ORGANIC CHEMISTRY

Alphabetic division AC-DL-MQ-RZ

Course Sheet

Course code:

00216

Academic Year of enrolment:

2017

Year of supply:

2018/2019

Divisions:

Cognomi A-G

Type of Course:

Basic

Degree:

Course of Single Cycle Degree 5 years in PHARMACY

Disciplinary Sector:

Organic Chemistry

Is part of:

ORGANIC CHEMISTRY

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

ANGELINI Guido

Cycle:

First semester

Obligatory attendance:

Yes

Minimum hours of attendance:

Hours of classroom activity:

Individual study hours:

228

Prerequisites:

Necessary knowledge for the learning of Organic Chemistry:
Electronic configuration and atom structure ▪ ionic and covalent bonds ▪ molecular structures ▪ atomic orbitals and resonance structures ▪ hybrid orbitals of carbon, oxygen and nitrogen ▪ acidity and basicity according to Brønsted-Lowry and Lewis ▪ definition of pKa.
The General and Inorganic Chemistry is the mandatory exam before taking Organic Chemistry

Objectives

The course is based on the study of the nomenclature, the reactivity and the preparation of organic compounds, with reference to the physico-chemical and biological properties for the pharmaceutical applications. The ability to recognize the functional groups, the understanding of the reaction mechanisms and the critical analysis of the stereochemical aspects represents the aims of the course.

Learning results:

Knowledge and skills
- nomenclature and properties of the functional groups;
- reactivity of organic molecules like acids, bases, electrophiles and nucleophiles.
- assign the name to organic molecules second to the IUPAC rules;
- recognize the different types of chemical reactions and complete the reaction schemes.
Self-judgment
- ability to discuss the reactions mechanisms;
- ability to discuss the stereochemistry of the obtained molecules.
Communication abilities
- demonstrate scientific language and chemical symbolism;
- ability in designing organic compounds from the molecular structures to the three-dimensional representations.

Contents

Structures and Bonding: Acids and Bases; Nomenclature, Structures, Physical Properties, Stereochemistry and Reactivity of Alkanes and Cycloalkanes; Alkenes and Alkynes; Aromatic Compounds; Organohalides; Alcohols-Ethers-Thiols and Sulfurs; Aldehydes and Ketones; Carboxylic Acids and Derivatives; Amines; Carbohydrates; Amino Acids; Natural Compounds and Nucleic Acids.

Extended Syllabus

Introduction to the study of Organic Chemistry: atomic structure; electron configurations; chemical bonding nature; polar covalent bond; electronegativity and dipole moment. ● van der Waals and London forces ● hydrogen bonding ● formal charges and resonance; rules for resonance forms ● hybridization of carbon: sp3; sp2 and sp orbitals ● hybridization of oxygen and nitrogen ● acids and bases: the Brønsted-Lowry definition; acid and base strength; predicting acid-base reactions from pKa values; the Lewis definition; organic acids and organic bases ● electrophiles and nucleophiles in organic chemistry. Alkanes and Cycloalkanes: structures and properties ● common and IUPAC nomenclatures ● conformations of ethane ● conformation and stability of cycloalkanes ● cis and trans isomerism ● mechanism of the radical reaction: addition of halogens ● energy diagrams and transition states ● hybridation and stability of the radical intermediate ● hyperconiugation ● reactivity vs selectivity: Cl2 vs Br2. Alkenes: structures and properties ● cis and trans isomerism in alkenes ● nomenclature and sequence rules: the E, Z designation ● electrophilic addition of HX: the Markovnikov's rule; carbocation structure, stability and rearrangements ● addition of halogens: halohydrin formation ● addition of water ● oxymercuration and hydroboration ● addition of carbenes ● hydrogenation and oxidation reactions ● hydroxylation and cleavage ● addition of HBr in the presence of peroxides ● polymerization ● Diels-Alder cycloaddiction. Alkynes: structures and properties ● nomenclature ● preparation ● electrophilic addition of HX and halogens ● hydration ● reduction and oxidative cleavage ● alkyne acidity: formation of acetylide anions and alkylation of acetylide anions. Stereochemistry: chirality and optical activity ● tetrahedral carbon and enantiomers ● specific rotation ● physical properties of enantiomers ● sequence rules for specification of configuration ● diastereomers ● meso compounds ● racemic mixtures and their resolution ● Fischer projections ● chirality in Nature. Alkyl Halides: structures and properties ● nomenclature ● preparation ● Grignard reagents ● nucleophilic substitutions and eliminations ● stereochemistry and kinetics of the SN2 and SN1 ● stereochemistry and kinetics of the E2 and E1 ● the Zaitsev's rule. Alcohols: structures and properties ● nomenclature ● preparation ● acidity and basicity ● oxidation reaction. Ethers, Epoxides, Thiols and Sulfides: structures and properties ● nomenclature ● preparation ● acidity and basicity ● the Williamson synthesis ● ring-opening reactions of epoxides ● crown ethers and phase-transfer catalysts in organic reactions. Benzene and Aromaticity: structures and properties ● nomenclature ● molecular orbital description of benzene ● aromaticity ● the Hückel rule ● electrophilic aromatic substitution ● halogenation; the Friedel-Crafts alkylation; acylation; nitration and sulphonation of aromatic rings ● substituent effects ● nucleophilic aromatic substitutions ● pyridine and pyrroles ● acidity and basicity of phenols ● the Kolbe reaction and the synthesis of acetylsalicylic acid ● polycyclic aromatic compounds. Heterocycles Compounds: structures ● nomenclature ● five-membered unsaturated heterocycles: pyrrole, furan, and thiophene ● electrophilic substitution reactions ● six-membered heterocycle: pyridine ● basicity and electrophilic substitution of pyridine ● N-oxide pyridine formation ● nucleophilic substitution of pyridine. Aldehydes and Ketones: structures and properties ● nomenclature ● preparation ● nucleophilic addition reactions: relative reactivity of aldehydes and ketones; addition of H2O; HCN; Grignard reagents; hydride; amines and alcohols ● the Wolff-Kishner reaction ● the Clemmensen reaction ● the Wittig reaction ● the Cannizzaro reaction ● the keto-enolic tautomerism ● conjugate nucleophilic addition to alpha, beta-unsaturated aldehydes. Carboxylic Acids: structures and properties ● nomenclature ● preparation ● dissociation of carboxylic acids ● substituent effects on acidity ● carboxylic acid derivatives ● nucleophilic acyl substitution reactions ● chemistry of acid halides; acid anhydrides; esters; amides; nitriles ● the Claisen condensation reaction● the Stork reaction ● Fischer esterification reaction ● esters saponification: surfactants and supramolecular aggregation ● malonic esther synthesis ● acetoacetica esther synthesis. Amines: structures and properties ● nomenclature ● preparation ● acidity and basicity ● chirality of tertiary amines ● reactions of amines and arylamines ● diazonium salts and Sandmayer reaction ● tetraalkylammonium salts as phase-transfer catalysts in organic reactions ● the Gabriel synthesis ● the Hoffmann transposition ● the Hoffmann elimination. Carbohydrates: structures and properties ● nomenclature ● classification ● configurations of monosaccharides ● Fischer projections ● D and L series of the aldoses ● the Killiani-Fischer synthesis of monosaccharides ● cyclic structures of monosaccharides: hemiacetal formation and anomers ● mutarotation ● isomerisation reaction ● reduction and oxidation reactions of monosaccharides ● glycosides formation ● structures of disaccharides and polysaccharides in Nature. Amino Acids: structures and properties ● nomenclature ● classification ● acidity and basicity ● isoelectric point calculation ● the Strecker synthesis of alpha-amino acids ● resolution of R, S amino acids ● the sulphur bonding ● structure of peptides and proteins. Organic Compounds in Nature: biomolecules ● lipids and phospholipids ● fats and oils ● chemistry and properties of ascorbic acid. Nucleic Acids: structures and composition of DNA and RNA ● the Watson-Crick model.

Recommended Bibliography

Bruice, Organic Chemistry, Edises (3rd ed.); McMurry, Organic Chemistry, Piccin (7th ed.); Brown-Brent- Anslyn-Foote, Organic Chemistry ,Edises (5th ed.); Solomons-Fryhle, Organic Chemistry, Zanichelli (3rd ed.); Bruno Botta, Chimica Organica, Ediermes (II edizione).

Teaching Methods

Lessons and exercises in classroom for a total of 72 hours take place 7 hours a week. After explanations of a given argument by using slides (PowerPoint) or dashboard, professor solves exercises previously assigned in the exam sessions (available online on the web page of the department) by using Tablet PC in order to demonstrate the level of difficulty of the exam. Molecular models are also available and employed during the course to facilitate the comprehension of stereochemistry.

Evaluation methods

Verification of learning:

The exam is divided into two parts. Each part must be passed in the same session. The first part consists of a two-hour test in which students have to write the correct solutions to six problems:
1) drawing molecular structures from the IUPAC names and vice versa;
2) completing reaction mechanisms starting from the reagents with particular attention to the stereochemistry of the products;
3) completing a multi-step reaction writing the missing reagents or the missing products;
4) discussing about aminoacids or carbohydrate reaction and properties;
5) general knowledge and comprehension of functional groups and their reactivity and properties as nucleophiles and electrophiles;
6) discussing the strength of given compounds as acid or base by comparing pKa values; .
Only students graded with a positive score (from a minimum of 18/30 to a maximum of 30/30) can access the second part: an oral exam in which they have to show their level of mastery by using appropriate symbols and formulae to describe transition states, intermediates, tautomerism, and acid-base equilibria, starting from the analysis of their test.

Contacts/More Information

Professor encourages students to ask questions during the lessons or office hours. Tests of previous exam sessions are available online on the web page of the Department and on the professor’s page (https://sites.google.com/site/chimicaorganicangelini/). The Organic Chemistry books are freely available in the Library of the Department.

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

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