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Subject: ORGANIC CHEMISTRY II (A.A. 2024/2025)

degree course in CHEMISTRY

Course year 2
CFU 9
Teaching units Unit Chimica organica II
Organic Chemistry and Biochemistry (lesson)
  • TAF: Compulsory subjects, characteristic of the class SSD: CHIM/06 CFU: 4
Organic Chemistry and Biochemistry (exercise)
  • TAF: Compulsory subjects, characteristic of the class SSD: CHIM/06 CFU: 2
Organic Chemistry and Biochemistry (laboratory)
  • TAF: Compulsory subjects, characteristic of the class SSD: CHIM/06 CFU: 3
Teachers: Adele MUCCI, Alessio NICOLINI
Exam type oral
Evaluation final vote
Teaching language Italiano
Contents download pdf download

Teachers

Adele MUCCI
Alessio NICOLINI

Overview

The purpose of the course is to give the base knowledge for the understanding of the chemistry of polyfunctional and heterocyclic compounds, the execution of simple organic syntheses safely, the identification and characterization of the synthesized products, as well as to promote the ability of making judgements, of correctly communicate the results and the acquisition of learning skills inherent to the subject.
For a more complete understanding of the training objectives, please refer to the reading of the learning outcomes expected following the completion of this course.

Admission requirements

Good knowledge of the theories of chemical bond and structure of organic compounds.
Good knowledge of stereoisomerism and of stereochemistry.
Good knowledge of physical and chemical properties of monofunctional organic compounds (all the contents of Organic Chemistry I course)

Course contents

Theory, 32 h, 4 CFU:

1 CFU (8 hours) polyenes and their reactivity
1.2 and 1.4 additions, kinetic and thermodynamic aspects, Diels-Alder and hints on other pericyclic reactions, auto-oxidation of fatty acids, natural derivatives of isoprene and hints to their biosynthesis, neoprene.
Double bonds activated by electron withdrawing groups
conjugate addition reactions, reactions with organometallic reagents, reduction with hydrides, Michael reaction, Robinson annulation, Mannich reaction to obtain the precursors.

1.25 CFU (10 hours) carbohydrates:
monosaccharides and stereoisomery, mutarotation, reactions of monosaccharides (formation of glycosides, ethers, esters, acetals, oxidation with metaperiodate, oxidation to aldonic acids, aldarici, alduronici, reduction to formation of osazoni, Kiliani-Fischer synthesis, degradation of Wohl and Ruff, Fischer demonstration of the structure of glucose.
Disaccharides, starch and main cellulose derivatives.

1.5 CFU (12 hours) heterocyclic compounds
furan, pyrrole, thiophene. synthesis (Paal-Knorr and Knorr) and synthesis of 1,4-dicarbonyl precursors. reactivity: differences in reactivity in electrophilic heteroaromatic substitutions (halogenation, acylation, nitration, sulfonation, Mannich and Vilsmeier). reactions to the nitrogen of pyrrole, hydrolysis and Diels-Alder reaction of furan, nucleophilic substitutions on thiophene. outline of polymerization reactions.
pyridine. Hantzsch synthesis. reactivity: electrophilic and nucleophilic substitutions (including Chichibabin reaction). reactivity of hydroxypyridine/pyridones, pyridine N-oxide and pyridinium salts.

0.25 CFU (2 hours) hints on lipids and amino acids.

2 CFU (20 h) interpretation of IR and 1H NMR spectra of organic compounds (plus 10 h tutored by a graduate student).

1 CFU (10 h) IR spectroscopy with exercises
modes of vibration. Notes on the instrumentation. Characteristic and diagnostic absorptions of alkanes, alkenes, alkynes, nitriles, aromatics, ketones, aldehydes, esters, amides, amines and ammonium salts, anhydrides, acyl chlorides, sulfur compounds, halogenates and nitro derivatives.
0.6 CFU (6 h) 1H NMR spectroscopy with exercises
Outline of principles and instrumental aspects. Chemical shift. Coupling constants and spin systems of the first and second order.
0.4 CFU (4h) Exercises in preparation of NMR + IR exam

3 CFU (36 h)bLaboratory practice:

0.5 CFU (6 h) Behavior in the organic chemistry laboratory and procedures for the proper use of the laboratory equipment, to ensure safety in the laboratory in general and, in particular, in the experiences to be carried out, including disposal;
2.5 CFU (30 h) 8 laboratory experiences
1. Oxidation of cyclohexanol to cyclohexanone with commercial bleach
2. Synthesis of 1-bromobutane
3. Synthesis of 1-iodobutane
4. Synthesis of t-pentyl chloride + recording of IR spectra at LADAC
5. Reduction of acetophenone with sodium borohydride
6. Hydrolysis of the methyl ester of salicylic acid
7. Protection of a ketone as 1,3-dioxolane
8. Claisen-Schmidt condensation

Teaching methods

The teaching is delivered through lectures, which are carried out at the blackboard and with the aid of audiovisual media (Power Point presentations), classroom exercises on the spectroscopy part and laboratory practice, carried out in the lab, working in small groups. For the theory part, the teaching material consists of one of the recommended organic chemistry texts and it is strongly recommended that students take notes. Attendance to face-to-face lectures, classroom exercises and laboratory practices, although strongly recommended, is not compulsory. The frequency to less than 75% of the laboratory practice sessions, if not adequately justified, will result in the evaluation of 0/30 for each laboratory session skipped beyond the first two. Attendance at practical laboratory exercises is verified by direct appeal by those present. The course is delivered in Italian Lessons in streaming and video-recorded, if required by the pandemic

Assessment methods

The exams will take place at the end of the course, according to the official exam calendar published on the ESSE3 platform. The student can always register via the ESSE3 platform. The exam (both the written and the oral parts) can be taken only after having passed that of Organic Chemistry 1.To enroll in the oral exam, you must have passed the written exam. The three modules are evaluated in thirtieths with weight proportional to CFUs of each module. -evaluation in at the end of the course of the laboratory activities, this is based on the results of mandatory tests administered individually before each experience (80% of the assessment), on the laboratory notebook (report of the experiences and elaboration of the experimental data obtained, including spectroscopic data) (15%) and of the student behavior during practice (warning received for not using IPD or other misbehavior) (5%). The frequency to less than 75% of the laboratory practice sessions, if not adequately justified, will result in the evaluation of 0/30 for each laboratory session skipped beyond the first two. Attendance at practical laboratory exercises is verified by direct appeal by those present. -assessment of the spectroscopy module: it is based on a written examination during which the student identifies a simple organic molecule starting from the raw formula, IR and 1D 1H NMR spectra (80%), and shows to have a basic theoretical knowledge of the key topics (basic factors determining the position of IR and 1H NMR signals and the 1H NMR signal shape) (20%). - Oral examination: three questions, maximum one hour, during which the understanding of the topics covered in the class, the ability to predict the outcome of a reaction starting from given reagents or the reagents needed to prepare a product (90%) and the use of a correct language and graphic symbolism (10%) will be evaluated. KNOWLEDGE, UNDERSTANDING and ABILITY TO APPLY KNOWLEDGE AND UNDERSTANDING are evaluated in all three modules. JUDGING AUTONOMY and COMMUNICATION SKILLS and are evaluated during written and oral examinations. ABILITY TO LEARN is assessed by the degree of self-depth reached by the student in the discussion of the topics of oral and written exams. Laude is given to students who achieve a final evaluation of 30/30 and pass brilliantly the oral examination (without any help from the teacher).

Learning outcomes

Knowledge and understanding: Through lectures and exercises done with the teacher, the students learn the basics of organic chemistry related to the synthesis and reactivity of the systems covered in the course, the basis for performing safely simple organic synthesis in the laboratory and to test the structure and purity of prodoti obtained.
Applying knowledge and understanding: Through lectures, practical laboratory and exercises done in autonomy, the students are able to apply their knowledge to solve problems related to the synthesis and reactivity of organic molecules, to identify simple organic molecules and to conduct safely laboratory activities under teacher supervision.
Making judgments: through lectures, exercises and drills conducted in a controlled manner, students acquire the ability to critically interpret data on molecular properties and connected with the reactivity of functional groups.
Communication skills: the frequency to the lessons and students involvement during these allow them to develop the ability to use the specific language of the subject, to present the data obtained in a concise way, to express the concepts learned with a proper language and symbology.
Learning skills: the activities described allow the student to acquire the methodological tools for
continue their studies and to face more specialized courses.

Readings

J. Gorzynski Smith, Chimica Organica, Mc Graw Hill, 2007

P. Yurkanis Bruice, Chimica Organica, EdiSES, 2004

William H. Brown, Christopher S. Foote,Brent L. Iverson, "Chimica Organica", III Ed., EdiSES, Napoli, 2006.

Seyhan Ege, "Chimica Organica - Struttura e reattività", II Ed., IDELSON-GNOCCHI, 2003

R. M. Roberts, J. C. Gilbert, S. F. Martin Chimica Organica Sperimentale, Ed. Zanichelli 1999

L. M. Harwood, V. J. Moody, J. M. Percy, Experimental Organic Chemistry Standard and Microscale, 2nd edition, Blackwell Science 1999
Sulla pagina del portale moodle relativa all’insegnamento sono disponibili già all'inizio del corso (e nel rispetto dei diritti d’autore)
- le dispense utilizzate dal docente per i moduli di laboratorio e di spettroscopia.
- Le schede descrittive delle esperienze di pratiche di laboratorio
- Raccolte di esercizi IR, NMR, NMR+IR da svolgere


On the page of the moodle portal relating to this course, they are available at the beginning of the course (and in compliance with copyright)
- the handouts used by the teacher for the laboratory and spectroscopy modules.
- The descriptive cards of the experiences of laboratory practices
- Collections of IR, NMR, NMR + IR exercises to be performed