CHIMICA ORGANICA I E LABORATORIO

12 CFU - 2° Semester

Teaching Staff

VINCENZO CUNSOLO

Learning Objectives

Organic Chemistry and Lab I (Mod 1)
Aim of the course is to acquire the knowledge of the key concepts of the organic chemistry. In particular, the course is aimed:

- to introduce the fundamental knowledge for the study of the basic organic molecules in relation to its structure, reactivity, properties;

- to know the main classes of organic molecules;

- to the view of simple organic molecules in three dimensions with an emphasis to their stereochemical properties.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding: The students will have to demonstrate their mastery of basic knowledge about the organic chemistry. In particular, the students must show their ability to rationalize property-structure correlations of organic molecules

D2 - Ability to apply knowledge: The students will have to show knowledge and understanding of organic reactions required to produce synthetic processes of relatively complex molecules.

D3 - Autonomy of judgment: The students will have to apply their knowledge, understanding and skills. Particularly, the students must show his ability to critical reasoning and their ability to identify the most appropriate chemical reactions aimed to the synthesis of organic molecules.

D4 - Communication skills: The students must be able to communicate clearly with a correct property of language and terminological rigor their conclusions.

D5- Learning skills: The students will have to develop learning skills that will enable them to continue studying in a self-directed or autonomous way.
Course of Organic Chemistry and Lab I (Mod. 2)
The course will provide the students with the theoretical and practical knowledge of the main experimental techniques of the organic chemistry laboratory. Special emphasis will be given to safety-related issues. Moreover, the course content complements the theoretical concepts acquired in the Organic Chemistry I course.

The students will master a formally corrected scientific language. They will also be able to clearly express organic chemistry-related concepts and to write a scientific report.

At the end of the course, the students will be able to independently carry out the purification and characterization of an organic compound working in safe conditions.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding. The Students must have a complete knowledge of the equipment present in the Organic Chemistry laboratory and of standard laboratory procedures for the preparation and purification of organic compounds. Moreover, the students grow sensitivity to the risks involved in the laboratory techniques, how to use the individual safety devices and how to manage and dispose of glass devices and chemicals.

D2 - Ability to apply knowledge and understanding. The students will be able to apply the knowledge acquired during the course. In addition, they will be able to conduct practical experiments useful for the synthesis and extraction of organic molecules. They will have to be able to record and document their experimental activities in in the laboratory notebook.

D3 - Autonomy of judgment. The students must show independence of judgment in the interpretation of the experimental data and of the obtained results, as well as they must show ability to plan and conduct an experiment in organic synthesis employing methods explained and implemented experimentally during the course.

D4 - Communication skills. The students must be able to communicate clearly with a correct property of chemical language and terminological rigor, methods and issues concerning the preparation and purification of organic compounds.

D5 - Learning skills. The students will have to develop learning skills that will enable them to continuously update their knowledge useful to conduct practical experiments in successive chemistry lab courses.

Course Structure

Organic Chemistry and Lab I (Mod 1)
Classroom Lectures (35 hours)
Classroom Exercises (12 hours)

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus.

Learning assessment may also be carried out on line, should the conditions require it.
Course of Organic Chemistry and Lab I (Mod. 2)
The course consists of 6 credits corresponding to 72 hours divided between hours of theoretical lessons and hours of laboratory exercises. The hours of theoretical lessons are preliminary to the development of laboratory exercises. The student will be engaged in laboratory exercises lasting 4 hours each.

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus.

Learning assessment may also be carried out on line, should the conditions require it.

Detailed Course Content

Organic Chemistry and Lab I (Mod 1)
Introduction to carbon chemistry. Recalling the concepts of atomic orbitals. Electronic configuration of atoms. Representations of Lewis. The octet rule. The chemical bond. Covalent bonds and the Pauling electronegativity scale. Resonance theory. σ and π bonds. Hybrid orbitals sp3, sp2, sp. Intermolecular interactions. Classification of organic compounds and functional groups. General principles of the IUPAC nomenclature for organic compounds. Graphical representation of molecules.

Reactions in organic chemistry. Chemical bonds cleavage. Classification of carbon and hydrogen atoms in organic molecules. Carbocations, carbanions and alkyl radicals: geometry and stability. Reaction mechanisms, use of curly arrows for their representation. Energy diagrams. Recalling the concepts of acid and basic. Acid-basic reactions and redox reactions of organic compounds. Electrophiles and nucleophiles. Reaction classification: substitution, elimination and addition reactions. Regioselectivity, stereoselectivity, stereospecificity aspects of the reactions in organic chemistry.

Alkanes and cycloalkanes. IUPAC nomenclature. Source and importance of alkanes. Physical and chemical properties. Constitutional isomerism and conformational isomerism in alkanes. Cycloalkanes. Geometric isomerism of cycloalkanes. Reactivity: radical substitution and combustion reaction.

Constitutional isomers and stereoisomers. Constitutional isomerism. Stereoisomerism: conformational and configurational isomerism. Chirality. Asymmetric carbon. Enantiomers. Optical activity. Relative configuration and absolute configuration. Naming enantiomers: the R,S system of nomenclature. Three-dimensional representation of enantiomers. Stereoisomers with two or more asymmetric carbon atoms. Diasteroisomers and meso compounds. Biological importance of chirality. Separation of enantiomers. Geometric isomerism: cis-trans isomers.

Alkenes. Structure and nomenclature. Geometric isomers of alkenes: cis-trans and E-Z nomenclature. Physical properties. Alkenes in nature. Dienes, trienes and polyenes (hint). Electrophilic Addition reactions of conjugated dienes. Methods of preparation of alkenes. Carbon-carbon double bond reactivity: the electrophilic addition reaction in alkenes. The reaction mechanism. The addition of halogenidric acids and regioselectivity. Markovnikov's rule. The addition of water. Transposition of carbocations. The addition of halogens. Halohydrins. Oxidation of alkenes. Reduction of alkenes: catalytic hydrogenation. Cyclic alkenes.

Alkynes. Nomenclature. Triple bond structure. Reactivity. Acidity of a hydrogen bonded to an sp hybridized carbon. The addition reaction in alkynes. Addition of halogenidric acids and halogens. Reduction to alkenes (with Lindlar’s catalyst) and to alkanes.

Aromatic compounds. Structure and properties of benzene. Resonance energy and aromaticity concept. Hückel's rule. Nomenclature of mono-, di- and poly-substituted benzene derivatives. Reactivity of the benzene ring: the general mechanism for electrophilic aromatic substitution reactions. Halogenation; nitration; sulfonation; Friedel & Crafts alkylation, Friedel & Crafts acylation. Reaction of substituents on benzene. The effect of substituents on reactivity and orientation.

Alkyl and aryl halides. Structure and nomenclature. Preparation methods. Reactions of alkyl halides. Aliphatic nucleophilic substitution: the SN1 and SN2 mechanisms: role of substrate, leaving group, solvent and nucleophile. The elimination reaction (β-elimination): the mechanisms E1 and E2. The stereochemistry of substitution and elimination reactions. Competition between substitution and elimination reactions. Reaction with magnesium or lithium: formation of organometallic compounds. Grignard reagents.

Alcohols. Structure, nomenclature and classification of alcohols. Physical properties: the hydrogen bond. Preparation methods. Diols and glycols (hints). Alcohol group reactivity. Salt formation; acid and basic properties. Reaction with metals. Formation of alkyl halides: reactions with halogenidric acids (SN2 and SN1). Reaction with SOCl₂ and PBr₃. Alkenes formation: acid-catalyzed dehydration (E1 and E2). Regioselectivity and stereoselectivity. Oxidation of primary and secondary alcohols. Formation of semi-acetals and acetals. Ethers, epoxides, thiols and sulphides (hints).

Phenols. Acidity of phenols. Kolbe carboxylation of phenols. Benzyl carbon: outline of benzyl carbon reactions. Oxidation of the alkyl chains linked to benzene.

Aldehydes and ketones. Structure. Nomenclature. Preparation methods. Chemical and physical properties of the carbonyl group. Reactivity. Nucleophilic addition reactions: addition of alcohols, water, Grignard reagents, HCN. Addition of primary amines: formation of Schiff bases. Oxidation. Reduction of carbonyl compounds. Keto-Enol tautomerism.

Carboxylic acids. Structure and nomenclature. Physical properties. Preparation methods. Acidity. Effect of substituents on acidity in aliphatic acids; salts and soaps formation. Reactions of carboxylic acids. Reduction with LiAlH₄: formation of primary alcohols. Decarboxylation. Fischer esterification. Reaction with diazomethane: formation of methyl esters. Reaction with thionyl chloride: formation of acyl chlorides.

Functional derivatives of carboxylic acids. Acyl halides, esters, anhydrides, amides, nitriles: structure and nomenclature. Reactivity. Nucleophilic acyl substitution reaction. Addition of Grignard reagents to esters. Hydrolysis reactions of carboxylic acid derivatives. Reduction reactions.

Amines. Structure and nomenclature. Physical properties. Basicity. Preparation methods. Reactivity. Amine reactions with nitrous acid. Reactions of diazonium salts. Diazo-coupling. Azo dyes. Hofmann’s Elimination. Cope’s Elimination.
Course of Organic Chemistry and Lab I (Mod. 2)
Introduction to the organic chemistry laboratory: Safety regulations; Laboratory equipment: risks and use; Use of laboratory solvents.

Laboratory separation techniques: Purification of solids and purity criteria; Filtration, Crystallization, Drying, Sublimation. Distillation techniques. Extraction techniques of organic compounds. Boiling and melting point determination.

Chromatographic separations: The choice of the eluent, thin layer chromatography, column chromatography,

Laboratory experiences:
- Purification of an organic compound through recrystallization;
- Distillation and boiling point determination;
- Separation of organic products through solvent extraction;
- Caffeine extraction from tea leaves;
- Soap preparation;
- Pigment extractions from spinach leaves, and chromatographic separation;
- Thin layer chromatography;
- Aspirin synthesis

Textbook Information

Organic Chemistry and Lab I (Mod 1)
1) W.H. Brown – B.L. Iverson – E.V. Anslyn – C.S. Foote - “Chimica Organica”, con modelli molecolari - V Edizione EdiSES

2) B. Botta - “Chimica Organica” - Edi-ermes

3) D. Sica - “Esercizi di Chimica Organica” - EdiSES

4) W.H. Brown – B.L. Iverson – S.A. Iverson - “Guida alla soluzione dei problemi di Chimica Organica” - EdiSES

5) William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric Anslyn - Organic Chemistry - Cengage Learning (VI Edition)

6) Thomas N. Sorrell - Solutions to Exercises, Organic Chemistry - Univ Science Books

Power Point Slides can be downloaded by STUDIUM
Course of Organic Chemistry and Lab I (Mod. 2)
1. D. L. Pavia, G. M. Lampman, G. S. Kriz. Il laboratorio di Chimica Organica. Ed. Sorbona

2. M. D’Ischia. La Chimica Organica in Laboratorio. Ed. Piccin

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

4. K. L. Williamson, K. M. Masters. Macroscale and Miscoscale Organic Experiments. Ed. K. Williamson, Houghton Mifflin

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