Organic Chemistry
A.Y. 2018/2019
Learning objectives
The course of Organic Chemistry and Laboratory of Organic Chemistry consists of 52 hours of lectures and 24 hours of laboratory exercises. In the course, all classes of organic compounds are presented, describing their chemico-physical characteristics, the reactivity as well as some preparation method. Knowledge of carbohydrates, amino acids, and nucleotides will be increased.Particular attention is dedicated to stereochemistry, with the recognition of chiral molecules and assessments of their reactivity.All the topics discussed are followed by classroom exercises.
Expected learning outcomes
The main purpose of the course is to enable the student to recognize the class of belonging of every organic molecule and thus to predict its reactivity in the biological field as well. In addition, the course provides the minimum cognitive tools for predicting or explaining supramolecular interactions among organic molecules.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course cannot be attended as a single course. Please check our list of single courses to find the ones available for enrolment.
Course syllabus and organization
Single session
Lesson period
Second semester
Course syllabus
Introduction: Orbital hybridization, bond polarity, resonance forms, IUPAC nomenclature of the main classes of organic compounds.
Acid-Base reactions: chemical equilibrium, molecular structure and pH
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z. Nomenclature Cycloalkanes. Hydrocarbons from natural sources.
Stereochemistry: Symmetry and chirality. Stereogenic centers. Configuration at tetrahedral atoms.Cahn/Ingold and Prelog rules. Configuration at double bonds. Chirality and optical activity. Absolute configuration. Conformational isomers.
Nucleophilic substitution: SN2 and SN1reactions. Stability of carbocations. Reaction mechanisms
Elimination reactions: E1 and E2 mechanisms. Structure-reactivity features of E1 and E2 mechanisms. Competition between substitution and elimination.
Addition to double bonds: electrophilic addition of water, hydrogen halides, Hydrogenation.
Alcohols, thioalcohols, ethers, thioethers: Nomenclature. Physical properties, Acidity and basicity. The S-S bond.
Carbonyl group: Oxidation and Reduction in Organic Chemistry. Aldehydes and Ketones. Nucleophilic addition reactions to the carbonyl group. Keto-enolic tautomerism. Enolates. Aldol condensation.
Carboxylic Acids and derivatives: classification. Acidity. Physical properties. Acyl halides. Organic acid anhydride. Esters. Amides. Nitriles. Synthesis and reactivity.
Aromatic and heterocyclic compounds: benzene, benzene derivatives and main heterocyclic compounds. Resonance and electronic structure.
Electrophilic aromatic substitutio. Effects of substituent groups in the electrophilic aromatic substitution. Acidity of phenols.
Amines: Properties as bases. Reactivity as nucleophiles
Carbohydrates: Monosaccharides, disaccharides and polysaccharides. Aldoses and ketoses. D and L series. Mutarotation. Glycosides.
Aminoacids: Acidity and basicity.L and D series. Peptide bond. Peptide synthesis. Proteins.
Lipids: Saturated and unsaturated fatty acids. Triglycerides. Soaps
Nucleic acids: Nucleosides, nucleotides and nucleic acids
Organic Compounds of biological interest: Purines and pyrimidines.
Laboratory experience:
Introduction. Purification, distillation and crystallization techniques.
Separation techniques. Extraction at variable pH
Chromatography. Stationary and mobile phase. Silica gel chromatography: Tlc and column chromatography. Principles and applications
Examples of organic reactions
Acid-Base reactions: chemical equilibrium, molecular structure and pH
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z. Nomenclature Cycloalkanes. Hydrocarbons from natural sources.
Stereochemistry: Symmetry and chirality. Stereogenic centers. Configuration at tetrahedral atoms.Cahn/Ingold and Prelog rules. Configuration at double bonds. Chirality and optical activity. Absolute configuration. Conformational isomers.
Nucleophilic substitution: SN2 and SN1reactions. Stability of carbocations. Reaction mechanisms
Elimination reactions: E1 and E2 mechanisms. Structure-reactivity features of E1 and E2 mechanisms. Competition between substitution and elimination.
Addition to double bonds: electrophilic addition of water, hydrogen halides, Hydrogenation.
Alcohols, thioalcohols, ethers, thioethers: Nomenclature. Physical properties, Acidity and basicity. The S-S bond.
Carbonyl group: Oxidation and Reduction in Organic Chemistry. Aldehydes and Ketones. Nucleophilic addition reactions to the carbonyl group. Keto-enolic tautomerism. Enolates. Aldol condensation.
Carboxylic Acids and derivatives: classification. Acidity. Physical properties. Acyl halides. Organic acid anhydride. Esters. Amides. Nitriles. Synthesis and reactivity.
Aromatic and heterocyclic compounds: benzene, benzene derivatives and main heterocyclic compounds. Resonance and electronic structure.
Electrophilic aromatic substitutio. Effects of substituent groups in the electrophilic aromatic substitution. Acidity of phenols.
Amines: Properties as bases. Reactivity as nucleophiles
Carbohydrates: Monosaccharides, disaccharides and polysaccharides. Aldoses and ketoses. D and L series. Mutarotation. Glycosides.
Aminoacids: Acidity and basicity.L and D series. Peptide bond. Peptide synthesis. Proteins.
Lipids: Saturated and unsaturated fatty acids. Triglycerides. Soaps
Nucleic acids: Nucleosides, nucleotides and nucleic acids
Organic Compounds of biological interest: Purines and pyrimidines.
Laboratory experience:
Introduction. Purification, distillation and crystallization techniques.
Separation techniques. Extraction at variable pH
Chromatography. Stationary and mobile phase. Silica gel chromatography: Tlc and column chromatography. Principles and applications
Examples of organic reactions
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Practicals: 16 hours
Lessons: 56 hours
Lessons: 56 hours
Professor:
Pagliarin Roberto