AIMS AND CONTENT

LEARNING OUTCOMES

Acquire the fundamental concepts that allow to understand the structure and reactivity of the main classes of organic compounds, with particular emphasis on the biologically important reactions. Acquire a basic knowledge of the main primary metabolites. To be able to execute some of the typical practical procedures of an organic chemistry laboratory. To be able to work in group and to write a laboratory report.

AIMS AND LEARNING OUTCOMES

Knowledge and understanding

Provide the fundamental concepts that allow to understand the structure and reactivity of the main classes of organic compounds, with particular emphasis on the biologically important reactions.

Provide the instruments to acquire a basic knowledge of the main primary metabolites; to be able to execute some of the typical practical procedures of an organic chemistry laboratory; to be able to work in group; to write a laboratory report.

Skills and abilities

Students have to be able to: know and understand the structures of the main organic compounds; know how to write the structural formulas of organic substances correctly; recognize the molecular diversity based on the chemical structures (isomerism); know the main organic reactions; predict the products of a given reaction by evaluating the kinetic and thermodynamic aspects; know and understand the main primary metabolites (carbohydrates, proteins, lipids, nucleic acids); know how to perform the common purification techniques of organic compounds; carry out some reactions of basic organic chemistry; use some analytical tools for the characterization of organic compounds; write correctly a laboratory report; to work in team.

PREREQUISITES

The fundamental concepts of general chemistry acquired during the course of General Chemistry in the first semester

TEACHING METHODS

Traditional lessons in the classroom (52 hours). The solutions of problems will be treated in additional and optional tutoring hours (10). Laboratory sessions (7 sessions of 4 hours each).

The attendance is compulsory. Students must attend all laboratory sessions and 60% of the classroom lessons.

SYLLABUS/CONTENT

1. Introduction and unfunctionalised compounds (6 hours). 1.1 Introduction. 1.2 The chemical bond in organic compounds. 1.3 Alkanes
2. Survey of the main functional groups: physical and acid-base properties. Purification/separation techniques (8 hours). 2.1 Survey of the main functional groups and elements of nomenclature. 2.2 Non-bonding interactions and physical properties. 2.3 Acid-base properties of organic compounds. 2.4 Separation through extraction. 2.5 Crystallization. 2.6 Distillation. 2.7 Chromatography.
3. Stereochemistry (6 hours). 3.1 Conformations. 3.2 Types of stereoisomers, chirality, R/S notations. 3.3 Compounds with two stereogenic carbons. 3.4 Polarimetry. 3.5 Enantiomeric mixtures. 3.6 Equivalent stereogenic centres. 3.7 Chemical and biological properties of enantiomers. 3.8 Classical resolution through diastereomeric salts. 3.9 E/Z isomety in alkenes.
4. Reactions of C=C double bonds (5 hours). 4.1 Thermodynamic and kinetic aspects of reactions. 4.2 Alkene hydrogenation. 4.3 Electrophilic addition to C=C double bond, Markovnikov rule. 4.4 Benzene and aromaticity. 4.5 Heteroaromatic compounds and their basic properties. 4.6 Electrophilic substitution on benzene. 4.7 Keto-enol tautomerism in carbonyl compounds, phenols and heteroaromatic compounds.
5. Reactions of C=O double bonds (7 hours). 5.1 Nucleophilic additions to carbonyl compounds. 5.2 Acyl nucleophilic substitution. 5.3 Other carboxylic derivatives. 5.4 Acyl nucleophilic substitution in biology. 5.5 Reactions of carbon nucleophiles at the α positions of carbonyl.
6. Redox reactions of the main organic compounds (chemical and biological) (6 hours). 6.1 Determination of oxidation number. 6.2 Oxidation and reduction of oxygenated organic compounds. 6.3 Alkene oxidations. 6.4 Quinones. 6.5 Redox reaction at N or S.
7. Aminoacids and peptides (2 hours)
8. Carbohydrates (4 hours). 9.1 Structure and stereochemistry of main monosaccharides. 9.2 Mutarotation. 9.3 Glicosides. 9.4 Monosaccharide oxidations and reductions. 9.5 Polysaccharides.
9. Lipides (1 hours). 10.1 Triglycerides - soaps - waxes. 10.2 Phospholipides.
10. Nucleic acids (1 hours)
11. Radical reactions (2 hours)
12. Exercises (five 2 hour sessions)(optional; extra-CFU): exercises on programme subjects.
13. Laboratory: seven 4 hour sessions.

RECOMMENDED READING/BIBLIOGRAPHY

1. Slides of lessons (published on aula web)
2. Exercises and solutions (published on aula web)
3. W. H. Brown, "Introduzione alla Chimica Organica", EdiSES
4. J. McMurry "Fondamenti di Chimica Organica", Zanichelli
5. B. Botta "Chimica Organica Essenziale", EDI-Ermes.
6. J.G. Smith "Fondamenti di Chimica Organica", McGraw Hill
7. L.G. Wade "Fondamenti di Chimica Organica", Piccin
8. D. Klein, "Fondamenti di Chimica Organica", Pearson
9. P. Y. Bruice, «Elementi di Chimica Organica», EdiSES

TEACHERS AND EXAM BOARD

Exam Board

LUCA BANFI (President)

LISA MONI (President)

ANDREA BASSO

SAMANTHA CAPUTO

CHIARA LAMBRUSCHINI

CINZIA TAVANI

LESSONS

LESSONS START

March 2, 2020

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

To access to the exam, the student must have first delivered the laboratory report (one each couple). After the correction and th evaluation, the professor will provide the student (through aulaweb) a copy eventual corrections and observations.

The exam will be oral. Exam topics will be requested exclusively, as shown in the slides provided on the aulaweb.

Students must book at least 48 hours in advance on https://servizionline.unige.it/studenti/esami/prenotazione.

Generally the exam includes 3 questions. The first will be general and will cover one of the classes of chemical reactions described in the central part of the course. The second will concern the laboratory (not only what has been done practically in the laboratory but also on the theory connected to it). The third will cover the primary metabolites. The exam usually lasts 45 minutes.
 

ASSESSMENT METHODS

The laboratory report will be evaluated taking into consideration the following parameters: use the appropriate language and specific vocabulary, using correct schemes and formula. The report is complete in all its parts, including description of procedures, fenomena observed, mathematical calculations and conclusions

The ability to work in groups will be assessed on the basis of observation by the professor during laboratory sessions.

The exam is oral and is always conducted by the two professors at least 30 minutes (typically 45 minutes). With these methods, the commission is able to verify with high accuracy the achievement of the lerneanig outcomes. When these are not reached, the student is invited to deepen the study and to make use of further explanations from the teachers.

The student will have to demonstrate, writing on the blackboard, the achievement of the lerneanig outcomes and writing correctly formulas, stoichiometric equations, reaction mechanisms.

Exam schedule