69074 - Organic Chemistry I

Course Unit Page

Academic Year 2018/2019

Learning outcomes

At the end of the class the student has a basic knowledge of the different types of organic compounds and the mechanism of the most important reactions. He will be able to solve problems concerning the transformation of simple organic molecules.

Course contents

Pre-requisites: the student should have a good knowledge of the laws and fundamental principles of general chemistry, such as the atomic structure, the nature of the chemical bond, the chemical equilibrium and the concepts of acidity and basicity.

Introduction. Chemical bond: ionic and covalent bonds. Atomic orbitals and molecular orbitals. Lewis structures. Resonance. Hydrogen interactions. Dipole-dipole interactions. Physical properties of organic molecules. Acids and bases. Functional groups in organic compounds and nomenclature rules.

Organic reactivity. Kinetics and thermodynamics of organic reactions. Arrhenious law. Activation energy. Intermediates and transition states in organic reactions. Homolytic and heterolytic cleavage of bonds. Nucleophiles and electrophiles. The idea of reaction mechanism. The language of organic chemistry.

Alkanes and cycloalkanes. Physical properties. Nomenclature. The sp3 carbon hybridization state. The structure of methane and ethane. The structure of cycloalkanes. Chair and boat conformations of cycloalkanes: axial and equatorial bonds. Substituted cycloalkanes. Cis/trans isomerism. The reactivity of alkanes: halogenation reaction.

Stereochemistry. Chirality and chiral molecules. Stereocenters. enantiomers and diastereomers. R/S configurations. More than one stereocenter. Meso forms.

Alkenes. Physical properties. Nomenclature. The sp2 carbon hybridization state. Cis-trans (E-Z) isomerism. Alkenes from alcohol dehydration. Addition to the CC double bond. Addition of halogen acids: the Markovnikov’s rule. Carbocations, carbon radical, carbanions: relative stability. Anti-Markovnikov products. Halogenation reactions.

Alkynes. The sp carbon hybridization state: acetylene. Nucleophilic reactions of acetylides.

Benzene. Structure and aromaticity.

Alcohols, ethers and phenols. Physical properties. Nomenclature. Acidity of alcohols and phenols. Organometallic reagents in alcohol synthesis. Grignard reagents.

Aldehydes and ketones. Physical properties. Nomenclature. The reactivity of the carbonyl group: the nucleophilic addition reaction. Acidity of "alpha" hydrogens. Keto-enol tautomerism. The aldol condensation. Emiacetal and, acetal formation. Oxidation reactions: Benedict and Tollens reagents.

Carboxylic acids and acyl derivatives. Physical properties. Nomenclature. The reactivity of the acyl compounds: the nucleophilic substitution at the carbonyl group. The esterification reaction. Base hydrolysis of esters [http://scholar.google.it/scholar?q=basic+hydrolysis+of+esters&hl=it&as_sdt=0&as_vis=1&oi=scholart&sa=X&ved=0ahUKEwjqju-jrsbPAhWDWxQKHTVUD9EQgQMIGjAA] .

Amines. Physical properties. Nomenclature. Basicity of aliphatic and aromatic amines. Synthesis of amine.

Carbohydrates. Monosaccharides (D‑glucose and D‑fructose). Fisher and Haworth structures. Anomers. Mutarotation. Disaccharides: sucrose, maltose, cellobiose. Polysaccharides: cellulose.

Readings/Bibliography

 

(1) W. H. BROWN "Chimica Organica" EdiSES, Napoli.
(2) W. H. Brown, C. S. Foote, B. L. Iverson, E. V. Anslyn "Chimica Organica" EdiSES, Napoli.

(3) W.H. Brown, T. Poon “Introduzione alla Chimica Organica” EdiSES, Napoli.

(4) B. L. Iverson, S. Iverson "Guida alla soluzione dei problemi" del testo citato al punto 2.

(5) T.W.G.SOLOMON "Chimica Organica" Ed. Zanichelli, Bologna.

(6) P.Y. Bruice “Chimica Organica” EdiSES, Napoli.

(7) R.J.FESSENDEN, J.S.FESSENDEN "Chimica Organica" Ed. Piccin, Padova.

(8) J.McMURRY "Chimica Organica" Ed. Piccin, Padova.

Teaching methods

Theoretical lectures. Problem solution.

Assessment methods

The goal of the final oral examination can be summarized as follows:
(i) the student must possess a good knowledge of the main concepts which are essential to understand structure and reactivity of organic molecules.
(ii) the student must be able to use the above concepts to solve simple problems of reactivity and structure in organic chemistry

Teaching tools

Discussion of problems in the classroom

Office hours

See the website of Andrea Bottoni