ORGANIC CHEMISTRY
- Overview
- Assessment methods
- Learning objectives
- Contents
- Full programme
- Bibliography
- Delivery method
- Teaching methods
- Contacts/Info
It requires a basic knowledge of stoichiometric ratios, of acid and base properties and electronegativity difference, the concepts provided in the course of General Chemistry
The organic chemistry test has made by both written and oral exam. The written part includes ten questions concerning all the arguments explained in the course. The students receiving at least 16/30 in the written test can deal with the oral part of the exam.
The test of the laboratory concerns only the oral description of the experiences made by the student.
The course of organic chemistry is immediately after the course of General and Inorganic Chemistry and it is its obvious continuation. In this way the student learns the concepts relating to the functional groups that are present in the molecules of a biological and which are subsequently discussed in the course of Biochemistry.
The Laboratory has the aim to acquaint at the student the various laboratory instruments making them autonomous on the laboratory work.
At the end of the course the student:
He will have recalled the notions relating to atoms, electronegativity and chemical bonds seen in previous courses
He will have understood the concepts of polar covalent bond, hybridization, sigma and pi bond, isomerism, resonance
He will be able to apply these concepts to the construction of organic molecules, to the identification of their arrangement in space, to the recognition of the functional groups present and to the assignment of the IUPAC name
The student will be able to critically analyze organic molecules based on their structure, recognizing their acidity / basicity, nucleophilicity / electrophilicity
The student will be able to evaluate the reactivity of organic molecules based on their structure and the environment in which they are found, identifying this reactivity
He will be able to build new substances by reaction of simple organic molecules
He will be able to perform simple laboratory operations to evaluate the degree of purity of inorganic salts and will be able to purify and isolate simple organic molecules
General aspects and nomenclature
Drawing of the structure of the organic molecules, hybridisation of C, N and O. Lengths and energy of bonds and effect of bond polarization on the reactivity of the functional group. Concept of Electrophile and of Nucleophile (2h).
Stereochemistry: definition of chirality. Enantiomers, racemic mixtures and diastereoisomers. Nomenclature R,S according to the CIP rule.
Functional group reactivities (2h).
ALKANES – conformation analysis of linear and cyclic molecules. Radical halogenations and order of radical stability (4h).
ALKENES – general mechanism of the reaction with Electrophiles and carbocation stability (Markovnikov rule). Mechanism of the addition of halogenidric acids, hydration (concept of catalyst). Reduction (catalytic hydrogenation) and oxidations (peracids and ozonolysis). Reactivity of conjugated dienes and concept of resonance (4h).
ALKYNES – addition of hydrogen halides and of water. Formation of enols. Reduction to alkenes or to alkanes (2h).
AROMATIC HYDROCARBONS – resonance and aromatic compounds. Reactivity of benzenes. The aromatic electrofile substitutions (nitration, halogenation, sulphonation and the Friedel -Craft reactions). Effect of the presence of a substituent on the aromatic ring. Nuclephilic aromatic substitution. Diazonium salts and Sandmayer reactions (4h).
ALKYL HALIDES - nucleophilic substitution reactions (Sn) and eliminations. Mechanisms and stereochemistry of Sn1, Sn2, E1 and E2 reactions. Synthesis and reactivity of organometallic compounds (Grignard) (4h).
ALCOHOLS – Reactions of oxidation and dehydration. Formation of leaving Groups (LG) from alcohols and protection of the hydroxyl (2h).
CARBONYLS – Reduction to alcohols with hydrides; nucleophilic additions (synthesis of acetals, cyanhydrins, imine and enamine); aldol condensation, reactivity of unsaturated carbonyls (Michael addition) (4h)
CARBOXYLIC ACIDS and DERIVATIVES – reaction mechanisms to synthetize Esters, Amide, Acyl halides and Anhydrides. Ester saponification and amide hydrolysis; Claisen condensation (2h).
AMINES – syntheses and reaction with carbonyls (mechanisms) (2h).
AMINOACIDS – structure and nomenclature of the natural AA. Definition of the isoelectric point. Peptide synthesis with mentions to protective and activating groups (2h).
CARBOHYDRATES – glucose and fructose. Anomeric carbon. Disaccharides (2h).
Contents of the Laboratory of Chemistry section
The students will deal with a series of different experiences related to the inorganic-analytical chemistry concerning acid –base titration (including the use of the pHmeter) (2h + 4h lab) and redox titrations (2h + 4h lab), Furthermore the students will face with experiences related to the organic chemistry, such as the extraction of caffeine from coffee (2h + 4h lab), the extraction and chromatographic separation of spinach pigments (2h + 4h lab).
General aspects and nomenclature
Drawing of the structure of the organic molecules, hybridisation of C, N and O. Lengths and energy of bonds and effect of bond polarization on the reactivity of the functional group. Concept of Electrophile and of Nucleophile (2h).
Stereochemistry: definition of chirality. Enantiomers, racemic mixtures and diastereoisomers. Nomenclature R,S according to the CIP rule.
Functional group reactivities (2h).
ALKANES – conformation analysis of linear and cyclic molecules. Radical halogenations and order of radical stability (4h).
ALKENES – general mechanism of the reaction with Electrophiles and carbocation stability (Markovnikov rule). Mechanism of the addition of halogenidric acids, hydration (concept of catalyst). Reduction (catalytic hydrogenation) and oxidations (peracids and ozonolysis). Reactivity of conjugated dienes and concept of resonance (4h).
ALKYNES – addition of hydrogen halides and of water. Formation of enols. Reduction to alkenes or to alkanes (2h).
AROMATIC HYDROCARBONS – resonance and aromatic compounds. Reactivity of benzenes. The aromatic electrofile substitutions (nitration, halogenation, sulphonation and the Friedel -Craft reactions). Effect of the presence of a substituent on the aromatic ring. Nuclephilic aromatic substitution. Diazonium salts and Sandmayer reactions (4h).
ALKYL HALIDES - nucleophilic substitution reactions (Sn) and eliminations. Mechanisms and stereochemistry of Sn1, Sn2, E1 and E2 reactions. Synthesis and reactivity of organometallic compounds (Grignard) (4h).
ALCOHOLS – Reactions of oxidation and dehydration. Formation of leaving Groups (LG) from alcohols and protection of the hydroxyl (2h).
CARBONYLS – Reduction to alcohols with hydrides; nucleophilic additions (synthesis of acetals, cyanhydrins, imine and enamine); aldol condensation, reactivity of unsaturated carbonyls (Michael addition) (4h)
CARBOXYLIC ACIDS and DERIVATIVES – reaction mechanisms to synthetize Esters, Amide, Acyl halides and Anhydrides. Ester saponification and amide hydrolysis; Claisen condensation (2h).
AMINES – syntheses and reaction with carbonyls (mechanisms) (2h).
AMINOACIDS – structure and nomenclature of the natural AA. Definition of the isoelectric point. Peptide synthesis with mentions to protective and activating groups (2h).
CARBOHYDRATES – glucose and fructose. Anomeric carbon. Disaccharides (2h).
Contents of the Laboratory of Chemistry section
The students will deal with a series of different experiences related to the inorganic-analytical chemistry concerning acid –base titration (including the use of the pHmeter) (2h + 4h lab) and redox titrations (2h + 4h lab), Furthermore the students will face with experiences related to the organic chemistry, such as the extraction of caffeine from coffee (2h + 4h lab), the extraction and chromatographic separation of spinach pigments (2h + 4h lab).
Textbooks:
Wade (traduzione Tagliatela Scafati), “Fondamenti di Chimica Organica” Prima edizione Ed. Piccin
B. Botta, “Chimica organica essenziale”, Edi-Ermes, milano 2012.
B. Botta, “Chimica Organica”, Edi Ermes, Milano 2011.
J. McMurry, “Fondamenti di Chimica Organica”, terza edizione, Zanichelli, Bologna 2005
Courseware
The slides presented in class, will be available on e-learning.
Frontal lessons
Upon appointment via email using, preferably, the official student’s address: @studenti.uninsubria.it