67062 - Organic Chemistry with Laboratory

Learning outcomes

The course will give students a knowledge of organic chemistry basic elements, i.e. organic compounds nomenclature, structure, and classification; structure and reactivity of the main organic functional groups; structural-, regio-, and stereo-isomerism; structure and reactivity of the most important reactive intermediates; fundamental organic reactions mechanisms (e.g. electrophilic and nucleophilic substitution [both aliphatic and aromatic], additions, eliminations, nucleophilic addition and acyl substitution to carbonyl groups). It will also furnish basic information on how to work properly and safely in a laboratory of organic chemistry. Particular attention will be paid to safety rules, usage of the most common apparatuses, and standard procedures of preparation, purification, and characterisation of organic compounds, as well as bibliographic resources and databases.

Course contents

Reminder of general chemistry. The organic compounds. Electronic effects of functional groups.
Conformational isomers of ethane, substituted ethanes, and cyclohexanes. Configurational isomers (enantiomers, diastereoisomers, R/S absolute configuration, cis/trans isomers in disubstituted cycloalkanes). 
The mechanisms of organic reactions. Kinetics, transition states and intermediates. Activation energy and reaction energy.

ALKANES. Natural sources and reactions. Mechanism of halogenation.

ALKENES. cis/trans (E/Z) isomers. Dienes and polyenes. Preparation methods and reactions (electrophilic addition, reduction, oxidation, radical addition). Reactions of conjugated dienes.

ALKYNES. Acidity. Preparation methods and reactions (formation of salts, hydrogenation, electrophilic addition).

ARENES (aromatic hydrocarbons). Aromaticity. Benzene. Polynuclear and heteronuclear aromatics. Ortho, meta, and para positions in benzene. Sources of aromatics. Reactivity (electrophilic aromatic substitution in benzene and monosubstituted benzenes, nucleophilic aromatic substitution, oxidation).

HALOGEN DERIVATIVES. Preparation methods of alkyl and aryl halides. Reactivity of alkyl halides (reactions with metals, SN1 and SN2 nucleophilic substitutions, E1 and E2 eliminations). Reactions of aryl halides.

ALCOHOLS AND PHENOLS. Preparation methods of alcohols, phenols, and diols. Reactivity.

ETHERS, EPOXIDES, THIOLS, AND SULFIDES. Preparation methods and reactivity.

AMINES. Preparation methods and reactivity. Diatotization of aromatic amines: reactivity of diazonium salts.

Structure and reactivity of the CARBONYL GROUP. Nucleophilic addition and acyl substitution reactions.

ALDEHYDES AND KETONES. Preparation methods and reactivity. 

CARBOXYLIC ACIDS AND DERIVATIVES (ACYL HALIDES, ANHYDRIDES, ESTERS, AMIDES, NITRILES). Acidity of carboxylic acids. Preparation methods and reactivity of carboxylic acids and their derivatives.

ENOLATES. Reactivity of enolates of aldehydes and ketones (keto-enolic tautomerism, aldolic condensation). Reactivity of ester enolates (Claisen condensation). Reactivity of beta-ketoester enolates (acetacetic synthesis). Reactivity of beta-diester enolates (malonic synthesis).

Safety in a laboratory of organic chemistry: products, apparatuses, standard procedures, waste disposal, common hazards, safe working practice, and emergency procedures.

Laboratory equipments and procedures: glassware, filtration devices, heating mantles and plates, stirring methods, vacuum pumps, rotary evaporators, equipment assembly, the laboratory notebook.

Base procedures in a laboratory of organic chemistry: distillation, extraction, crystallisation, thin-layer- and column-chromatography.

Characterisation by spectral analysis: infrared spectroscopy, mass spectrometry, NMR spectroscopy.

Examples of synthesis, separation, purification, and characterisation of organic compounds (examples of simple reactions) with measurement of physical constants.

The chemical literature: the structure of chemical information and literature, Chemical Abstracts and Beilstein, on-line databases and resources.

Readings/Bibliography

J. McMurry, Fondamenti di Chimica Organica, IV Ed. Italiana, Zanichelli, 2011

J. McMurry, Chimica Organica, VII Ed. Italiana, Piccin, 2008

P. Yurkanis Bruice, Chimica Organica, II Ed. Italiana, EdiSES, 2012

P. C. Montevecchi, M. L. Navacchia, La Chimica Organica, Aracne Editrice

W. Brown, T. Poon, Introduzione alla Chimica Organica, IV Ed., EdiSES, 2011

Chimica Organica (a cura di B. Botta), edi-ermes, 2011

D'Auria, Taglialatela Scafati, Zampella, Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica, Loghia Editrice

R. M. Roberts, J. C. Gilbert, S. F. Martin, Chimica Organica Sperimentale, Zanichelli, Bologna, 1998

H. Hart, L. E. Craine, Laboratorio di Chimica Organica, Zanichelli, Bologna, 1998

D. C. Eaton, Laboratory Investigations in Organic Chemistry, McGraw-Hill, 1988

J. Leonard, B. Lygo, G. Procter, Advanced Practical Organic Chemistry, Blackie Academic & Professional (Chapman & Hall), II Ed., London, 1995

W. R. Moore, A. Winston, Laboratory Manual for Organic Chemistry: a Microscale Approach, McGraw-Hill, New York, 1996

Teaching methods

Lessons supported by PowerPoint presentations, exercises, and practical activity in the laboratory (introduction during the lectures) performed by the students under the supervision of the teacher. The teacher is willing to receive students outside the lesson time for additional explanations and/or discussion.

Assessment methods

Final written assessment followed by oral exam.

As the experimental Lab course is an essential part of the whole exam, attendance of the practical activity in the laboratory is compulsory: only absences due to exceptional, acceptable reasons will be justified. During the laboratory activity the students should keep a laboratory notebook containing the detailed description of each experiment and the theoretical rationalisation of every experimental observation. Based on the notebook content, the students could be asked to fill in appropriate work sheets where specific questions should be answered. Evaluation of the notebook will be part of the final mark and the notebook must be delivered to the teacher at least one week before the written exam. As an alternative, the students can deliver weekly the filled work sheets.

To deliver eilther the notebook or the sheets, in addition to attending Labs, is compulsory for admission to the final exam.

The final exam will be written, with an allowed time of ca. 3 hours. During the exam, using of books/notes is not permitted, but the students will be allowed to refer to correlation tables of spectroscopic data. The written exam will deal with exercises related to both the theoric Course and the Lab one. Only students passing the written exam will be admitted to the oral exam, dealing with a further test on the whole Course contents. The final mark will be given as a weighted average between the written exam, the oral one, and the Lab reports.

Teaching tools

PowerPoint presentations and written lectures (laboratory section only) by the teacher are available on-line.

Office hours

See the website of Daniele Nanni

See the website of Luca Bernardi