CHEMISTRY - MODULE B
- Overview
- Assessment methods
- Learning objectives
- Contents
- Full programme
- Bibliography
- Teaching methods
- Contacts/Info
For Module B it is essential the knowledge of general chemistry concepts (eg electronic structure, theory of valence bond and molecular orbital, training and breaking of bonds, acis and bases, ...) that are considered preparatory to the understanding of organic chemistry.
The examination of Module B is a written text with exercises on nomenclature, chirality, reactivity, conformational stability, acidity and synthesis of organic molecules. Generally another question is on the description of the chemistry of a natural class of compounds (aminoacids and proteins, carbohydrates, lypids and nucleic acids).
Module B is designed to introduce and develop the fundamental concepts of organic chemistry for students who have previously assimilated the fundamentals of general and inorganic chemistry. The goal that arises is the knowledge i) of the Nomenclature of organic compounds and functional groups in organic chemistry; ii) the stereochemistry of organic molecules and their orientation in three-dimensional space; iii) the reactivity of the compound and how you can favor some transformations affecting kinetic and thermodynamic parameters; iv) the synthesis and the study which regards the possibility of preparing organic compounds of different molecular complexity. It will also be important to the acquisition of chemical concepts of natural compounds and the knowledge of the major classes of natural organic compounds such as carbohydrates, proteins, lipids and nucleic acids.
The main contents of the Module B can be summarized as follows:
1. Structure and bonding; acids and bases. What is organic chemistry. Nomenclature. organic functional groups and structures
2. Classes of organic compounds: alkanes, alkenes, alkynes, dienes, aromatic compounds, alkyl halides, organometallic compounds, alcohols, phenols, ethers, thiols, sulfides, aldehydes and ketones, amines, nitro compounds, heterocyclic derivatives, carboxylic acids and their derivatives .
3. The organic reactions. nucleophilic addition reactions, electrophilic addition, elimination, of nucleophilic substitution, electrophilic aromatic substitution, nucleophilic substitution reactions acyl
4. The substitution reactions in alpha to the carbonyl and the condensation reactions
5. Acidity and pKa.
6. Relocation and conjugation
7. The stereochemistry of the tetrahedral compounds
8. The chemistry of life and biomolecules: carbohydrates, amino acids, peptides, proteins, lipids and nucleic acids
The Periodic Table of the organic chemist. Historical definitions of organic chemistry. Properties of carbon. The structure of the atom. The orbitals. The chemical bond theory. Covalent chemical bonds and ionic bonds. Valence bond theory. Hybridization of orbitals: sp3 and methane structure. Structure of ethane. Sp2 orbitals and ethylene structure. Sp orbital and acetylene structure. Covalent bonds and electronegativity. Acids and bases: definitions of Bronsted-Lowry, definition of Lewis, values of pka. Organic compounds: alkanes. The functional groups. Alkanes and alkyl groups: the isomerism. The nomenclature of branched chain alkanes. The properties of alkanes: combustion and halogenation. The conformations of ethane. The representation of chemical structures. Cycloalkanes. Cis-trans isomerism in cycloalkanes. The conformations of cycloalkanes. Axial and equatorial bonds in cyclohexane. Conformational mobility of cyclohexane. Alkenes and organic reactions. The nomenclature of alkenes. The electronic structure of alkenes. Cis-trans isomerism in alkenes. Sequence rules: stereoisomers E, Z. The main types of organic reactions: addition, elimination, substitution, transposition. Reaction mechanisms: nucleophiles and electrophiles. Addition of HCl to ethylene. Reaction intermediates. Catalysis. The reactions of alkenes and alkynes. The addition of HX to alkenes. Markovnikov's rule. Structure and stability of carbocations. The addition of H2O to alkenes: hydration. The addition of X2 to alkynes: halogenation. Addition of H2 to alkenes: hydrogenation. Oxidation of alkenes: epoxidation. Epoxidation and hydroxylation. Dihydroxilation and oxidative cleavage of alkenes. Biological reactions of addition of alkenes. The addition of radicals to alkenes: polymers. Conjugated dienes. The stability of allylic carbocations: resonance. Resonance forms. Alkynes and their reactions. Addition reactions to alkynes. Acetylide anion formation. Aromatic compounds. The structure of benzene. Kekulè and the theory of resonance. The nomenclature of aromatic compounds. Electrophilic aromatic substitution reactions: halogenation, sulfonation, nitration, Friedel-Crafts alkylation and acylation reactions. Effect of the substituent in aromatic electrophilic substitutions. Interpretation of the effects of the substituents. Oxidation and reduction of aromatic compounds. Polysubstituted aromatic hydrocarbons. Organic synthesis. Stereochemistry and tetrahedral carbon. The chirality of molecules. Optical activity. The specific rotation. Pasteur's discovery and enantiomery. The sequence rules for assigning the configuration. The diastereoisomers. The meso compounds. The molecules with more than two stereocenters. Racemic mixtures and resolution of enantiomers. Physical properties of stereoisomers. Brief review on the isomerism. Chirality in nature. The alkyl halides. The nomenclature of halogenoalkanes. Haloalkanes preparation. The reactions of alkyl halides: the Grignard reagents. Nucleophilic substitution reactions. The SN2 reaction and the SN1 reaction. The elimination reactions: E2, E1 and E1cb. Summary of reactivity. Substitution reactions in living organisms. Alcohols, phenols, ethers and similar sulfur compounds. The nomenclature of alcohols, phenols and ethers. The properties of alcohols, phenols and ethers: the hydrogen bond. The properties of alcohols and phenols: acidity. Alcohol preparation methods. The additions of Grignard reagents. Reactions of alcohols. The synthesis and reactions of phenolsi Synthesis and reactions of ethers. Cyclic ethers: epoxides. Crown ethers. Thiols and sulphides. Aldehydes and ketones: the nucleophilic addition reactions. Carbonyl compounds. The nomenclature of aldehydes and ketones. Preparation of aldehydes and ketones. The oxidation of aldehydes. Nucleophilic addition to aldehydes and ketones. Nucleophilic addition of water: hydration. Nucleophilic addition of alcohols: the formation of acetals. Nucleophilic addition of ami
The Module A and Module B Course not provide for the adoption of a single reference text. Teachers recommend a set of books of general chemistry and organic chemistry (in Italian or English). Students can choose what suits them best. The set of suggested texts is not mentioned here because it can vary each academic year. In addition to the lessons, the teacher of Module B provides the projected slides, which are considered guidelines to the study, not substitute material of a textbook.
The student can choose one of these two texts for the Form B:
John McMurry - Fondamenti di Chimica Organica - 4a edizione Zanichelli
Janice Gorzynski Smith - Fondamenti di Chimica Organica - 3a edizione McGraw-Hill
Types of teaching activities
The educational activities of Modeule B consist only of lectures and at the end of the illustration of each new topic, exercises sessions are held on the subject in question.
Each of the two teaching modules provides a final test and given a rating. The outcome of each trial is thirty: the test is deemed passed if the candidate gets a vote of at least 18/30. The final grade is the average, weighted on the number of credits, the outcome of the two tests.
Evidence relating to the items of the Form A is a written exam of 3 hours. It is multiple choice questions in sufficient numbers to cover all the topics of the lectures, including the stoichiometry. Each correct answer is awarded 1 point, while the incorrect answers are assigned zero score.
Evidence relating to the Form B is a written exam lasting approximately 2.5 hours when there are questions in an open form, short-answer questions, and also multiple-choice questions on the entire program carried out during the course. Each correct answer is awarded a score, while wrong answers is attributed to non-scoring.
The total score obtained by the candidate in each written test is normalized so as to be out of thirty. Following the publication of the votes, the teachers of Form A and Form B provide the opportunity to view the writings by convening ad hoc candidates.
The lecturer is available to more details and clarifications on any requests made by the students receiving at his office by previous contact via email: andrea.penoni@uninsubria.it or by phone (031-2386440).