Unit ORGANIC CHEMISTRY I
- Course
- Chemistry and technology of drugs
- Study-unit Code
- 65005209
- Location
- PERUGIA
- Curriculum
- In all curricula
- Teacher
- Francesca Marini
- Teachers
-
- Francesca Marini
- Luana Bagnoli
- Hours
- 72 ore - Francesca Marini
- 14 ore - Luana Bagnoli
- CFU
- 9
- Course Regulation
- Coorte 2021
- Offered
- 2022/23
- Learning activities
- Base
- Area
- Discipline chimiche
- Academic discipline
- CHIM/06
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa monodisciplinare
- Language of instruction
- Italian
- Contents
- Structure, IUPAC nomenclature, synthesis and typical reactivity of the main classes of organic compounds. Basic organic stereochemistry. Mechanisms of the most common reactions for the inter-conversion of functional groups.
- Reference texts
- Lecture slides.
P. Y. BRUICE, Organic Chemistry, Pearson.T. W. G. SOLOMONS, C. B. FRYHLE Organic Chemistry, Wiley.
W. H. BROWN, C. S. FOOTE, B. L. IVERSON, E. V. ANSLYN Organic Chemistry, Cengage Learning.
M. V. D'Auria, O. Tagliatela Scafati, A. Zampella Guida ragionata allo svolgimento di esercizi di Chimica Organica, Loghia. - Educational objectives
- The aim of this teaching is to provide the basic knowledge for understanding and describing the structure and reactivity of the main classes of organic compounds. At the end of the course students will be expected to have acquired the following skills:
-to represent the electronic, structural and stereochemical features of organic molecules,
-to assign IUPAC names,
-to understand and predict the reactivity of organic molecules according to the functional groups.
-to apply the acquired concepts and notions in solving problems and exercises,
-to provide plausible plan for the synthesis of simple organic compounds. - Prerequisites
- In order to understand and know how to apply the contents of the course you must have passed the examination of General and Inorganic Chemistry
- Teaching methods
- The course is organized in lectures (6 hours a week) for a total of 72 hours and exercise sessions (approximately 2 hours a week) during which questions and exercises will be proposed and discussed. Exercise sessions have the aim of encouraging active participation by the students, facilitating and improving the understanding of the basic principles and concepts of organic chemistry, and developing the ability to apply acquired knowledge for problem solving .
- Other information
- The attendance is strongly recommended.
- Learning verification modality
- Written and oral exam. The global exam will assess: (a) the acquisition of basic nomenclature and symbolisms of organic chemistry, (b) the understanding of the chemistry of the main functional groups, (c) the ability to write plausible reaction mechanisms, (d) the ability to effectively communicate, rework and apply the studied principles and concepts, (e) problem solving ability, (f) ability to propose synthetic procedures of simple organic molecules. The written exam consists in two open questions related to the multi-step synthesis of simple organic compounds using the synthetic methodologies discussed in the course.
The oral exam (approximatively 45 minutes), starts from the discussion of the written exam and continues probing the knowledge of topics covered in the course such as the stereochemistry, the reactivity of the main functional groups, and the mechanisms of the main organic reactions. The oral exam will also verify the student's communication skills.
For information about support services for students with disabilities and / or DSA visit the page http://www.unipg.it/disabilita-e-dsa - Extended program
- Electronic Structure and Bonding. Functional groups and main class of organic compounds. IUPAC nomenclature. Organic reactions . Reaction coordinate diagrams. Reaction intermediates. Alkanes and cycloalkanes. Halogenation of alkanes. Radicals: structure and stability. Stereochemistry and the arrangement of atoms in space. Conformation: torsional strain and angle strain. Newman projections. Chirality. Asymmetric Carbons and stereocenters. Absolute configuration. Stereodescriptors R/S. Cahn-Ingold-Prelog rules. Optical properties and specific rotation. Enantiomeric excess. Racemates. Racemic resolutions. Correlations of configuration. Compounds with more than one stereocenters. Three-dimensional representation of molecules. Solid or dashed wedged bonds formulas and Fisher projections. Enantiomers and diastereoisomers. Meso compounds. Relative configuration. Stereocenters different from carbon. Atropoisomery: allenes and biaryls. Prochiral molecules. Enantiotopic and diastereotopic hydrogens. Cis/Trans isomers. E/Z stereodescriptors. Alkenes. Electrophilic addition reactions. Addition of hydrogen halides or water to alkenes. Carbocations: formation, structure and stability. Carbocation rearrangements. Regioselectivity. Addition of HBr in the presence of peroxides. Addition of halogens. Formation of halohydrins. Oxymercuration/Reduction. Hydrogenation Reactions . Hydroboration/Oxidation. Addition of peroxyacids to alkenes. Hydroxylation reactions by KMnO4 and OsO4. Stereochemistry of the addition reactions to alkenes. Stereoselective and stereospecific reactions. Allylic halogenation. Stability of the allylic radical. Electronic delocalization and resonance. Dienes. Reactivity of conjugated dienes: 1,2 or 1,4-additions. Thermodynamic vs kinetic control. Alkynes. Addition reactions to alkynes. Addition of water and keto-enol tautomerism. Reductive reactions. Acidity of hydrogens of terminal alkynes. Alkyl halides. Aliphatic nucleophilic substitutions. SN1 and SN2 mechanisms: kinetic and stereochemical considerations. Competition between SN2 and SN1 reactions. Solvation effects: polar aprotic solvents. Elimination reactions of alkyl halides. E2 and E1 mechanisms. Competition between substitution and elimination. Organolithium and organomagnesium compounds. Grignard reagents for the preparation of alcohols and carboxylic acids. Alcohols and ethers. Conversions of alcohols into alkyl halides: reaction of alcohols with hydrogen halides, phosphorus halides and thionyl chloride. SNi. Conversions of alcohols into sulfonate esters. Dehydration of alcohols. Formation of alkoxides and Williamson etherification. Oxidation of primary and secondary alcohols. Epoxides. Aromatic compounds. Benzene: structure and stability. Aromaticity. Huckel’s rules. Polycyclic benzenoid hydrocarbons. Aromatic heterocyclic compounds. Aromatic ions. The general mechanism for the electrophilic aromatic substitution. Nitration, sulfonation, halogenation, Friedel-Crafts acylation and alkylation of benzene. Electrophilic aromatic substitutions on substituted benzenes: the effect of substituents on reactivity and orientation. Inductive and resonance effects. Activating and de-activating groups. Examples of electrophilic aromatic substitutions on naphtalene and heteroaromatic compounds. Halogenation of alkylbenzenes. Benzylic radical. Oxidation of alkylbenzenes. Phenols. Aromatic halides: nucleophilic aromatic substitution. Carboxylic acids and their acidity. Carboxylic acid derivatives: acyl halides, acid anhydrides, esters, amides and preparation. General mechanism of the nucleophilic acyl substitution reaction. Relative reactivities of carboxylic acids and carboxylic acid derivatives. Inter-conversion of carboxylic acid derivatives. Acid-catalyzed ester hydrolysis. Acid catalyzed hydrolysis of esters. Saponification. Trans-esterification. Reductions of carboxylic acids and of their derivatives. Hofmann and Curtius rearrangements. Dicarboxylic Acids and Their Derivatives. Aldehydes and ketones. Nucleophilic additions to carbonyl compounds: reactions with hydride ion, alcohols (protecting groups), ammonia and ammonia derivatives (imines formation), hydrogen cyanide. Wittig reaction. Relative reactivity of carbonyl compounds. Carbonyl compounds reactions at the alpha-carbon. Acidity of alpha-hydrogens. Keto-enol tautomerism. Enolates. Halogenation of the alpha-carbon of aldehydes and ketones. Hell-Volhard-Zelinsky reaction.Aldol reaction, mixed aldol reaction and related reactions. Perkin and Henry reactions. Reformatsky reaction. Claisen condensation and mixed Claisen condensation. Dieckmann reaction. Polifunctional compounds Beta dicarbonyl compounds and their acidities. Keto-enol tautomerism in beta dicarbonyl compounds. The malonic ester synthesis. Decarboxylation of 3-oxocarboxylic acids. Acetoacetic ester synthesis. Alpha,beta-unsaturated carbonyl compounds. Michael reactions. Amines. Basicity. Synthesis of alkyl and aromatic amines. Gabriel synthesis. Reaction of the amines with nitrous acid: the diazonium salts. Sandmayer reactions. Diazocopulation and azo compounds. Multi-step syntheses of simple organic compounds. Practice problems and exercises.