Organic chemistry

A.Y. 2018/2019
8
Max ECTS
88
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
The aim of this course is to provide the student with a basic knowledge of Organic Chemistry. With such background, the student will be able to face all kinds of biotechnology course addresses, offered after the first interfaculty year.
Expected learning outcomes
Undefined
Course syllabus and organization

Linea 1

Responsible
Lesson period
Second semester
Course syllabus
class lectures (40 hours)
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, thioalcohols, 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.

Class tutorials (24 hours)
Class tutorials will be held in order to provide a better and deeper understanding of theoretical concepts discussed during the class lectures
Laboratory tutorials (24 ore)
- Introduction to the laboratory tutorials. Basic security rules in a chemistry laboratory. Main purification techniques: distillation and crystallization.
- Main separation techniques: solvent extraction ed extractions with aqueous solutions at variable pH.
- Chromatography. Stationary and mobile phases. Silica chromatography: Column and Thin Layer Chromatography (TLC). Principles and applications.
- Practical examples of organic reactions

EXAMINATION PROGRAMME AND ORGANIZATION
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.
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: Contini Alessandro
Turno 3
Professor: Pellegrino Sara

Linea 2

Responsible
Lesson period
Second semester
Course syllabus
class lectures (40 hours)
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, thioalcohols, 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.

Class tutorials (24 hours)
Class tutorials will be held in order to provide a better and deeper understanding of theoretical concepts discussed during the class lectures
Laboratory tutorials (24 ore)
- Introduction to the laboratory tutorials. Basic security rules in a chemistry laboratory. Main purification techniques: distillation and crystallization.
- Main separation techniques: solvent extraction ed extractions with aqueous solutions at variable pH.
- Chromatography. Stationary and mobile phases. Silica chromatography: Column and Thin Layer Chromatography (TLC). Principles and applications.
- Practical examples of organic reactions

EXAMINATION PROGRAMME AND ORGANIZATION
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.
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