AIMS AND CONTENT

LEARNING OUTCOMES

Students will be provided with basic knowledge of organic chemistry and the reactivity of monofunctional compounds. Students will first learn how to write correct Lewis and Kekulé formulas, as well as fundamental concepts relating to chemical bonds, resonance, bases and organic acids, the diversity and shape of molecules (with particular emphasis on stereochemistry), the nomenclature of the various classes functional (including aromatic and heterocyclic derivatives). The main objective will be to introduce students to the main organic reactions (electrophilic and nucleophilic additions with double and triple C = C bonds and double C = O bonds, aromatic electrophilic substitutions, acyl, aliphatic and aromatic nucleophilic substitutions, bond formation reactions C-C and C = C, redox reactions, radical reactions) making them understand the synthetic applications and the thermodynamic, kinetic and experimental problems.

PREREQUISITES

The fundamental concepts of General Chemistry acquired during the course of General and Inorganic Chemistry in the first semester

TEACHING METHODS

Traditional lessons in the classroom (64 hours). The solutions of problems will be treated in additional and optional tutoring hours. The attendance is not compulsory but, for statistical means, it wil be anyway monitored.

SYLLABUS/CONTENT

• Introduction to organic chemistry
  • Chemodiversity in organic chemistry. Lewis formulas. Representation of molecules. VSEPR theory. Molecular orbitals. Tridimensional structure.
  • Alkanes and cycloalkanes. Constitutional isomers
  • The concept of functional group
  • Survey of the main functional classes and basic systematic nomenclature
  • Physico-chemical properties of organic compounds
  • Acid-base properties (Bronsted) of organic compounds
  • Stereochemistry and conformational equilibria of organic molecules
  • Generality on organic reactions: names of main reactions, thermodynamical and kinetic aspects
• Electrophilic addition to C=C bonds
  • Generality and Markovnikov rule. Hammond postulate
  • Addition of hydrogen halides, water, halogens, boranes, formation of bromohydrins
  • Reactions of dienes and alkynes
• Aromatic compounds
  • benzene and aromaticity
  • aromatic electrophilic substitutions: halogenation, nitration, solfonation, Friedel-Crafts acylations and alkylations
  • steric and electronic effects of substituents. Orientation of electrophilic substitutions on monosubstituted benzenes.
  • Heteroaromatic compounds. Basic properties. Tautomeric equilibria. Electrophilic substitutions.
• The reactions of C=O bonds
  • Reversible nucleophilic additions to carbonyl compounds: gem-diols, acetals, imines
  • Generality of acylic nucleophilic substitutions
  • Preparation and hydrolysis of: acyl chlorides, anhydrides, esters, amides, nitriles
  • Acyl derivatives of other oxyacids: arbonic acid, sulphonic acids, nitric acid, sulphuric acid, phosphoric acid
• Redox reactions in organic chemistry
  • formal hydrogenations and dehydrogenations involving redox at C atom
    • hydrogenation of alkenes and alkynes
    • oxidation of oxygenated functionalities
    • reduction of oxygenated functionalities
    • reductive amination
  • other redox reactions at C atom
    • monooxygenation of hydrocarbons
    • epoxidation
    • dihydroxylation
    • ozonolysis
  • redox reactions involving N and S. Nomenclature and properties of sulphur derivatives.
  • oxidative additions of halides to metals: Grignard and organolithium reagents
• Formation of C-C bonds
  • Reactions of Grignard and organolithium reagents with carbonyl and acyl derivatives
  • Acidity at the alpha position: aldol and Claisen reactions
• Aliphatic Nucleophilic Substitutions
  • SN2 reactions: generality and application to th synthesis of ethers, amines, and to enolate alkylations
  • E2 elimination
  • SN reaction
  • E1 elimination
  • Reactivity of epoxides with nucleophiles
• Other reactions of aromatic compounds
  • aromatic nucleophilic substitution: SNAr mechanism, benzyne, SN1
  • Diazonium salts. Diazocopulation
• radical reactions
  • Generality
  • radical polymerization of ethylene and styrene
  • halogenation of alkanes
  • phenol synthesis via cumene hydroperoxide
  • auto-oxidation. Radical inhibitors
  • quinones and hydroquinones

RECOMMENDED READING/BIBLIOGRAPHY

The program will not follow a specific book.

Anyway, students are advised to integrate the lessons with consultation of any Organic Chemistry book for chemists (that can be borrowed in the library). For example:

• J. McMurry, CHIMICA ORGANICA, Piccin
• P.Y. Bruice, CHIMICA ORGANICA, EdiSES
• M. Loudon, CHIMICA ORGANICA, EdiSES
• P.C. Vollhardt, N.E. Schore, CHIMICA ORGANICA, Zanichelli
• A.A. vari, CHIMICA ORGANICA (a cura di B. Botta), Ediermes
• Brown-Foote-Yverson-Anslyn, CHIMICA ORGANICA, Edises

TEACHERS AND EXAM BOARD

Exam Board

ANDREA BASSO (President)

ALESSANDRO PELLIS

RENATA RIVA

LUCA BANFI (President Substitute)

CHIARA LAMBRUSCHINI (Substitute)

LISA MONI (Substitute)

CINZIA TAVANI (Substitute)

LESSONS

LESSONS START

see http://www.chimica.unige.it/didattica/orari_CTC  

Class schedule

ORGANIC CHEMISTRY

EXAMS

EXAM DESCRIPTION

The students who want to be submitted to the exam must registrate at least 48 hours in advance on https://servizionline.unige.it/studenti/esami/prenotazione

The exam will be essentially oral. However, it will be preceded, on the same day, by a written exam, whose aim is just to filter off the unprepared students in order to avoid useless loss of time for both sides. Therefore the written exam will not involve solution of problems, it will be relatively easy, and onlt these four outcomes will be communicated few hours after its end: excellent, good, sufficient and not sufficient. Only the students who have gained the first three grades will be admitted to the oral exam. The grade obtained during the written exam will not count for the final grade, apart from the fact that the maximum available grade for those judged "sufficient" will be 26. Even the students who have got "excellent" may eventually fail the oral exam.

The oral exam will involve 3 questions. The first one will be quite general. The second and third will be more specific. The relative weight of the three questions will be, approximately, 50%, 25%, 25%. When students who have got "excellent" in the wrtten exam, answers very well to the first question, the commission may decide to stop the exam (with a grade of 30) or to pose a more difficult question in order to judge if the student is worth the "cum laude".

During the oral exam the student must demonstrate to have reached the learning outcomes, both orally and (most importantly) writing formulas, chemical equations, mechanisms.
In case of students who have certified a "specific learning disease" (DSA) the commission may decide to go directly thrpough the oral exam where the student will be given enough time to understand the questions and answer to them. Requests of these aids must be presented not directly to the professor, but to the reference persons for DSA at the School of Science.

When the commission will judge that the learning oucomes have not been reached, the students willbe invited to repeat the exam in one of the subsequent dates.

When the commission have decided for a positive grade, the student may ask to refuse ot and repeat the exam. However the commission will decide whether to accept or not this refusal. In any case the request of refusal must be presented at once, and students are not allowed to change their minds later. If, later,the students repeats the exam and obtain an inferior grade, he/she can not ask to receive the grade that he/she had preiously refused.

ASSESSMENT METHODS

The oral exam is always carried out by two teachers with at least 5 years of experience and will last at least 30 minutes. In this way, taking into account also the preliminary written exam, the commission is definitely able to verify with high accuracy if the student has reached or not the learning outcomes.

During the oral exam the student must demonstrate to have reached the learning outcomes, both orally and (most importantly) writing formulas, chemical equations, mechanisms.

When the commission will judge that the learning oucomes have not been reached, the students willbe invited to repeat the exam in one of the subsequent dates.

Exam schedule

FURTHER INFORMATION

Only the students who have already successfully obtained the credits for "General Chemistry and Laboratory" will be admitted to the exam.