Unit ORGANIC CHEMISTRY 1
- Course
- Chemistry
- Study-unit Code
- 55010115
- Curriculum
- In all curricula
- Teacher
- Raimondo Germani
- CFU
- 15
- Course Regulation
- Coorte 2019
- Offered
- 2020/21
- 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 student 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 and physical properties, fulcrum of all the research in the field of physical organic chemistry. |
| Reference texts | K.Peter, C. Vollhardt, N.E.Schore- Chimica organica, Zanichelli ed. |
| Educational objectives | The main knowledge gained will be: • Basic knowledge of various types of homo- and heteronuclear chemical bonding; • Physical and chemical characteristics of the various functional groups; • knowledge of the fundamental reactions for the transformation of functional groups; • Basic knowledge of the different approaches to organic synthesis. The main skills will be: • ability to identify and classify organic molecules, and to transform them; • skill in the interpretation of the important molecular feature governing natural chemical processes; • skills in the recognition of the relathionships between molecular structure and properties |
| Prerequisites | In order to better understand the basic concepts of organic chemistry it is necessary to have successfully supported the General and Inorganic Chemistry Exam 1 with particular emphasis on structural chemistry. |
| Teaching methods | The course is organized as follows: - Lectures on all topics of the course - Classroom computer exercises |
| Learning verification modality | The exam consists of two written tests and an oral final examination. The written tests consist of the solution of open and closed pre-filled tests that refer to the various main contents of the course, in the number of twelve / fifteen tests for written test. The contents of the tests follow in chronological order those given during the theoretical lessons. The tests are articulated in a way to evaluate the learning of the fundamental concepts of the course, aimed at solving the problems posed. During the course, the teacher will provide numerous examples of the tests and their solutions. The oral test consists of an interview that focuses mainly on the issues insufficiently addressed in the written tests. In general, at least three questions will be asked to the candidate and the degree of understanding of the concepts, the deepening of the study, the appropriateness of the scientific language of exposure will be assessed. The exam evaluation will take into account the following aspects: correctness and adequacy of responses, processing skills and conceptual connection, mastery and language skills, according to the following percentages: 60%, 30%, 10%. |
| Extended program | Nomenclature IUPAC nomenclature for straight and branched chain hydrocarbons, monocyclic cycloalkanes, benzene and naphthalene, simple aromatic heterocyclic compounds, and their derivatives having any of the functional groups included in the organic chemistry core. SMILES representation of molecular structures. Sequence rules for specification of ligand priority, the E/Z designation, R/S to specify absolute configuration (Cahn, Ingold, Prelog).Stereochemistry Tetrahedral carbon, stereogenic (chiral) centres, chirality in molecules, geometrical and optical isomerism, optical activity, specific rotation, enantiomers, diastereomers, meso compounds, racemic mixtures and their separation. Conventions for representing three-dimensional chemical structures, conformations of ethane and butane, steric hindrance and preferred conformation. Conformation and cis-trans isomerism in cycloalkanes, axial and equatorial bonds in cyclohexane, conformational mobility of cyclohexane. The stereochemical requirements of substitution, addition, and elimination reactions.Reactions and Mechanism Types of organic reaction, reaction mechanisms, rates and equilibria, reaction coordinate energy diagrams, intermediates and transition states. Basic ideas of mechanism - electronegativity, polarisation, curly arrows, electrophiles and nucleophiles, reactive intermediates - carbocations, carbanions, free radicals. Acid-base catalysis.Substitution, addition and elimination reactionsGeneral mechanisms for SNl, SN2, SNAr, El, E2 and electrophilic aromatic substitution reactions, the influence of reagents and reaction conditions, the competition between nucleophilic substitution and elimination. Addition to carbon-carbon multiple bonds. Addition and addition-elimination reactions at carbonyl, imino and nitrile groups; esterification, hydrolysis and analogues.A1kylation and acylation of enols and enolates Acidity of hydrogen atoms alpha to carbonyl, nitrile and nitro groups, keto-enol tautomerism. Functional group chemistry and classes of organic compounds Alkanes: Sources, preparation, oxidation, free radical halogenation, combustion. Cycloalkanes - small, medium and large rings, ring strain.Alkenes: Electronic structure, cis-trans isomers, preparation via elimination reactions. Addition reactions - hydrogenation (including the Lindlar catalyst), electrophilic addition of HX, H20, halogens, orientation of alkene addition reactions, Markovnikov's rule, carbocation structure and stability, addition in the presence of peroxides - anti-Markovnikov. Hydroboration. Oxidation of alkenes by manganate(Vll), peroxo-acids, and ozone. Conjugated dienes, resonance, stability of allylic carbocations, 1,2- and 1,4- addition to dienes. Cycloaddition reactions (Diels-Alder). Alkynes: Structure and preparation. Electrophilic addition of H2, water, HX and X2, acidity, formation of alkyne anions, coupling reactions.Aromatic Compounds: Structure and stability of benzene, resonance, Huckel's ruIe, simple non-benzenoid aromatics (cyclopentadienyl, tropylium). Electrophilic aromatic substitution-halogenation, nitration, sulfonation, the Friedel- Crafts alkylation and acylation reactions. Isomerism of benzene derivatives, reactivity and orientation of reactions on substituted aromatic rings, oxidation and reduction of aromatic compounds. Side-chain halogenation, benzyl as a free radical, cation and anion. Naphthalene. Kinetic vs. thermodynamic control. Alkyl halides (haloalkanes and baloaromatic compounds): Preparation from alcohols, nucleophilic substitution reactions, elimination reactions, Grignard reagents. Haloaromatics and haloalkenes, their resistance to nucleophilic attack. Allylic bromination.Alcohols and phenols, ethers and epoxides: Primary, secondary and tertiary alcohols. Acidity of alcohols and phenols, hydrogen bonding. Synthesis of alcohols from alkenes and from carbonyl compounds. Reactions of alcohols - with hydrogen halides, phosphorus halides, dehydration, reaction with metals, acylation, oxidation.Amines and other nitrogen functions: Primary, secondary and tertiary amines, amine basicity, synthesis of amines by substitution and reduction reactions, reactions of amines - alkylation, Hofmann exhaustive methylation, acylation, preparation of diazonium compounds - and their use in synthesis; nitro compounds, ureas.Aldehydes and ketones: Structure and properties of the carbonyl group, synthesis of aldehydes and ketones, oxidation and reduction of aldehydes and ketones, nuc1eophilic addition of water, alcohols, amino compounds, and Grignard reagents.Carboxylic acids and derivatives: Structure, and properties of carboxylic acids, acidity, pKa values, the effect of substituents on acidity. Synthesis of carboxylic acids, nucleophilic acyl substitution reactions - esterification, acid halide and amide formation. Reactions of acid halides, acid anhydrides, esters, and amides - solvolysis, hydrogenolysis, reduction, reactions with Grignard reagents. Preparation and reactions of nitriles. |
ORGANIC CHEMISTRY LABORATORY 1
| Code | 55143107 |
|---|---|
| CFU | 7 |
| Teacher | Raimondo Germani |
| Teachers |
|
| Hours |
|
| 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. |
| 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. |