Unit ORGANIC CHEMISTRY 1
- Course
- Chemistry
- Study-unit Code
- 55010115
- Curriculum
- In all curricula
- Teacher
- Oriana Piermatti
- CFU
- 15
- Course Regulation
- Coorte 2023
- Offered
- 2024/25
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa integrata
ORGANIC CHEMISTRY 1
| Code | 55143108 |
|---|---|
| CFU | 8 |
| Teacher | Oriana Piermatti |
| Teachers |
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| Hours |
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| Learning activities | Base |
| Area | Discipline chimiche |
| Academic discipline | CHIM/06 |
| Type of study-unit | Obbligatorio (Required) |
| Language of instruction | Italian |
| Contents | The structure of organic molecules, nomenclature, isomerism. Relationship between structure, reactivity and chemical-physical properties. Stereochemistry of organic compounds. Synthesis and reactivity of the main classes of organic compounds. Mechanisms of the main organic reactions. |
| Reference texts | 1. W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote – “Chimica Organica” – EdiSES, VII ed.; 2. J. McMurry – “Chimica Organica”- Piccin, IX Ed.; 3. P. Y. Bruice- “Chimica Organica” – EdiSES, III Ed. 4. M. V. D’Auria, O. T. Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, Loghia; 5. Teacher lectures. |
| Educational objectives | The aim of this teaching is to provide students with the basic knowledge for understand and describe the structure and reactivity of the main classes of organic compounds, which are fundamental for tackling more advanced chemistry courses. At the end of the course students are expected to have acquired the following skills: - Represent the electronic, structural and stereochemical characteristics of organic molecules; - Assign the IUPAC name to an organic molecule of medium structural complexity starting from its structure and vice versa, including stereochemical notations; - Understand and predict the chemistry of organic molecules based on the functional groups present in the molecular structure; - Qualitatively predict some chemical-physical properties of organic molecules; - Establish the order of acidity and basicity of different organic molecules; - Propose synthetic routes for the preparation of organic compounds of simple structure. |
| Prerequisites | To understand and apply the topics of the course, is required a good knowledge of the basic concepts of general chemistry about the atomic structure, chemical bonding, acidity and alkalinity, equilibrium constants. These concepts will be revisited in the first lessons of the course for those who have not yet taken the exam in General and Inorganic Chemistry. |
| Teaching methods | The course is organized into lectures (6 hours per week) for a total of 56 hours, along with classroom exercises during which questions and exercises will be proposed and discussed. The classroom exercises, conducted in parallel with the lectures, aim to encourage the active participation of students, facilitate and improve the understanding of the fundamental principles and concepts of organic chemistry, and develop the ability to apply the acquired knowledge to solve problems. |
| Other information | Slides of the lectures, in pdf format, will be provided by the teacher. Available on UniStudium. Attendance is highly recommended. |
| Learning verification modality | The exam consists of two parts: 1. Written exam for admission to the oral exam - 10 questions with open answer - duration of the exam 2 hours. The exam is considered passed with a score of at least 18/30. During the course, two partial written exams will be scheduled, which can replace the total written exam if both outcomes are positive. 2. Oral exam: The oral exam consists of a discussion of about 40 minutes aimed at assessing the level of knowledge achieved by the student. The oral exam starts from the discussion of the written exam and will continue by exploring the knowledge of topics such as the stereochemistry, the reactivity of major functional groups, and the mechanisms of major organic reactions. The student must demonstrate a basic theoretical knowledge of organic chemistry and familiarity with its terminology and formalism, understanding of the chemistry of major functional groups, ability to formulate reaction mechanisms, and capability to propose synthetic procedures for structurally simple molecules. The overall evaluation of the exam will consider not only the student's ability to apply and connect acquired knowledge, but also their deduction and synthetic skills, and communication skills. In formulating the final grade, the assessment of the Laboratory module of Organic Chemistry 1 will also be considered, which will take into account the results of experiments and the behavior of the student in the laboratory. The exam will allow verifying the achievement of the expected educational objectives in relation to the professional training of the chemist. Students with disabilities and/or DSA (Specific Learning Desorders) are invited to visit the page dedicated to compensatory tools and dispensatory measures and to get in touch in advance with the teacher to evaluate the most suitable instruments |
| Extended program | Electronic structure, hybridization, and chemical bond. Bond polarity. Formal charge and resonance. Acids and bases. Functional groups and main classes of organic compounds. Types of organic reactions. Electrophilic and nucleophilic sites. Energy/reaction coordinate diagrams. Reaction intermediates: carbocations, carbanions, and radicals. Alkanes. IUPAC nomenclature. Isomerism. Radical halogenation. Structure and stability of radicals. Stereochemistry and the arrangement of atoms in space. Conformation: torsional strain, angle strain, and steric strain. Newman projections. Cycloalkanes: stability, conformation and cis-trans isomerism. Conformations of cyclohexane, axial and equatorial bonds. Stereochemistry: Chirality. Stereocenters. Enantiomers. Absolute configuration. R/S configuration descriptors, Cahn-Ingold-Prelog rules. Optical activity and specific rotation. Enantiomeric excess. Racemic mixtures. Resolution of racemic mixtures. Three-dimensional representation of molecular structures. Solid and dashed wedge bonds and Fischer projections. Compounds with multiple chiral centers: enantiomers and diastereoisomers. Meso compounds. Relative configuration. Compounds with stereocenters other than carbon. Prochiral molecules. Homotopic, enantiotopic, and diastereotopic hydrogens. Alkenes: Structure and preparation. Geometric isomerism. E,Z nomenclature. Electrophilic addition reactions to alkenes. Addition of hydrogen halides and water. Carbocations: formation, structure, and stability. Transpositions. Markovnikov's rule. Regioselectivity. Addition of HBr: peroxide effect. Addition of halogens. Formation of halohydrins. Oxymercuration/reduction. Hydrogenation reaction. Hydroboration-oxidation. Addition of peroxyacids and ozone to alkenes. Hydroxylation reactions. Stereochemistry of addition reactions to alkenes. Stereoselective and stereospecific reactions. Allylic halogenation. Stability of allylic radicals. Electron delocalization and resonance. Dienes. Reactivity of conjugated dienes: 1,2 or 1,4 additions. Kinetic vs thermodynamic control. Alkynes: Structure and preparation. Addition reactions to alkynes. Addition of water and keto-enol tautomerism. Hydrogenation of alkynes. Acidity of terminal alkynes and acetylide ions. Aromatic compounds. Benzene: structure and stability. Concept of aromaticity. Huckel's rule. Polycyclic aromatic hydrocarbons. Aromatic ions. Aromatic heterocyclic compounds: pyridine and pyrrole. Mechanism of electrophilic aromatic substitution reactions. Nitration, sulfonation, halogenation, Friedel-Crafts alkylation, and acylation reactions. Effect of substituents on reactivity and orientation. Inductive and resonance effects. Activating and deactivating groups. Examples of electrophilic substitution on naphthalene and main heteroaromatic compounds. Radical halogenation of the side chain of alkylbenzenes. Benzylic radical. Oxidation of alkylbenzenes. Alkyl halides. Preparations. Aliphatic Nucleophilic Substitution reactions. SN1 and SN2 mechanisms: kinetics and stereochemistry. Competition between SN1 and SN2. Solvent effect: polar aprotic solvents. Beta-elimination reactions. Dehydrohalogenation. E2 and E1 mechanisms. Competition between substitution and elimination. Organolithium and organomagnesium reagents. Grignard reagents in the formation of new C-C bonds. Aryl halides: nucleophilic aromatic substitution reactions. Alcohols: Physical properties. Types of alcohols. Alcohol acidity. Preparation. Conversion of alcohols to alkyl halides: reaction with hydrogen halides, phosphorus halides, and thionyl chloride. Dehydration and oxidation reactions. Transformation of alcohols into sulfonic esters. Formation of alkoxides. Phenols. Acidic properties compared to alcohols. Ethers and epoxides. Williamson ether synthesis. Epoxide synthesis. Acid- and base-catalyzed epoxide opening. Thiols and sulfides. Aldehydes and ketones: Structure and properties. Preparation. Nucleophilic additions to the carbonyl group. Relative reactivity of carbonyl compounds. Addition of water, alcohols, nitrogen derivatives, hydrogen cyanide, hydride ions, and Grignard reagents. Reactivity of carbonyl compounds at the alpha carbon. Acidity of alpha hydrogens. Keto-enol tautomerism. Enolate ions. Reactions via enol or enolate ion. Base- and acid-catalyzed halogenation of ketones. Aldol condensation. Related condensation reactions. Carboxylic acids: Acidity of carboxylic acids. Comparison of acidity with other functional groups. Effect of substituents on acidity. Nitriles: reactions. Functional derivatives of carboxylic acids: acyl chlorides, anhydrides, esters, and amides and their preparation. Nucleophilic acyl substitution reaction: general mechanism. Relative reactivity of acyl derivatives. Interconversion of acyl derivatives. Esterification reaction. Acidic and basic hydrolysis of esters. Transesterification reaction. Reduction of carboxylic acids and their derivatives. Claisen condensation. 1,3-Dicarbonyl compounds and their acidity. Keto-enol tautomerism in 1,3-dicarbonyl compounds. Malonic synthesis of carboxylic acids. Acetoacetic synthesis of ketones. Amines: Structure and properties. Basicity. Comparison with amides. Synthesis of aliphatic and aromatic amines. Gabriel synthesis of primary amines. Quaternary ammonium salts. Reactions of amines with nitrous acid. Diazonium salts and their use in organic synthesis. Sandmeyer reactions. Diazocopulation reaction and azo compounds. |
| Obiettivi Agenda 2030 per lo sviluppo sostenibile | The course aims to provide quality, equitable and inclusive education as a basis for improving people's lives and achieving sustainable development. |
ORGANIC CHEMISTRY LABORATORY 1
| Code | 55143107 |
|---|---|
| CFU | 7 |
| Teacher | Laura Goracci |
| Teachers |
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| Hours |
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| Learning activities | Caratterizzante |
| Area | Discipline chimiche organiche e biochimiche |
| Academic discipline | CHIM/06 |
| Type of study-unit | Obbligatorio (Required) |
| Language of instruction | Italian |
| Contents | The main purpose of the course is to provide the student with basic knowledge of laboratory techniques and methodologies that will allow him to work in an organic chemistry laboratory in complete self-sufficiency and in full respect of safety standards for its safeguarding and that of others. |
| Reference texts | Students can choose one of the following reference texts: R.M. ROBERTS, J.C. GILBERT, S.M. MARTIN, Chimica Organica Sperimentale, Ed. Zanichelli. M. D'ISCHIA, La Chimica Organica in Laboratorio, (Tomo I e II) Ed. Piccin. D.L. Pavia, G.M. Lampman, G.S. Kriz, Il Laboratorio di Chimica Organica, Ed. Sorbona, Milano. A.I. Vogel, Chimica Organica Pratica, II Ed., Casa Editrice Ambrosiana, Milano. |
| Educational objectives | The Module of Organic Chemistry Laboratory 1 provides a part of frontal lessons concerning the separation and purification techniques of organic compounds and a laboratory part where students will put the learned knowledge directly into practice. At the end of the course, each student should be able to prepare an organic compound of simple structural complexity, know how to separate it from the reaction mixture and purify it appropriately according to its physical and chemical characteristics. The main acquisitions will be: Know the main equipment and materials that are essential for proper laboratory activity. Know the basics for the correct assembling of laboratory glassware. Know the operation and use of small laboratory equipment. Know the technical basics and methodologies for separating and purifying organic compounds based on their chemical-physical characteristics. Know the basics of distillation processes. Know the basic aspects of chromatographic techniques. Know the main chemical recognition tests for the most common functional groups. The main skills (i.e. the ability to apply acquired knowledge) will be: Being able to handle, in a completely autonomous way, the assembly and use of a common laboratory equipment. Have the ability to choose and use the best technique for separating a product from the reaction mixture. Be able to choose the solvent or the solvent mixture best suited to crystallize a solid substance. Be able to select a solvent or a mixture of solvents to make a TLC or column chromatography. To be able to design and implement a synthesis of an organic compound of simple structural complexity. Always be able to evaluate the potential risks arising from the use of chemicals. |
| Prerequisites | Prerequisites It would be desirable for the student to attend and pass the first year course exams profitably. In order to follow the best and learn the contents of the course, the student must possess the following knowledge; Knowledge of phase changes and significance of the phase diagram; Knowledge of stoichiometric calculations. Knowledge of concentration units; This knowledge is a basic prerequisite for the student who intends to follow the module with profit. |
| Teaching methods | The course is organized as follows: - Two-hour front lectures, held in the classroom, address the basic contents of the various separation purification techniques for organic compounds and all related aspects. During lessons, whenever possible, materials and equipment will be used to help you learn. The frequency of these lessons is highly recommended. -The laboratory activity focuses on the preparation of organic compounds and subsequent separation and purification and chemical-physical characterization. The laboratory activity involves 6-8 experiences. The afternoon laboratory activity lasts 5 hours (14.30-19.30), depending on the number of students there are usually two rounds with a maximum number of students 24 per round. The frequency of the Laboratory is compulsory also considering that many experiences are closely linked to each other. - At the end of frontal lessons and laboratory activity, a collegial simulation (2h) of the exam is made. |
| Other information | The files (pdf), used by the teacher for lessons in the classroom, will be available to all students who take the course. |
| Learning verification modality | As regards the theoretical part, the final learning test will be unique with the Organic Chemistry 1 course, with two open-ended questions for the laboratory part included in the written test. As regards laboratory experiences, the student will have to provide a short report on a word template provided by the teacher in which the results obtained will be inserted. Students with disabilities and/or DSA are invited to visit the page dedicated to the tools and measures envisaged and to agree in advance what is necessary with the teacher (https://www.unipg.it/disabilita-e-dsa ). |
| Extended program | The course is structured in two parts: frontal or theoretical lesson and one of practical laboratory. Arguments of the theoretical part. Prevention and Safety in a organic chemistry laboratory. Glassware and laboratory equipment. Types and characteristics of laboratory glass. Assembling glassware. Separation and purification techniques and methodologies. Filtration techniques: by gravity and vacuum. Liquid-liquid extraction processes: simple and selective. Continuous liquid-solid extraction (Soxhlet). Methods of purification of solid substances: crystallization, sublimation and centrifugation. Determination of the melting point as a purity method for solid compounds. Drying agents. Methods for the removal of reaction water. Drying of solvents and liquid substances. Liquid compound purification: simple and fractional distillation at atmospheric pressure and under vacuum, steam distillation. Adsorption and distribution chromatography. Chromatographic separation techniques: thin film chromatography (TLC) and column chromatography (CC). The eluents, and detection methods for TLC. Contents about instrumental chromatographic techniques: glc and HPLC. Laboratory experiences 6-8 experiences regarding synthesis, separation, purification and characterization of organic compounds and recognition assays of some functional groups will be performed. Each student will work individually. |
| Obiettivi Agenda 2030 per lo sviluppo sostenibile |