ORGANIC CHEMISTRY I

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

Single discipline educational activity

Course Sheet

Course code:

00217

Academic Year of enrolment:

2021

Year of supply:

2022/2023

Type of Course:

Basic

Degree:

Course of Single Cycle Degree 5 years in MEDICINAL CHEMISTRY AND PHARMACEUTICAL TECHNOLOGY

Disciplinary Sector:

Organic Chemistry

Language:

Italian

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

FONTANA Antonella

Cycle:

First semester

Obligatory attendance:

Yes

Minimum hours of attendance:

Hours of classroom activity:

Individual study hours:

149

Prerequisites:

It is essential to pass the esam of General and Inorganic Chemistry
In fact it is essential that the student has the basic knowledge of General Chemistry to be able to take a course in Organic Chemistry

Objectives

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. The thermodynamic and kinetic foundations that govern the chemical behavior of organic molecules are essential tools that the course offers to students. The frontier topics with biochemistry and pharmaceutical chemistry are highlighted and treated with particular attention

Contents

* Introduction
* Alkanes and cycloalkanes
* Stereoisomers: Chirality and optical activity
* Alkenes and alkynes
* Aromatic compounds
* Alkyl halides: nucleophilic substitution and elimination reactions
* Alcohols, phenols and thiols
* Ethers
* Aldehydes and ketones
* Carboxylic acids and their derivatives
* Amines
* Carbohydrates
* Amino acids, peptides and proteins
* Nucleotides and Nucleic Acids

Extended Syllabus

* Introduction: Origins and history of organic chemistry - Organic compounds and life - The chemistry of carbon - Natural and synthetic organic compounds - Chemical bonding and isomerism: Chemical analysis and 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 - Petrochemicals - Physical Properties - Reactions of alkanes - Mechanism of photohalogenation * Stereoisomers: Chirality and optical activity - Enantiomers and racemates - Polarimetry - Properties of enantiomers - Absolute and relative configuration - Compounds with more than one chiral center - Diastereomers - Meso forms - Resolution of racemic mixtures * Alkenes and alkynes : Characteristics of multiple bonds - 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 polymerization: vinyl polymers - Cationic Polymerization - Acidity of alkynes * Aromatic compounds: Structure and Kekule resonance - Aromaticity - Calculation of the resonance energy - Nomenclature - Electrofilic aromatic substitutions: nitration, sulfonation , halogenation, Friedel-Crafts alkylation and acylation - Effect of the substituent in disubstitution reactions: activating or deactivating and ortho-para-or meta-orienting effects - ortho-Effect - Heterocyclic aromatic compounds * Alkyl halides: nucleophilic substitution and elimination reactions: Preparation of alkyl halides - Mechanisms of nucleophilic substitution: SN1 and SN2 - Mechanisms of elimination: E1 and E2 - Competition between substitution and elimination - Outline of Grignard reagents * Alcohols, phenols and thiols: Nomenclature and physical properties - Hydrogen bond - Acidity and basicity - Dehydration of alcohols - Reactions of alcohols with hydrogen halides - Oxidation of alcohols - Comparison between alcohols and phenols * Ethers: Physical properties and structure - Preparation - Ethers as solvents * Aldehydes and ketones: Nomenclature - Features of the carbonyl group - Nucleophilic Addition Reactions: addition of alcohols, water, hydrogen cyanide, ammonia and its derivatives, Grignard reagents - Oxidation-reduction reactions - Acidity of the alpha hydrogens - Keto-enol tautomerism - Exchange of deuterium - 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 and ammonolysis - Acyl halides, amides and anhydrides - Reactivity of acyl compounds * Amines: Classification, structure, nomenclature and physical properties of amines - Basicity and formation of ammonium salts - Preparations from alkylation of ammonia and reduction of other nitrogen compounds - Gabriel reaction - Ammines as nucleophiles - Diazonium salts and Sandmeyer reactions * Carbohydrates: Definition and 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, cellobiose, lactose and sucrose - Polysaccharides: starch, cellulose and glycogen - Sugar phosphates - Deoxy sugars - Ascorbic Acid * Amino acids, peptides and proteins: The natural amino acids - Acid-base properties - Determination of the isoelectric point - Chirality - Reactions of amino acids - The disulfide bond - Primary structure of proteins - Determination of the sequence structure - Secondary structure of proteins - Geometry of the peptide bond, hydrogen bond, helical and folded structure - Tertiary structure of proteins: fibrous and globular proteins - Quaternary structure of proteins * Nucleotides and Nucleic Acids: General structure and components - 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

Methods of Provision

Conventional

Teaching Methods

The course consists of approximately 72 hours of lectures. 12 hours are dedicated to guided exercises in the classroom

Evaluation methods

Verification of learning:

The exam consists of a written test including 8 problems, of which two on the part concerning biomacromolecules. The resolution of these problems allows to verify if the student has understood the fundamental bases of the reactivity of the molecules and their characterization. The scores of the individual problems vary from 2 to 5 depending on the difficulty of the exercise. The maximum achievable score is 32, corresponding to praise.
Current students have the opportunity to divide the exam in two parts performing to partial exams during the semester. These two partial exams include 10 exercises with a score of 3 point each. If the exercise is particularly well done, an additional half point is provided. Overcoming the two partial exams allows the student to pass the exam with a grade equal to the average of the marks obtained in the two exemptions. The partial exam is passed if the score exceeds 16/30.

Contacts/More Information

Slides projected during the course are available in pdf format on the course website. The lecturer is also available in the office hours for further clarification on the topics covered in class. Exercise hours are provided during the course delivery.
In the presence of ad hoc funds, a tutoring activity is provided in the Department of Pharmacy, with exercises scheduled from week to week.

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

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