Università degli Studi di Urbino Carlo Bo / Portale Web di Ateneo


ORGANIC CHEMISTRY
CHIMICA ORGANICA

A.Y. Credits
2020/2021 12
Lecturer Email Office hours for students
Giovanni Zappia Wednesday 9.00 - 11.00

Assigned to the Degree Course

Pharmacy (LM-13)
Curriculum: PERCORSO COMUNE
Date Time Classroom / Location
Date Time Classroom / Location

Learning Objectives

The objectives of the course are to provide students with a good understanding of the theoretical and applicative aspects of organic chemistry. The primary objective of the course is to transmit students the language of organic chemistry, with particular reference to nomenclature, physical-chemical properties of the organic compounds and the structural characteristics of the functional groups. A particular focus will be on the structure, properties and reactivity of biomolecules, carbohydrates, amino acids, proteins and lipids.

Program

Introduction to Organic Chemistry. Chemical bonds and carbon hybridization states. Electronegativity. Acidity and basicity according to Brønsted-Lowry and Lewis.
Alkanes and cycloalkanes: structural and electronic aspects, nomenclature, constitutional isomerism. Cycloalkanes.
Alkenes: structure, nomenclature and isomeric E / Z. Main organic reactions, nucleophiles and electrophiles. Electrophilic addition reactions: hydro-halogenation mechanism. Intermediate reaction. Carbocations and their stability. Inductive effect. Hydration, halogenation. Rule of Markovnikov.
Alkyne: structure and nomenclature.
Benzene and aromatic compounds. Aromatic concept. Nomenclature of aromatic systems. Electrophilic Aromatic Substitution (SEAr): Benzene halogenation reaction: mechanism. Effect of substituents on reactivity and orientation. Activating and deactivating groups. Mesomeric effect and inductive effect. Disubstituted benzenes.
Alcohols and ethers. Structure and nomenclature. Phenols: acidity. Epoxides.
Stereoisomers. Chirality, enantiomers. Configuration notation R, S. Optical activity, polarimetry. Molecules with two or more stereocenters. Diastereoisomers. Physical and chemical properties of stereoisomers. Racemates. Meso compounds.
Aldehydes and ketones. Structure and nomenclature. Reaction of carbonyl carbon and acidity of hydrogen in alpha position. Nucleophilic addition reactions: mechanism of nucleophilic addition. Addition of alcohols: formation of emiacetals and acetals. Keto-enol tautomerism. Aldehyde condensation.
Carboxylic acids. Structure, nomenclature, acidity, chemical-physical properties. Carboxylic acid derivatives: acyl chlorides, anhydrides, esters, amides. Fischer Esterification. Alkaline esters hydrolysis.
Amines. Structure, classification and nomenclature. Basicity. Aliphatic amine basicity scale. Comparison with aromatic amines and amines.
Carbohydrates: aldose and ketose. Monosaccharides: glucose and fructose structure. Stereochemistry and relative configuration of sugars. D. series sugars. Fischer and Haworth projections. Open and cyclic structure. Glucose cyclic hemiacetal form. Anomeric effect.
Amino acids. Structure, acid-base properties and zwitterionic form. Relative configuration. Classification of protein amino acids. The peptide bond. Dipeptide.
Triglycerides: fats and oils. Soap and micellar aggregates. Saturated and unsaturated fatty acids. Catalytic hydrogenation of oils. Cis / trans isomerization.

Bridging Courses

General and Inorganic Chemistry

Learning Achievements (Dublin Descriptors)

Knowledge and understanding skills. The student will need to know the principles underlying the chemical bond, the nomenclature rules of organic compounds, be able to highlight the relationship between formulas, spatial structures and molecular properties.
The student will have to know the basic concepts of acidity and basicity according to Lewis rules, the stereochemistry, knowing and distinguishing enantiomers and the differences with the diastereo-isomers; the student will also have to master the Fisher Formulas.
The student must be able to identify the various functional groups, distinguishing between an aliphatic and an aromatic compound, the interactions between functional groups, their preparation and reactivity. The student will have to know the main biomolecules and relationships that bind the various functional groups that compose them and reactivity.
These skills will be verified through a written test and oral questions.
Ability to apply knowledge and understanding. The student should be able to use the various methods to describe an organic compound, nomenclature, symbols to express reaction mechanisms, resonance formulas and distinguish their energy weight. It will also apply the knowledge acquired to interpret basic acid / base properties of organic compounds.
The student will be able to synthesise and recognize organic compounds by applying the major stru-ctural and reactionary properties and the most important synthesis methods.
These skills will be evaluated through a written test.
Judgment autonomy. The student should be able to critically evaluate the structure and properties of an organic compound, both in terms of molecular complexity, stereochemistry, acid / base and reaction properties.
The knowledge acquired in the study of the different functional groups will find their full applica-tion in the student's ability to evaluate in their complexity biomolecular systems of interest for the purposes of the Study Course.
These skills will be verified both with the written test and with targeted oral application questions.
Communicative Skills. The student should be able to describe the structural and reactive concepts learned during the course by expressing it clearly, with appropriate terms and examples.
Learning ability. The student will have to be able to construct his or her scientific growth path in a critical and autonomous way, using the teaching material provided by the teacher in the form of texts and slides, as well as the in-depth material that he or she will be able to obtain. These skills, as far as possible, will be stimulated by the teacher by offering insights and providing exercises to be solved, which will then be explained and discussed during the lessons.

Teaching Material

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

Supporting Activities

AA.VV. "Chimica Organica " by B. Botta Edi Ermes 2012
P. Y. Bruice "Chimica Organica", III Edizione, Edises, 2017
Copy of slides of the lessons available in the Moodle platform › blended.uniurb.it


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