Organic chemistry

A.Y. 2019/2020
8
Max ECTS
88
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
The course aims to provide students with the basic knowledge of Organic Chemistry, useful for addressing any study path following the first interfaculty year. The laboratory exercises are intended to provide the student with the fundamental knowledge to carry out, effectively and safely, practical activities typical of an organic chemistry laboratory.
Expected learning outcomes
Knowledge and understanding
· know the graphic representation models of organic molecules and reaction mechanisms
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the main reactions of organic molecules, recognize simple equipment in an organic chemistry lab, know the main techniques of preparation and purification of organic compounds
· know the safety regulations in force in a chemical laboratory
Ability to apply knowledge and understanding
· know how to correctly interpret the IUPAC name of the main classes of organic molecules
· recognize the main types of chemical reactions and know how to complete reaction schemes
· be able to conduct a laboratory experience using simple equipment, including data processing
Judgment capacity
· Ability to critically evaluate hypotheses concerning the interaction/transformation modalities of organic molecules relevant in the field of biotechnologies
· ability to assess the risk related to conducting a laboratory experiment
Communication skills
· communicate effectively, orally and in written form, correctly using terminology and graphic models typical of organic chemistry
· share an experimental laboratory space
Learning ability
· ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem
· ability to understand an experimental recipe and translate it into practical operations
Course syllabus and organization

Linea AL

Responsible
Lesson period
Second semester
Course syllabus
Theoretical lessons and classroom exercises
Introduction: Atom hybridization, bond types, bond polarity, resonance forms. IUPAC Nomenclature of the main classes of compounds.
Acid-base reactions in organic chemistry, analysis of acid-base equilibria, relationship between molecular structure and acidity strength.
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes. Naturally occurring hydrocarbons (terpenes).
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomers and diastereoisomers. Optical activity. Polarimetry. Resolution of racemic mixtures. Cahn/Ingold/Prelog nomenclature. Conformational isomerism in linear and cyclic alkanes.
Nucleophilic Substitution reactions. Haloalkanes. SN1and SN2 reactions. Carbocation stability. Factors influencing the reaction mechanism.
Elimination reactions. E2 and E2 reactions. Factors influencing the reaction mechanisms. Competition between substitution and elimination.
Electrophilic Addition reactions to the double bond. Halogenation, hydration, halogen hydride addition, catalytic hydrogenation.
Alcohols, thioles, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic and heterocyclic compounds. Benzene: resonance and electronic structure of the benzene ring. The influence of an aromatic ring to bonded C, N and O atoms. Acidity of phenols. Aromatic electrophilic substitution reactions: halogenation, nitration and sulphonation. Heterocyclic compounds.
Amines. Basicity and acidity. Nucleophilic behaviour and reactivity.
The carbonyl group. Oxidation and reduction reactions in organic chemistry. Aldehydes and ketones. Nucleophilic additions. Keto-enolic tautomerism. Enolate ions. Aldolic reaction.
Carbohydrates. Nomenclature. Monosaccharides, disaccharides e polysaccharides. Aldoses e ketoses. D- and L-series. Hemiacetalic structures. Mutarotation. Glycosides.
Carboxylic acids and their derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Esters. Amides. Nitriles. Synthesis and reactivity: addition/elimination reactions.
Amino acids. Acidity e basicity. D- and L-series. The peptide bond. Problems concerning the chemical synthesis of peptides. Proteins.
Lipids. Saturated and unsaturated fatty acids. Triglycerides. Soaps and detergents.
Nucleic acids. purine and pyrimidine bases and their nucleosides and nucleotides.

Practical laboratory exercises
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid / base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column chromatography.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of a process of organic synthesis (i.e. stoichiometric calculations, dilutions, heating / cooling of the reaction environment, verification of the progress of the reaction, isolation of the product, purification, evaluation of the purity of the product obtained).
Prerequisites for admission
General and inorganic chemistry
Teaching methods
Theory 5 ECTS; Excercises 1 ECTS; Laboratory 2 ECTS
Teaching Resources
The teacher will publish the teaching material of each lesson on the ARIEL website.

Textbooks (Teachers do not express a specific preference over any of the following textbooks)
· Brown, W.H.; Poon, T. "Introduzione alla Chimica Organica" ed. Edises
· Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
· Botta, B. "Chimica Organica Essenziale" ed. edi-ermes
· J. Gorzynski Smith "Fondamenti di Chimica Organica" ed. Mc- Graw - Hill
· McMurry, J. "Fondamenti di Chimica Organica" ed. Zanichelli
Problem-solving textbooks:
· Felix S. Lee, Guida alla soluzione dei problemi da "Introduzione alla Chimica Organica"
ed. Edises (4° ediz.)
Assessment methods and Criteria
The knowledge acquired by the students will be verified through a written test and an oral test. After completing approximately half the program, a partial test will be scheduled to ascertain the student's actual learning level.
The written exam will be divided into two parts. The first will include multiple-answer exercises (20 questions from 0.75 points each, no answer 0, wrong answer -0.25) on the program held in class up to the first partial test. The second will focus on the program carried out in the second half of the course. It will consist of five open-ended exercises, one of which will be inherent to practical laboratory. Each open-ended exercise will be worth 3 points. The student will have at least one hour for each part (at least two hours for the whole written exam). Passing the exam requires the achievement of at least 8/15 in each of the two parts and the overall grade of 18/30.
The oral exam will consist in a discussion of the written exam. In case of uncertainty, or when specifically asked by the student, the oral examination will be extended to questions concerning theoretical aspects of a specific subject or the solution of one or more exercises like those treated during the class lectures and tutorials.
The final result will also take into account the evaluation obtained for practical laboratory exercises. The student will be evaluated based on her/his general behavior during the laboratory exercises and on the completeness/correctness of the reports to be presented at the end of the exercises themselves.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Shifts:
Professor: Contini Alessandro
Turno 1
Professor: Contini Alessandro
Turno 2
Professor: Pellegrino Sara
Turno 3
Professor: Pellegrino Sara

Linea MZ

Responsible
Lesson period
Second semester
Course syllabus
Introduction: Atom hybridization, bond types, bond polarity, resonance forms. IUPAC Nomenclature of the main classes of compounds.
Acid-base reactions in organic chemistry, analysis of acid-base equilibria, relationship between molecular structure and acidity strength.
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes. Naturally occurring hydrocarbons (terpenes).
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomers and diastereoisomers. Optical activity. Polarimetry. Resolution of racemic mixtures. Cahn/Ingold/Prelog nomenclature. Conformational isomerism in linear and cyclic alkanes.
Nucleophilic Substitution reactions. Haloalkanes. SN1and SN2 reactions. Carbocation stability. Factors influencing the reaction mechanism.
Elimination reactions. E2 and E2 reactions. Factors influencing the reaction mechanisms. Competition between substitution and elimination.
Electrophilic Addition reactions to the double bond. Halogenation, hydration, halogen hydride addition, catalytic hydrogenation.
Alcohols, thiols, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic and heterocyclic compounds. Benzene: resonance and electronic structure of the benzene ring. The influence of an aromatic ring to bonded C, N and O atoms. Acidity of phenols. Only mention of aromatic electrophilic substitution reactions. Heterocyclic compounds.
Amines. Basicity and acidity. Nucleophilic behaviour and reactivity.
The carbonyl group. Oxidation and reduction reactions in organic chemistry. Aldehydes and ketones. Nucleophilic additions. Keto-enolic tautomerism. Enolate ions. Aldolic reaction. Michael conjugate addition.
Carbohydrates. Nomenclature. Monosaccharides, disaccharides e polysaccharides. Aldoses e ketoses. D- and L-series. Hemiacetalic structures. Mutarotation. Glycosides.
Carboxylic acids and their derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Esters. Amides. Nitriles. Synthesis and reactivity: addition/elimination reactions. Claisen condensation.
Amino acids. Acidity e basicity. D- and L-series. The peptide bond. Proteins.

Laboratory course
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid / base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column chromatography.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of a process of organic synthesis (i.e. stoichiometric calculations, dilutions, heating/cooling of the reaction environment, verification of the progress of the reaction, isolation of the product, purification, evaluation of the purity of the product obtained).
Prerequisites for admission
Attendance of General and Inorganic Chemistry course
Teaching methods
The course is delivered by classroom lectures (5 CFU), classroom exercises (1 CFU), and laboratory (2 CFU).
Teaching Resources
Textbooks (Teacher does not express a specific preference over any of the following textbooks)
· Brown, W.H.; Poon, T. "Introduzione alla Chimica Organica" ed. Edises
· Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
· Botta, B. "Chimica Organica Essenziale" ed. edi-ermes
· J. Gorzynski Smith "Fondamenti di Chimica Organica" ed. Mc- Graw - Hill
· McMurry, J. "Fondamenti di Chimica Organica" ed. Zanichelli
Problem-solving textbooks:
· Felix S. Lee, Guida alla soluzione dei problemi da "Introduzione alla Chimica Organica"
ed. Edises (4° ediz.)
Assessment methods and Criteria
The knowledge acquired by the students is verified through a written test and an oral test. After completing approximately half the program, a partial test will be scheduled to ascertain the student's actual learning level.
Written test: the written exam will be divided into two parts. The first part will include multiple-answer exercises (20 questions from 0.75 points each, no answer 0, wrong answer -0.25) on the program held in class up to the first partial test. The second part will focus on the program carried out in the second half of the course. It will consist of five open-ended exercises, one of which will be inherent to practical laboratory. Each open-ended exercise will be worth 3 points. The student will have at least one hour for each part (at least two hours for the whole written exam). Passing the exam requires the achievement of at least 8/15 in each of the two parts and the overall grade of 18/30.
Oral test: the oral exam consists in a discussion of the written exam. In case of uncertainty, or when specifically asked by the student, the oral examination will be extended to questions concerning theoretical aspects of a specific subject or the solution of one or more exercises like those treated during the class lectures and tutorials.
The final result will also take into account the evaluation obtained for practical laboratory exercises. The student will be evaluated based on her/his general behaviour during the laboratory exercises and on the completeness/correctness of the reports to be presented at the end of the exercises themselves.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Shifts:
Professor: Lay Luigi
Turno 1
Professor: Sello Guido Giovanni
Turno 2
Professor: Sello Guido Giovanni