Unit ORGANIC CHEMISTRY 1
- Course
- Chemistry
- Study-unit Code
- 55010115
- Curriculum
- In all curricula
- Teacher
- Raimondo Germani
- CFU
- 15
- Course Regulation
- Coorte 2020
- Offered
- 2021/22
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa integrata
ORGANIC CHEMISTRY 1
| Code | 55143108 |
|---|---|
| CFU | 8 |
| Teacher | Raimondo Germani |
| Teachers |
|
| Hours |
|
| Learning activities | Base |
| Area | Discipline chimiche |
| Academic discipline | CHIM/06 |
| Type of study-unit | Obbligatorio (Required) |
| Language of instruction | Italian |
| Contents | Organic Chemistry is often perceived by the students as a series of concepts to be acquired by memory. The aim of this course is to provide a method of reasoning to acquire the necessary basic knowledge to facilitate learning. In this regard we will be provided numerous examples of practical application of the concepts taught, along with controls aimed at assessing the level of learning. Particular attention will be given to the relationship between chemical structure, reactivity and physical properties. General topics: structure, and IUPAC nomenclature of the main organic compounds. Synthesis reactions and chemical behavior of the main functional groups of organic compounds. Basic concepts of the stereochemistry of organic compounds. Main mechanisms of organic reactions. |
| Reference texts | Students will be able to use and / or consult the following texts: W. H. BROWN, B. L. IVERSON, E. V. ANSLYN, C. S. FOOTE, Chimica Organica; Ed. Edises, Napoli, VI ed. 2019. Guida alla soluzione dei problemi da «chimica organica» di Brown, Iverson, Anslyn, Foote; Ed. Edises IV ed. 2016. |
| Educational objectives | The aim of the Organic Chemistry 1 course is to provide the student with the main basic knowledge for understanding and describing the structure and reactivity of the main classes of organic compounds. The student, who has continuously followed the course and the various classroom exercises, should have acquired the following skills: Knowing how to represent the electronic, structural and stereochemical characteristics of organic molecules; Be able to assign the IUPAC name to an organic molecule of medium structural complexity; Be able to recognize if a molecule has stereoisomers; Understanding and predicting the chemism of organic molecules on the basis of the functional groups present in the molecular structure; Be able to qualitatively predict some chemical-physical properties of molecules; Be able to establish the order of acidity and basicity of different organic molecules; Be able to hypothesize synthetic pathways for organic compounds of simple structure. |
| Prerequisites | In order for the student to be able to understand and know how to apply the contents of the course, he must have passed the exam in General and Inorganic Chemistry. |
| Teaching methods | The Organic Chemistry 1 course is organized in lectures (6 hours per week) for a total of 56 hours, during which questions and exercises will also be proposed and discussed. During the course, some lessons will be dedicated exclusively to exercises. The classroom exercises are intended to facilitate and improve the understanding of the fundamental principles and concepts of the discipline and develop the ability to apply the acquired knowledge for problem solving. At the end of the lectures there will be a collective simulation of the exam. |
| Other information | Slides of the lectures, in pdf format, will be provided by the teacher. Available directly on UniStudium. Attendance is highly recommended |
| Learning verification modality | Oral examination. The oral exam, lasting approximately 45 minutes, aims to assess the student's ability to connect and apply the knowledge learned during the course and individual study. The student will have to demonstrate to have the basic theoretical knowledge of organic chemistry and to know its terminology and formalism, to understand the chemism of the main functional groups, to formulate the reaction mechanisms, and to be able to propose synthesis procedures of structurally simple molecules. The overall assessment of the exam will take into account not only the student's ability to apply and connect the knowledge acquired and answer the questions correctly, but also his ability to deduce, synthesize and mastery of the terms used. In the formulation of the final grade, the judgment regarding the Laboratory module in Organic Chemistry 1 will also be considered, which will take into account the results of the experiences and the behavior held by the student in the laboratory. |
| Extended program | Electronic structure, hybridization and chemical bond. Functional groups and main classes of organic compounds. IUPAC nomenclature. Types of organic reactions. Electrophilic and nucleophilic sites. Energy / coordinate reaction diagrams. Reaction intermediates: carbocations, carbanions and radicals. Alkanes. Isomerism. Radical halogenation. Structure and stability of radicals. Stereochemistry and arrangement of atoms in space. Conformation: torsional strain, angular strain and steric strain. Newman projections. Cycloalkanes. Conformations and cis-trans isomerism of cycloalkanes, axial and equatorial bonds in cyclohexane, conformations of cyclohexane. Alkenes: electronic structure. Geometric isomerism. Nomenclature E, Z. Alkenes preparation. Electrophilic addition reactions to alkenes. Addition of water, halogens and hydrogen halides. Carbocations: formation, structure and stability. Transpositions. Markovnikov's rule Regioselectivity. Addition of HBr: effect of peroxides. Formation of halohydrins. Oxymercuration / reduction. Addition of hydrogen. Hydroboration-oxidation. Addition of peroxyacids and ozone to alkenes. Hydroxylation reactions with KMnO4. Stereochemistry of addition reactions to alkenes. Stereoselective and stereospecific reactions. Allyl halogenation. Stability of the allyl radical. Electronic delocation 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. Reductions. Acidity of terminal alkynes and acetylide ions. Stereoisomerism. Stereocenters. Absolute configuration. R/S configuration descriptors, Cahn-Ingold-Prelog rules. Chiral molecules. Optical activity and specific rotatory optical power. Enantiomeric excess. Racemic mixtures. Resolution of racemic mixtures. Three-dimensional representation of molecular structures. Full and dashed wedges and Fischer projections. Enantiomers and diastereomers. Meso compounds. Relative configuration. Prochiral molecules. Homotopic, enantiotopic and diastereotopic hydrogens. Alkyl halides. Preparations. Aliphatic Nucleophilic Substitution Reactions. SN1 and SN2 mechanisms: kinetics and stereochemistry. Competition between SN1 and SN2. Solvent effect: dipolar aprotic solvents. Beta-elimination reactions. Dehydrohalogenation. E2 and E1 mechanisms. Competition between substitution and elimination. Grignard’s reagents in the formation of alcohols and carboxylic acids. Alcohols. Types of alcohols. Dehydration and oxidation reactions. Conversion of alcohols into alkyl halides: reaction with halogenhydric acids, phosphorus halides and thionyl chloride. Transformation of alcohols into sulphonic esters. Alcohol acidity. Alkoxide formation. Ethers and Epoxides. Williamson’s ether synthesis. Epoxides synthesis. Epoxides opening by acid and base catalysis. Aromatic compounds. Benzene: structure and stability. Concept of aromaticity. Huckel's rule. Polycyclic aromatic hydrocarbons. Ionic aromatic compounds. Monocyclic heteroaromatic compounds with 5 and 6 members: pyrrole, furan and pyridine. Mechanism of the aromatic electrophilic substitution reaction. Nitration, sulfonation, halogenation, Friedel-Crafts alkylation and acylation reactions. Substituent effects on reactivity and orientation. Inductive and mesomeric effect. Activating and deactivating groups. Examples of electrophilic substitution on naphthalene and on the main heteroaromatic compounds. Free radical halogenation of the alkylbenzenes side chain. Benzyl radical. Oxidation of alkylbenzenes. Aryl halides: aromatic nucleophilic substitution reactions. Phenols: structure and chimism. Acid properties and comparison with alcohols. Aldehydes and ketones: structure and properties of the carbonyl group. Carbonyl group synthesis. Nucleophilic additions to the carbonyl group: addition of hydride ion, alcohols, nitrogen derivatives, hydrogen cyanide and Grignard reagents. Carbonyl addition-elimination reactions. Relative reactivity of carbonyl compounds. Reactivity of carbonyl compounds at 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. Aldol-like condensations. Carboxylic acids: structure. Acidity of carboxylic acids. pKa values. Effect of substituents on acidity. Acidity comparison with other functional groups. Functional derivatives of carboxylic acids: acyl chlorides, anhydrides, esters and amides and their preparation. Mechanism of the nucleophilic acyl substitution reaction. Reactivity scale of acyl compounds. Interconversion of acyl derivatives. Esterification reactions. Basic and acid esters hydrolysis. Transesterification reaction. Reduction of carboxylic acids and its derivatives. Nitriles: reactions. Claisen condensation. 1,3-dicarbonyl compounds and their acidity. Keto-enol tautomerism in 1,3-dicarbonyl compounds. Malonic synthesis. Acetoacetic synthesis. Amines: primary, secondary and tertiary. Basicity of nitrogen compounds. Synthesis of aliphatic and aromatic amines. Gabriel's synthesis of primary amines. Quaternary ammonium salts. Reactions of amines with nitrous acid. The diazonium salts: their use in organic synthesis. Sandmayer reactions. Reaction of diazocopulation and azo compounds. |
ORGANIC CHEMISTRY LABORATORY 1
| Code | 55143107 |
|---|---|
| CFU | 7 |
| Teacher | Raimondo Germani |
| Teachers |
|
| 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 | The module of Organic Chemistry Laboratory 1 only provides for oral examination, which consists in answering 3-4 questions. The test is aimed at assessing the students' ability to use and link the knowledge acquired on the separation and purification techniques of organic compounds to real cases, and on the chemical tests for the recognition of functional groups. The overall assessment of the exam will take into account, besides the student's ability to apply and link the knowledge gained and answer the questions correctly, including its ability to deduct, synthesize and master the terms used. In the formulation of the final judgment, laboratory practice activity, that is, the results of experience and laboratory behavior will contribute 50%, 30% will be determined by the correctness of the answers, and 20% is related to the language property shown during the test. |
| 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. |