00148 - Organic Chemistry

Learning outcomes

The student will become familiar with carbon-based compounds, both of natural and synthetic origin. He/she will be able to attribute to organic compounds their systematic mane and classification based on

functional groups. The student will know the principles of stereochemistry and the most relevant reactions of organic compounds, with particular focus on their mechanism. The student will learn the

principles of the main spectroscopic and instrumental techniques used to characterize organic compounds, he/she will know how to interpret their results and how to combine information coming from

different techniques to identify and organic molecule.

Course contents

The course is split in two parts: (I) Organic Chemistry (9 UFC) and (II) Structural Characterization of Organic Compounds (3 UFC)

Part (I) provides knowledge on the fundamental principles of organic chemistry. At the end the student will know carbon-based compounds both of natural and synthetic origin, he/she will be able to attribute their systematic name and to cclassify compounds on the basis of theri functional groups. The candidate will know the principles of streochemistry and the main reactions of organic compounds with particualr reference to their mechanism. Part (II) will introduce the main spectroscopic techniques and their use in the structural characterization of organic molecules, also with the aid of classroom training sessions. At the end the candidate will know the priciples of instrumental techniques and will be able to interpret and discuss spectra in an integrated fashion to achieve the identification of an organic compound.

Organic Chemistry Programme (I)

(1) Covalent bonds and molecular shapes. The Lewis model, functional groups, bond angles and molecular shapes, resonance, the Valence Bond theory.
(2) Alkanes and cycloalkanes. Structure, constitutional isomery, nomenclature, conformation, cis-trans isomery in cycloalkanes, physical properties, reactions.
(3) Alkenes and alkynes. Structure, nomenclature, physical properties. Reactions and reaction mechanisms:  addition, oxidation, reduction, polymerisation.
(4) Stereochemistry. Isomery, chirality, enantiomers designation, Fisher projections, molecules bearing two or more stereocenters. Properties and separation of stereoisomers. Reactions yielding stereoisomers: stereospecific and stereoselective reactions. Meaning of chirality in biological systems and drugs.
(5) Acids and Bases. Acids and basis according to Brønsted-Lowry, quantitative measure of acids and bases strength, Lewis acids and bases.
(6) Alcohols, ethers, thiols. Structure, nomenclature, physical properties, reactions.
(7) Alkyl halogenides. Nomenclature. Aliphatic nucleophylic substitution. Mechanisms: NS1 and NS2, factors affecting the rates of NS1 and NS2 reactions. Beta-elimination: mechanisms E1 and E2. Williamson synthesis of ethers.
(8) Benzene and its derivatives. The structure of benzene. The concept of aromaticity. Aromatic etherocyclic compounds. Nomenclature. Phenols. Oxidation in benzylic position, electrophylic aromatic substitution.
(9) Amines. Structure and classification. Nomenclature. Physical properties. Reaction with acids. Reaction with nitrous acid: diazonium salts.
(10) Aldehydes and Ketones. Structure, nomenclature, physical properties. Reactions: addition of nucleophyles, formation of Schiff bases, tautomery, oxidation, reduction.
(11) Carboxylic acids. Structure, nomenclature, physical properties, acidity. Reactions: reduction, formation of esters conversion into acyl chlorides, decarboxylation.
(12) Derivatives of carboxylic acids. Structure and nomenclature. Reactions: with water, with alcohols, with amines, reduction. Interconversion of the functional groups.
(13) Enolate anions. Formation. Aldolic reaction. Claisen condensation..
(14) Natural compounds of relevant interest. Terpenes, polyphenols and quinones. Carbohydrates. Lipids. Aminoacids. and proteins. Nucleic acids.

Structural Characterization of Organic Compounds Programme (II)

(1) Fundamental principles of the spectroscopic techniques. The energy quantization principle. (2) Elements of Electronic spectroscopy. (3) Vibrational spectroscopy. (4) Nuclear Magnetic Resonance spectroscopy.  1H-NMR and 13C-NMR spectra. (5) Mass spectrometry. (6) Identification of an organic compound by the combined use of the different spectroscopic techniques. (7) Classroom training in the interpretation of spectra.

 

Readings/Bibliography

Organic Chemistry

W. H. Brown "Introduction to organic chemistry" 3rd edition, John Wiley & Sons, 2005.

 

Structural Characterization of Organic Compounds

G. F. Pedulli "Metodi Fisici in Chimica Organica" PICCIN, Padova, 1996.

 

 

Teaching methods

The course constitutes of classroom lectures dealing with the basics of organic chemistry and the principles and application of spectroscopic techniques. Lectures will be integrated by a few training sessions that will help the student get prepared for the written examination.

The teacher will continuously stimulate the students toward a critical attitude helping them to achieve a critical rationalization of the matter.
 
 

Assessment methods

The final examination consists of a written exam in two parts: Organic Chemistry and Structural Characterization of Organic Compounds. Such an exam will be followed by an oral examination (normally in the same day). To pass the written exam (mark 18/30 or higher) is a requisite to access the oral exam, which can be even delayed within the same “examination window”. The final mark will take into account the outcome of both exams without necessarily being the arithmetical average of the two.

 

Teaching tools

Lessons and training in classroom. A copy of the transparences/slides as well as the notes for Structural Characterization of Organic Compounds used during classes will be made available to all students.

Office hours

See the website of Luca Valgimigli

See the website of Riccardo Amorati