ORGANIC CHEMISTRY

General Module

Course Sheet

Course code:

TE209

Academic Year of enrolment:

2021

Year of supply:

2021/2022

Type of Course:

Basic

Degree:

Course of 1st Cycle Degree in SUSTAINABLE TECHNOLOGIES AND ENVIRONMENTAL TOXICOLOGY

Disciplinary Sector:

Organic Chemistry

Is part of:

ANALYTICAL AND ORGANIC CHEMISTRY

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

SIANI Gabriella

Cycle:

Second semester

Obligatory attendance:

Yes

Minimum hours of attendance:

Hours of classroom activity:

Individual study hours:

102

Prerequisites:

Students must have acquired the basic notions of General and Inorganic Chemistry

Objectives

The Organic Chemistry course aims to provide the student with a solid basic knowledge of the structure and reactivity of organic compounds. The ability to deal with problems connected with the design and synthesis of organic compounds is stimulated and developed in the student. Links with biochemistry and pharmaceutical chemistry are emphasized with particular attention

Contents

The main purpose of the course is to provide the student with a solid basic knowledge of the structure and reactivity of the classes of organic compounds: from hydrocarbons to nucleic acids. At the end of the course the student knows how to correctly name and represent the structure of organic compounds, recognizes the functional groups and is clear about the concepts of structural isomerism, regio- and stereoisomerism. the fundamental reactions of organic compounds and their mechanism. The frontier topics with biochemistry, pharmaceutical chemistry and environmental chemistry are highlighted and treated with particular attention

Extended Syllabus

• Introduction: Organic compounds and life - The chemistry of carbon –
• Chemical bonding and isomerism: Molecular formula - Ionic and covalent bond – Structural formulas – Resonance – Hybridization and Molecular Structure
• Alkanes and cycloalkanes - Conformational and geometric isomerism: Structure of alkanes - IUPAC rules of nomenclature - Alkyl groups - Sources of alkanes - Physical Properties - Reactions of alkanes – Radical halogenation
• Stereoisomers: Chirality and optical activity - Enantiomers and racemates - Properties of enantiomers – Absolute and relative configuration - Compounds with more than one chiral center - Diastereomers - Meso forms - Resolution of racemic mixtures
• Alkyl halides: Preparation of alkyl halides - Nucleophilic substitution and elimination reactions: mechanisms of nucleophilic substitution SN1 and SN2; mechanisms of elimination: E1 and E2
• Organometallic compounds: Generality - Grignard reagents: use in the organic synthesis - Cadmium organic reagents
• Alcohols and thiols: Nomenclature and physical properties - Acidity - Synthesis of alcohols and thiols - Dehydration of alcohols - Reactions of alcohols with hydrogen halides - Oxidation of alcohols
• Ethers and Epoxides: Physical properties and structure - Synthesis and reactivity
• Alkenes and alkynes:  bond - Nomenclature and physical properties - Addition of halogen, hydrogen, acids and water - Electrophilic addition to asymmetrical alkenes of asymmetric reagents: the Markovnikov rule – Radical addition - Radical and cationic polymerization – Oxidation reaction of alkenes Acidity of alkynes - Stereospecific reductions of alkynes
• Conjugated dienes: Structure, conformations and reactivity - 1,4 addition reaction of conjugated dienes) - The Diels-Alder reaction
• Aromatic compounds: Structure and Kekule’ resonance – Aromaticity - - Nomenclature – Electrofilic aromatic substitutions: nitration, sulfonation, halogenation, Friedel-Crafts’ alkylation and acylation - Effect of the substituent in disubstitution reactions (reactivity and orientation) - Nucleophilic aromatic substitution reactions - Aryne intermediates - Heterocyclic aromatic compounds
• Phenol and derivatives: Structure, acidity and reactivity
• Aldehydes and ketones: Nomenclature - Features of the carbonyl group - Nucleophilic Addition Reactions: addition of alcohols, water, hydrogen cyanide, ammonia and its derivatives, Grignard reagents – Wittig reaction -Oxidation-reduction reactions - Acidity of the alpha hydrogens - Keto-enol tautomerism – alpha halogenation - Aldol condensation
• Carboxylic acids and their derivatives: Nomenclature and physical properties - Acidity: correlation between structure and acidity - Methods of preparation - Mechanisms of Nucleophilic acyl substitution - Esters - Fischer Esterification - Claisen Condensation – Acetoacetic synthesis and malonic synthesis - Saponification - Acyl halides, amides and anhydrides – Reactivity of acyl compounds
• Amines: Structure, nomenclature and physical properties of amines - Basicity and formation of ammonium salts - Preparations from alkylation of ammonia and reduction of other nitrogen compounds – Hofmann rearrangement - Gabriel reaction – Ammines as nucleophiles - Diazonium salts and Sandmeyer reactions
• Carbohydrates: Classification - Monosaccharides and their chirality - Fischer Projections - Cyclic structures of monosaccharides - Anomers and mutarotation - Pyranose and furanose forms - Reactions of monosaccharides: oxidation, reduction, formation of ethers, esters and glycosides - Disaccharides: maltose, lactose and sucrose - Polysaccharides: starch, cellulose and glycogen - Deoxy sugars
• Amino acids, peptides and proteins: The natural amino acids - Acid-base properties - Isoelectric point - Chirality - Reactions of amino acids - The disulfide bond - Primary structure of proteins - Determination of the sequence structure - Secondary structure of proteins - Tertiary structure of proteins: fibrous and globular proteins - Quaternary structure of proteins
• Nucleotides and Nucleic Acids: Primary structure of DNA - Double Helix - Notes on the function of nucleic acids.

Recommended Bibliography

• T. W. G. Solomons, C. B. Fryhle, Chimica Organica, 3a edizione italiana, Zanichelli, Bologna
• K. P. C. Volhardt, N.E. Schore, Chimica Organica, 4a edizione it. Zanichelli
• J. McMurry, Chimica Organica, 9a edizione, Piccin
• Brown, Foote, Iverson, Anslyn, Chimica Organica, 5a edizione, EdiSES

Teaching Methods

The course consists of 48 hours of frontal teaching. Each theoretical topic will be enriched with exercises in the classroom dedicated to the carrying out of exercises that will follow the topics of the lessons. The exercises will in part be carried out on the blackboard by the teacher, in part they will require the active participation of the students

Evaluation methods

Verification of learning:

The exam consists of a written test lasting 120 minutes. The written test included 6 open-ended questions with theoretical questions and exercises covering the entire program. The value of the exercises varies between 5 and 8 depending on the difficulty. The maximum achievable score is 33. If the score is 32 or higher, honors will be awarded. The teacher or student may also request an oral test which constitutes an additional element of assessment. In this case, the final mark will be established taking into account both the score obtained in the written test and in the oral test. It is important to underline that the oral test should not be understood as aimed at raising the mark obtained in the writings but, if it fails, the mark may be lowered even to the extent of rejection.
During the examination it is not allowed to consult books, notes or electronic devices of any kind

Contacts/More Information

The teacher receives the students every day by appointment to be agreed by e-mail

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

Aree