ORGANIC CHEMISTRY

Scienze Ambientali ORGANIC CHEMISTRY

0512700007
DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
EQF6
ENVIRONMENTAL SCIENCES
2022/2023

OBBLIGATORIO
YEAR OF COURSE 1
YEAR OF DIDACTIC SYSTEM 2022
SPRING SEMESTER
CFUHOURSACTIVITY
648LESSONS
224EXERCISES
112LAB
ExamDate
CHIMICA ORGANICA15/02/2023 - 15:00
Objectives
THE COURSE PROVIDES A SOLID BASIC CULTURE IN ORGANIC CHEMISTRY, SCIENCE BEHIND THE CHEMISTRY OF LIFE AND BIOLOGICAL PROCESSES.
THE COURSE PROVIDES KNOWLEDGE AND UNDERSTANDING OF THE BASIC PRINCIPLES OF ORGANIC CHEMISTRY. IN PARTICULAR IT ALLOWS THE LEARNING OF CHEMICAL LANGUAGE, THROUGH THE STUDY OF NOMENCLATURE, OF CHEMICAL-PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS IN THE DIFFERENT STATES OF AGGREGATION OF MATTER AND OF REACTIVITY OF ORGANIC MOLECULES, WHICH ARE INVOLVED IN BIOLOGICAL PROCESSES. THE COURSE PROVIDES ALSO THE LEARNING OF THEORETICAL BASES OF EXPERIMENTAL METHODS AND BASIC TECHNIQUES OF ISOLATION AND PURIFICATION OF ORGANIC COMPOUNDS.
LEARNING AND COMMUNICATION SKILLS ARE CONTINUOUSLY STIMULATED DURING THE COURSE, THANKS TO THE RESOLUTION OF ASSIGNED EXERCISES, WHICH ARE VERIFIED DURING THE LESSONS. EVEN THE AUTONOMY OF JUDGMENT AND THE CRITICAL SKILLS OF THE STUDENT ARE CONTINUOUSLY INCENTIVATED DURING THE LESSONS, THANKS TO THE WORK PERFORMED AT HOME AND THE EVALUATION IN THE CLASSROOM.
AT THE END OF THE COURSE THE STUDENTS WILL HAVE ACQUIRED SKILLS THAT ALLOW THEM TO KNOW HOW TO IDENTIFY, CLASSIFY THE ORGANIC COMPOUNDS AND UNDERSTAND THEIR PROPERTIES AND REACTIVITY.
THE STUDENT MAY APPLY THE KNOWLEDGE AND UNDERSTANDING CAPACITY ACQUIRED DURING THE COURSE ON SIMPLE ENVIRONMENTAL ISSUES CONCERNING, FOR EXAMPLE, THE MONITORING OF ORGANIC POLLUTANTS AND THE ANALYSIS OF ENVIRONMENTAL MATRICES.
Prerequisites
THE STUDENT MUST HAVE ACQUIRED THE KNOWLEDGE FROM THE COURSES OF GENERAL CHEMISTRY:
ELEMENTARY STRUCTURE OF THE ATOM AND INTRODUCTION TO THE CHEMICAL BOND - ATOMIC MODEL OF
SCHROEDINGER, QUANTUM NUMBERS, ORBITALS AND ELECTRONIC CONFIGURATIONS;
EQUILIBRIUM IN SOLUTION - IONIC PRODUCT OF WATER - PH - DEFINITIONS OF ACIDS AND BASES;
THERMOCHEMISTRY AND OUTLINE OF CHEMICAL THERMODYNAMICS - ENTHALPY AND BINDING ENERGY - ENTROPY
AND DISORDER - FREE ENERGY AND SPONTANEITY OF A CHEMICAL REACTION;
FREE ENERGY, EQUILIBRIUM CONSTANT AND DEPENDENCE OF THE EQUILIBRIUM CONSTANT FROM
TEMPERATURE;
CHEMICAL REACTIONS AND THEIR BALANCING.
Contents
- INTRODUCTION TO ORGANIC CHEMISTRY: THE ATOMIC STRUCTURE. BOND THEORY OF LEWIS. THE VSPER MODEL. THE THEORY OF MOLECULAR ORBITALS. THE RESONANCE. FUNCTIONAL GROUPS IN ORGANIC CHEMISTRY (3 HOURS)
- THE ALKANES: THE NOMENCLATURE OF ORGANIC COMPOUNDS. CYCLOALKANS AND CIS TRANS ISOMERS. CONFORMATIONAL ISOMERS, CONFORMATIONAL ANALYSIS OF THE ETHANE AND CYCLOALKANS. COMBUSTION. PETROLEUM AND GASOLINE. NUMBER OF OCTANS, ADDITIVES AND ENVIRONMENTAL PROBLEMS. (3 HOURS)
-ALKENES AND THEIR REACTIVITY: STRUCTURE, NOMENCLATURE AND PROPERTIES OF ALKENES. CIS/TRANS ISOMERS AND E / Z DESCRIPTORS. CLASSIFICATION AND MECHANISMS OF ORGANIC REACTIONS. ELECTROPHILIC ADDITION: HYDROALOGENATION, HYDRATION AND HALOGENATION. REDUCTION OF ALKENES. STEREOSELECTIVE REACTIONS. OXIDATION OF ALCHENES. (6 HOURS)
-STEREOCHEMISTRY: CHIRALITY. STEREOGENIC CENTERS, CHIRAL CARBONS. MOLECULES WITH A UNIQUE STEROGENIC CENTER, R / S CONFIGURATION. ORGANIC MOLECULES CONTAINING MORE THAN A STEREOGENIC CENTER. MESO COMPOUNDS. THE POLARIMETER: SPECIFIC ROTATION. REACTIONS WITH FORMATIONS OF CHIRAL COMPOUNDS. RACEMIC MIXTURES. (5 HOURS)
-ALKYL HALIDES: NOMENCLATURE AND PROPERTIES. THE NUCLEOPHILIC SUBSTITUTION. DEFINITION OF NUCLEOPHILICITY, COMPARISON WITH BASICITY. SN2, SN1 MECHANISMS: STEREOCHEMICAL FEATURES AND CONSEQUENCES. BETA ELIMINATION. ZAITSEF RULE. MECHANISMS E1 AND E2. STEREOCHEMICAL REQUIREMENTS. COMPARISON BETWEEN SUBSTITUTIONAND AND ELIMINATION IN PRIMARY, SECONDARY AND TERTIARY ALKYL HALIDES. (4 HOURS)
-ALCOHOLS, THIOLS AND ETHERS: NOMENCLATURE AND PROPERTIES, HYDROGEN BOND. ALCOHOLS AS ACIDS AND BASES. REACTIVITY OF ALCOHOLS: TRANSFORMATION IN ALKYL HALIDES , DEHYDRATION, OXIDATION. (4 HOURS)
-BENZENE AND AROMATIC COMPOUNDS: AROMATICITY: RULES OF HUCKEL. NOMENCLATURE OF BENZENE AND AROMATIC COMPOUNDS. TOXICITY OF AROMATIC POLYCYCLIC COMPOUNDS. REACTIVITY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION. ACTIVATING, DEACTIVATING AND ORIENTATION EFFECTS. OXIDATION OF THE BENZYLIC CARBON. (5 HOURS)
- PURIFICATION TECHNIQUES OF ORGANIC COMPOUNDS: CRYSTALLIZATION-CHOICE OF SOLVENT, EXPERIMENTAL PROCEDURES, MEASUREMENT OF THE MELTING POINT. LIQUID-LIQUID EXTRACTION, LIQUID SOLID EXTRACTION. CHROMATOGRAPHY. (3 HOURS)
-AMINES: STRUCTURE AND NOMENCLATURE OF AMINES. CHEMICAL-PHYSICAL PROPERTIES. BASICITY OF THE AMINES: COMPARISON IN BASICITY BETWEEN ALIPHATIC AND AROMATIC AMINES. (2 HOURS)
-ALDEHYDES AND KETONES: STRUCTURE, NOMENCLATURE AND PROPERTIES OF KETONS AND ALDEHYDES. REACTIVITY: NUCLEOPHYLIC ADDITION, FORMATION OF EMIACETALS AND ACETALS. OXIDATION OF ALDEHYDES AND REDUCTION WITH SODIUM BOROHYDRIDE. ENOLATES, ENOLS AND ALDOLIC CONDENSATION. (4 HOURS)
-CARBOXYLIC ACIDS AND DERIVATIVES: NOMENCLATURE AND STRUCTURE OF CARBOXYLIC ACIDS, CHLORIDES, ANHYDRIDES, ESTERS, AMIDS AND NITRILES. ACIDITY OF CARBOXYLIC ACIDS. ACYLIC NUCLEOPHILIC SUBSTITUTION: FISCHER ESTERIFICATION. HYDROLYSIS OF CARBOXYLIC ACIDS'S DERIVATIVES: SAPONIFICATION. REDUCTION OF CARBOXYLIC ACIDS AND DERIVATIVES WITH LITHIUM ALUMINUM HYDRIDE. (3 HOURS)
-CARBOHYDRATES: MONOSACCHARIDES, STRUCTURE AND STEREOCHEMISTRY D/L. MUTAROTATION. FORMATION OF ACETALS. REDUCING SUGARS. DISACCHARIDES AND POLYSACCHARIDES. (2 HOURS)
-AMINO ACIDS, PEPTIDES AND PROTEINS: STRUCTURE AND CHIRALITY OF ALPHA AMINO ACIDS. ACIDITY AND BASICITY OF ALPHA AMINO ACIDS. PEPTIDIC BOND. PRIMARY, SECONDARY AND TERTIARY STRUCTURE OF PROTEINS. (2 HOURS)
-LIPIDS: CLASSIFICATION OF LIPIDS. FATTY ACIDS, OILS AND FATS; SOAPS AND DETERGENTS, PHOSPHOGLICERIDES AND STEROIDS. (2 HOURS)

Teaching Methods
THE LESSON CONSISTS OF 48 HOURS OF LECTURES (6 CFU), WHICH ARE HELD IN THE CLASSROOM WITH THE AID OF PROJECTIONS. LECTURES ARE ON THEORETICAL ASPECTS OF ORGANIC CHEMISTRY.
AT THE BEGINNING OF THE COURSE A FOLDER WILL BE GIVEN TO STUDENTS, CONTAINING ALL THE DOCUMENTATION THAT IS PROJECTED DURING LESSONS.
IS STRONGLY SUGGESTED THE ATTENDANCE AT LESSONS.
Verification of learning
ACHIEVEMENT OF THE OBJECTIVES OF THE COURSE IS CERTIFIED BY PASSING WRITTEN AND AND ORAL EXAMINATION.
THE WRITTEN TEST (2 HOURS) IS PROPEDEUTICAL TO THE ORAL TEST. IT CONSISTS OF 6 EXERCISES: ONE DEDICATED TO THE NOMENCLATURE OF ORGANIC COMPOUNDS (10 POINTS), ONE TO THE MAIN STUDIED REACTIONS (8 POINTS), ONE TO A MECHANISM OF REACTION (4 POINTS), WHILE THE REMAINING THREE ARE DEDICATED TO THE MAIN CONCEPTS INTRODUCED (ISOMERS AND STEREOCHEMISTRY, ACIDITY AND BASICITY, AROMATICITY AND CHEMICAL-PHYSICAL PROPRTIES OF ORGANIC COMPOUNDS) (10 POINTS). THE ATTENDING STUDENTS WILL HAVE THE POSSIBILITY TO PASS TWO TESTS IN ITINERE, WHOSE POSITIVE RESULTS FREES THEM UP TO PASS THE FINAL WRITTEN TEST. THE MINIMUM MARK TO PASS THE TEST IS 16/32. THE MAXIMUM 32/32 WHICH CORRESPONDS TO 30 CUM LAUDE.
THE ORAL TEST, IN WHICH WILL BE ASKED SOME QUESTIONS ON THE TOPICS COVERED DURING THE COURSE, CONSISTS IN A DISCUSSION (MAXIMUM OF 40 MINUTES) AIMED TO ASSESSING:
- THE LEVEL OF KNOWLEDGE OF THE THEORETICAL CONTENT OF THE COURSE
- THE LEVEL OF COMPETENCE ACQUIRED IN SCIENTIFIC LANGUAGE, IN LOGIC CAPACITY AND ABILTITY TO SUMMARIZE ALL THE ANSWERS.
EVALUATION IS IN 30/30 AND RESULTS FROM AN AVERAGE OF THE WRITTEN AND ORAL SCORES.
THE MINIMUM SCORE 18/30 IS REPRESENTED BY THE ADEQUATE KNOWLEDGE OF BASIC REACTIONS GIVEN TO LESSONS, THE NOMENCLATURE OF ORGANIC COMPOUNDS AND THE STRUCTURE OF STUDIED BIOPOLYMERS.
THE MAXIMUM VOTE (30/30) IS AWARDED WHEN THE STUDENT SHOWS A COMPLETE AND IN-DEPTH KNOWLEDGE and is able to ESTABLISH CONNECTIONS BETWEEN THE TOPICS COVERED.
THE HONORS WILL BE AWARDED TO THE STUDENT WHO PRESENTS THE TOPICS COVERED FULLY, IN AN ERROR-FREE AND EXCELLENT WAY.
Texts
INTRODUZIONE ALLA CHIMICA ORGANICA, W.H. BROWN, SESTA EDIZIONE, EDISES S.R.L. –NAPOLI; FONDAMENTI DI CHIMICA ORGANICA, INTRODUZIONE ALLA CHIMICA ORGANICA, J. MC MURRY TERZA EDIZIONE, ZANICHELLI (BOLOGNA).
STUDENT SOLUTION MANUAL - INTRODUCTION TO ORGANIC CHEMISTRY (IV EDITION), F.S. LEE, W. BROWN, T. POON, JOHN WILEY & SONS, INC;
LECTURE NOTES.
-FOR THEORY ON THE PURIFICATION TECHNIQUES OF ORGANIC COMPOUNDS:
EXPERIMENTAL ORGANIC CHEMISTRY, R. M. ROBERTS; J. C. GILBERT; S. F. MARTIN
LECTURE NOTES
More Information
- COURSE LANGUAGE: ITALIAN
- FURTHER INFORMATION CAN BE FOUND ON GUIDEBOOK FOR STUDENTS AND REQUESTED BY E-MAIL: IIZZO@UNISA.IT
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