and exercises and of the practical experiences in the organic chemistry lab.
• Making judgments:
through a continuous and interactive discussion among themselves and with the teachers, both in the classroom and in the laboratory, students will be accompanied to gradually develop the ability to understand concepts of increasing difficulties and methods to tackle complex organic chemistry problems
• Learning skills:
through a correct use of the scientific and technical language employed during the frontal theoretical lessons, the two hours/week of tutorial and guided exercises, tools to gradually implement the ability of Students to apprehend concepts of increasing complexity will be suggested.
• Communication skills:
an important objective of this course is to accompany all students to acquire a rigorous disciplinary language through which, not only to learn the discipline, but also to efficiently transmit their knowledge and skills either to experts in the field and experts of contiguous disciplines.
Prerequisites
Knowledge of the topics developed in the courses of General and Inorganic Chemistry with Laboratory and of Organic Chemistry.
Course unit content
Heteroaromaticity - Nucleophilic aromatic substitution reactions
Aldehydes and ketones
Carboxylic acids and derivatives
Substitution reactions in alpha to the carbonyl group
Basic concepts of protecting groups
Basic methodologies for the conjugation of organic molecules to biomolecules and materials
Amino acids, peptides, proteins
Carbohydrates
Lipids - Triglycerides, phospholipids, terpenes and steroids.
Nucleic Acids
Full programme
Heteroaromaticity - Aromaticity and Huckel rule for heteroaromatic systems; - 5 and 6 atom heterocycles, characteristics and reactivity: orientation in the electrophilic aromatic substitution reactions; Nucleofilic aromatic subtitution reactions
Aldehydes and ketones – Reactivity: nucleophilic addition and protonation-addition reactions; - Addition reactions of O-nucleophiles (hydration, formation of hemiacetals and acetals), N-nucleophiles (formation of imines, enamines and oximes), C-nucleophiles (synthesis of cyanidrins, alcohols and Wittig reaction); - Nucleophilic Addition to conjugated α, β unsaturated systems, kinetic and thermodynamic control. Michael addition. Aldehydes and ketones as electrophiles in SEAr.
Carboxylic acids and derivatives - Acidity of carboxylic acids, influence of the substituents; - Discussion of nucleophilic acyl substitutions; - Derivatives of carboxylic acids, synthesis and reactivity; - Electrophilic rearrangements towards C, N and O electron deficient atoms.
Substitution reactions in alpha to the carbonyl group - keto-enol tautomerism, reactions of α substitution, halogenations; - Alkylation of enolates: malonic and acetacetic syntheses, direct alkylation; - Condensation reactions of carbonyl compounds, aldol condensation and mixed condensation, Koevenagel condensation. Ester self-condensation (Claisen condensation).
Basic concepts of protecting groups
Multistep synthesis of organic compound through a retrosynthetic approach
Basic methodologies for the conjugation of organic molecules to biomolecules and materials
Amino acids, peptides, proteins - Amino acids: structure and acidity, isoelectric point, titration curve, syntheses of amino acids – Peptides: peptide bond, synthetic strategy for dipeptide preparation, introduction to the solid phase synthesis of peptides; - Introduction to proteins.
Carbohydrates - Classification of carbohydrates, monosaccharides, disaccharides, polysaccharides – Five and six-atom cyclic structures - Stereochemistry, Fisher’s and Haworth’s structures, anomers and epimers; - Acetals and hemiacetals, mutarotation and reducing ability - Glycoside bond: formation and stereochemistry; Cellulose, starch and glycogen.
Lipids - Triglycerides, phospholipids, soaps, terpenes and steroids.
Nucleic Acids - Structure of nucleic acids, nucleosides and nucleotides; - Purine and pyrimidine bases.
Laboratory of Organic Chemistry
Introduction to the organic chemistry laboratory: safety standards in organic chemistry laboratories, introduction to separative analytical techniques (TLC, GC), introduction to spectroscopic techniques (IR and UV), separative laboratory techniques (recrystallization, extraction, distillation).
Laboratory experiences:
* Separation of organic products by acid-base extraction;
* Purification of an organic compound by recrystallization;
* Separation of volatile components by simple distillation;
* Reduction of an aldehyde in the presence of an ester;
* Aldol condensation reaction.
Bibliography
. W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote: Chimica Organica, Casa Ed. Edises, Napoli
For consultation
. J. McMurry - Chimica Organica - Piccin, Padova
. P. Y. Bruice - Chimica Organica - EdiSES, Napoli
And exercises book present in the chemistry library:
- Guida alla soluzione dei problemi da Chimica Organcica, Brown, Iverson, Anslyn, Foote: EdiSES Napoli
- Guida Ragionata allo svolgimento di esercizi di Chimica Organica, M.A. D’Auria, O. Taglialatela Scafati, A. Zampella, Loghia editore
On ELLY, copies of the slides and exercises used in classroom will be available together with few copies and examples of written exams
Teaching methods
- Theory course with analysis and discussion of synthesis exercises. Several hours will be devoted to carry out exercises and exam simulation in the classroom. Students will be prompted to autonomously tackle exercises and synthesis possibly interacting in small groups.
- The laboratory part consists of 10 hours of lectures and 5 practical laboratory experiences for a total of 30 hours. In the lab, where the student will work autonomously, he/she will be prompted to verify the knowledge acquired in classroom and to develop, through a scientific method, the ability to interpret experimental data and to solve practical problems.
Teachers will be available, at the end of the lessons or in the dedicated hours for students colloquia (additional meeting might be fixed by e-mail).
Assessment methods and criteria
The exam is divided in a written exam lasting 2 hours with 6 exercises/problems of organic chemistry, aiming at verifying the ability of the student to autonomously carry out problems connected with the reactivity of the different classes of organic compounds object of the course. The exam will be evaluated with a mark ranging between 0 and 30, with a maximum of 5 points per exercise. Only students receiving a mark higher or equal to 17/30 will be admitted to the oral exam.
During the oral exam will be further discussed some of the problems of the written exams, additional problems not present in the written exam and concepts and experiences carried out in the laboratory module.
It will be evaluated the ability of the student to use a rigorous methodological approach to the reading of the chemical and structural information of the different class of organic compounds and its transfer to the management of their reactivity. In particular the following criteria for the ponderal determination of the final score will be applied:
• Knowledge and ability to comprehend the language and methods of organic chemistry 6/30
• Ability to apply the acquired competences 15/30
• autonomy to tackle problems related to organic chemistry 5/30
• communication ability through a rigorous chemical language 4/30
For the laboratory part (assessed simultaneously to the oral theory part), the laboratory notebook will be evaluated, written up for the last two experiences (50% of the evaluation of the laboratory module). Learning will also be assessed in the form of an oral exam on topics covered during classes and laboratory (remaining 50% of the evaluation of the laboratory module).
Other information
Additional activities:
• The classroom lessons are integrated with tutorial activities (1-2 h/week).
• Two full days of guided exercises are organized before written examinations
• Teachers are willing to receive students every working day (upon arranging the appointment via e-mail)
• All material presented during the course are freely available online (ELLY)
