Unit ORGANIC CHEMISTRY 2
- Course
- Chemistry
- Study-unit Code
- 55055612
- Curriculum
- In all curricula
- Teacher
- Luigi Vaccaro
- CFU
- 12
- Course Regulation
- Coorte 2017
- Offered
- 2019/20
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa integrata
ORGANIC CHEMISTRY 2
| Code | 55044106 |
|---|---|
| CFU | 6 |
| Teacher | Luigi Vaccaro |
| 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 | Summary of the fundamental concepts of the Organic Chemistry illustrated in the course of Organic Chemistry I Acidity of the organic compounds and related reactivity Rearrangment reactions Synthesis and reactivity of ethers Reactivity of carbonyl compounds Introduction to the chemistry of sulfur, phosphorus and silicon chemistry Heterocyclic compounds Polymers Spectroscopy in Organic Chemistry Synthetic methodology |
| Reference texts | Peter C Vollhardt, Neil E Schore, Organic Chemistry 7th American edition 2016 |
| Educational objectives | This course completes the teaching of Organic Chemistry program that is given to students of the degree course in Chemistry. It aims to complete the acquisition of the fundamental knowledge of the subject. In particular with this course the student is introduced to the chemistry of conjugated compounds, heterocyclic compounds, and deepens the stereochemical concepts affecting the organic chemistry. |
| Prerequisites | Organic Chemistry I |
| Teaching methods | This course completes the Organic Chemistry program that is given to the students in the Chemistry degree course. It aims to complete the acquisition of the basic arguments for a good knowledge of the subject. Particularly with this course, the student is introduced to the chemistry of conjugate compounds, transposition reactions, retrospectives, protection of functional groups and deepen the stereochemical notions affecting organic chemistry. The course should allow the student to acquire the following basic knowledge: Know the principles of reactivity that trigger a transposition process Understand the basic protection / deprotection methods of a functional group Understand the basic methods of using organic compounds containing sulfur Understand the basic methods of using organic compounds containing Phosphorus Know the fundamental chemistry that allows the synthesis of Wittig and its variants based on carbanions of different chemical nature |
| Other information | |
| Learning verification modality | The proof of profit includes the assessment of written reports on laboratory activities and an oral test, which will involve the formulation of 4-5 questions over a period of approximately 40 minutes. The test is aimed at assessing students' abilities and assessing the environmental impact of a chemical process and distinguishing the various factors that influence it. The overall evaluation of the exam 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%, 20%, 20%. |
| Extended program | Summary of the fundamental concepts of the Organic Chemistry illustrated in the course of Organic Chemistry I Stereochemistry, Reactions and Mechanism, Addition and addition-elimination reactions, Functional group chemistry and classes of organic compounds. Acidity of the organic compounds and related reactivity Acidity of hydrogen atoms alpha to carbonyl, nitrile and nitro groups, keto-enol tautomerism, reactivity of enols, alpha halogenation of carbonyl compounds. Enolate ion formation and reactivity, alkylation of enolate ions, decarboxylation, the use of ethyl acetoacetate and malonic esters in synthesis. Enolate acylation, carbonyl condensation reactions, aldol reaction and analogues, the Claisen condensation and related reactions. The Cannizzaro reaction Rearrangment reactions Carbocation rearrangements (Wagner-Meerwein, pinacol), Beckmann, Baeyer-Villiger, Hofrnann and Curtius rearrangements. Synthesis and reactivity of ethers Williamson ether synthesis, acidic cleavage, cyc1ic ethers and crown ethers. Synthesis and ring opening reactions of epoxides. Reactivity of carbonyl compounds Stereochemistry of addition reactions to carbonyls. Conjugate addition to unsaturated carbonyl systems (Michael addition). Introduction to the chemistry of sulfur, phosphorus and silicon chemistry Thiols and sulfides, sulfoxides and sulfones. Structure, nomenc1ature, preparation and reactions of simple organophosphorous and organosilicon compounds. The Wittig and Wadsworth-Emmons reactions, Peterson olefin. Heterocyclic compounds Pyrrole, furan, thiophen, pyridine, aromaticity in monocyclic heterocyclic compounds, electrophilic and nucleophilic attack, oxidation and reduction, acid/base properties. Polymers Free radical and ionic polymerisation of alkenes (addition or chain growth). Step-growth (condensation) polymerisation. Spectroscopy in Organic Chemistry Spectroscopy and mass spectrometry for structure determination Infrared (IR) spectroscopy, characteristic group frequencies. Ultraviolet (UV) and visible spectra, colour and conjugation. Nuclear magnetic resonance (NM) spectroscopy, chemical equivalence, the delta scal chemical shift. lH NMR spectra, integration, proton counting, spin-spin coupling, the n+ l rule. 13C NMR spectroscopy, multiplicity in off-resonance spectra. Mass spectra, molecular ions, accurate mass, isotope signals, and simple fragmentations. Synthetic methodology Systematic approaches to the design of syntheses, utilisation of reactions of functional groups for synthesis, functional group interconversions and the formation of carbon-carbon and carbon-heteroatom bonds, application and removal of protecting groups, analysis and modification of synthetic sequences. Use of retrosynthetic analysis and the disconnection approach, synthons and corresponding reagents. |
ORGANIC CHEMISTRY LABORATORY 2
| Code | 55044206 |
|---|---|
| CFU | 6 |
| Teacher | Stefano Santoro |
| 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 | Principles of infrared spectroscopy; characteristic absorbance of functional groups. NMR spectroscopy: theoretical basis, chemical shift, splitting and coupling constants, factors influencing chemical shifts and coupling constants, first-order spectra. Laboratory experiences are dedicated to the synthesis, purification and characterization of organic molecules. |
| Reference texts | Slide handouts provided, in electronic form, to all the attendants. "Guida Pratica alla Interpretazione di Spettri NMR", A. Randazzo; Loghia, 2018. "Identificazione Spettrometrica di Composti Organici", R. M. Silverstein, F. X. Webster, D. J. Kiemple, D. L. Bryce; Casa Editrice Ambrosiana (CEA), 2016. "Advanced Practical Organic Chemistry", J. Leonard, B. Lygo, G. Procter; CRC Press, 2013. |
| Educational objectives | The course provides a part of lectures and an experimental part in the laboratory. The first part aims at introducing two spectroscopic techniques: infrared spectroscopy (IR) and the proton nuclear magnetic resonance spectroscopy (1H-NMR). The experimental part is focused on organic synthesis and on the application of spectroscopic knowledge to verify the structures of products and intermediates prepared in the laboratory. The main aim of this course is to provide students with the fundamental knowledge to analyze and interpret the IR and NMR spectra of simple organic compounds. At the end of the course, the student should be able to identify the structure of an unknown organic compound on the basis of its IR and 1H-NMR spectra and limited chemical information. Main knowledge acquired will be: - Knowledge of normal vibration modes of a polyatomic molecule; - Knowledge of main vibration modes of common functional groups; - Knowledge of the most significant stretching bands of the main functional groups for their recognition; - Basic knowledge of nuclei that are able to give the phenomenon of nuclear magnetic resonance; - Essential knowledge of the nuclear resonance phenomenon; - Knowledge of the meaning of magnetic and chemical equivalence; - Knowledge of chemical shift (d) and spin-spin coupling constant (J); - Knowledge of factors that influence the value of the chemical shift and the value of the spin-spin coupling constant; - Knowledge of the meaning of integration signal; - Knowledge of first-order coupling patterns and ability to distinguish first-order couplings from higher-order couplings; - Essential knowledge about multistep synthetic sequences, processing procedures of a reaction mixture, and methods for the characterization of the reaction products. The main competence (i.e. the ability to apply acquired knowledge) will be: - Identify from IR spectrum analysis the presence of the most significant functional groups, such as the carbonyl and the hydroxyl group; - Be able, with the aid of correlation tables, to detect the normal vibrations of the functional groups present in the molecular structure; - Recognize in a 1H-NMR spectrum the presence of magnetically different protons; - Predict the chemical shifts of the various types of protons present in a molecule; - Recognize the various spin coupling and discern a first order spin system from those of higher order; - Apply the IR and NMR knowledge to determine the complete structure of an organic molecule; - Be able to design and implement a synthesis of an organic compound. |
| Prerequisites | In order to be able to understand the topics of the course you must have successfully passed the Chimica Organica 1 and Chimica Generale ed Inorganica 1 exams. |
| Teaching methods | The Laboratory module of Organic Chemistry 2 presents both a part of lectures and a practical part in the laboratory. The course is organized as follows: - Lectures of two hours each, held in the classroom, aimed at introducing two spectroscopic techniques: IR and 1H-NMR. During the lectures exercises for the interpretation of infrared and NMR spectra will be held. Attendance to these lessons is highly recommended. - Laboratory activity is focused on the preparation of organic compounds in one or more synthetic steps, and on the subsequent purification and physico-chemical and spectroscopic characterization through the techniques mentioned above. The laboratory activity involves 8 sessions lasting 5 hours (14:30 to 19:30). Depending on the number of students, generally two groups of maximum of 24 students are necessary. The frequency to the laboratory is mandatory in view of the fact that many experiences are closely connected. In fact, the product of a reaction may be the reagent of a second reaction and some syntheses require more synthetic steps, which occupy more than one day. |
| Other information | - |
| Learning verification modality | The exam consists in a written test and an oral test. The written test requires providing the solution to practical exercises and answering theoretical questions, and will require no more than two hours. The test is designed to evaluate the ability to apply theoretical knowledge to solve problems, the ability to understand the proposed problems and the ability to communicate in written form. The oral test consists in an interview of about 40 minutes aiming at the assessment of the level of knowledge and ability of understanding reached by the student on the theoretical and methodological contents as indicated in the program. The oral test will also test the student communication skills and his ability in organizing the exposure of the theoretical topics. |
| Extended program | Infrared spectroscopy (IR). General concepts. Biatomic molecule as a harmonic oscillator. Basic equations. Anharmonic behavior. Physical meaning of the force constant. Absorption of infrared radiation. Polyatomic molecules. Vibrational degrees of freedom. Main bands of stretching and bending. Secondary bands of overtone and coupling. Group frequencies. General methods of sample preparation. Review of diagnostic and features frequency for identification of principal functional groups. Examination of IR spectra of: alkanes, alkenes, alkynes, aromatics, alcohols, phenols, ethers, ketones, aldehydes, carboxylic acids and acyl derivatives, nitriles and amines. Analysis of inductive and mesomeric effects on absorption bands. Effect of ring size of cyclic compounds. Solvent effect and inter-and intramolecular hydrogen bond on absorption bands of various functional groups. Interpretation of IR spectra of organic molecules of medium structural complexity. Proton Nuclear Magnetic Resonance Spectroscopy (1H NMR). Introduction. Magnetic properties of atomic nuclei. Physical principle of magnetic resonance. Instrumentation. The chemical shift and the shielding constant. Inductive, anisotropic, steric, solvent and hydrogen bonding effects on the chemical shift. Spin-spin coupling constant. First order spectra. AXn, AmXn and AMX spin systems. Spectra of non-first order. AB and ABX spin systems. Chemical and magnetic equivalence. Simplification of complex spectra using deuterium. The coupling constant: geminal, vicinal and long range coupling. Factors affecting the coupling constant. Examples of interpretation of 1H NMR spectra of organic molecules of medium structural complexity. EXPERIMENTAL PART Consists of 7-8 practical experiences involving the preparation of organic molecules in single or multistep syntheses and the characterization of the products through the above mentioned spectroscopic techniques. |