55393 - Organic Chemistry

Course Unit Page

SDGs

This teaching activity contributes to the achievement of the Sustainable Development Goals of the UN 2030 Agenda.

Good health and well-being Quality education Responsible consumption and production Climate Action

Academic Year 2021/2022

Learning outcomes

After learning, the student will have a basic knowlegde of structure, properties and reactivity of the main classes of organic compounds and of some natural organic products. The student will be able to: write and understand the structure of organic molecules; forecast the products and mechanism of simple organic reactions; handle organic substances in laboratory experiments.

Course contents

Electronic structure and hybridation of the carbon atom. Covalent bonds in organic molecules; electronic resonance.

Functional groups, nomenclature and representation of organic compounds. Structure and conformations of alkanes. Ring strain and conformations of cycloalkanes.

Stereochemistry of organic molecules: chirality, configuration and representation of chiral molecules; enantiomery and diastereoisomery, brief survey on optical acivity.

Elementary reaction mechanisms. Acids and based. Electropiles, nucleophiles and radicals. Representation of organic chemical reactions. Brief survey of thermodynamics, kinetics and reaction energy plots.

Main classes of organic compounds and their reactions:

Alkanes, origin, physical properties; combustion. Radicalic halogenations of alkanes;

Haloalkanes, nucleophilic substitution, SN1, SN2, stereochemistry of SN; elimination reaction E1 and E2. Brief survey on organometallic compounds;

Alkenes, Structure and isomers of C=C bond. Electrophilic and radicalic addition to C=C double bond, addition of alogenhydric acids, water, alcohols, hydrogen. Oxidations of alkenes: epoxidation, ozonolysis, dihydrixylation. Radicalic polymerization, principal alkenylic polymers;

Alkynes, structure of the triple bond; electrophilic addition to alkynes, hydrogenantion and semihydrogenetion of alkynes. Acidity of alkynes and reactions of alkynyl anaions;

Conjugated dienes, elementary knowledge of electronic structure of conjugated dienes, electronic transitions and photons assorbtion; 1,2 and 1,4 additions to dienes, allylic resonance;

Alcohols, ethers and epoxides, hydrogen bonding, acidity of alcohols; alkylation of alkoxides; oxidation of alcohols; nucleophilic substitution on alcohols and ethers; nucleophilic addition to epoxides;

Carbonyl componuds, nucleophilic addition to carbonyls, addition of organimetallic compounds, hydrides, water, alcohols, amines; hydrogenation of carbonyls; oxidation of aldehydes. Enolization, keto-enol tautomery, aldol reaction;

Acylic compounds, carboxylic acids, acyl halides, anhydrides, esters, amides; acidity of carboxylic acids. Nucleophilic acylic substitution, reactivity scale of acylic compounds and their interconversion reactions; possibly, basics on nitrils;

Amines, basicity of amines; alkylation of amines, reductive amination of carbonyl compounds;

Aromatic compounds, concept of aromaticity; aromatic electrophilic substitution, halogenations, nitration, sulfonation, Friedel-Crafts reactions; possibly, introduction to substituent effects. Phenols and anilines; brief survey on heterocyclic compounds and aromatic polycyclic hydrocarbons;

Natural products, carbohydrates, structure, stereochemistry, nomenclature of monosaccarids; di- and polysaccarides: lipids, fatty acids and triglicerids, surfactants and detergents; aminoacids, structure and stereochemistry, proteinogenic aminoacids; peptidic bond, polypeptides and proteins.

Exercises about all topics above mentioned.

Introduction to practical laboratory training: hazard connected to chemical substances and safety rules; main laboratory thecniques. Laboratory experimental training on: liquid-liquid extraction for the separation of organic mixures exploiting acid-base extraction; cross-aldol reaction between benzaldehyde and acetone; nucleophilic acylic substitution applied to paracetamol synthesis.

Readings/Bibliography

All the university Organic Chemistry texbooks are, generally, suitable.

Some possible suggestions:

P. Vollahrdt “Chimica Organica”, Zanichelli, Bologna

P. J. Bruice “Chimica Organica”, EDISES, Napoli

W. H . Brown, C. S. Foote, et al. “Chimica Organica”, EDISES, Napoli

J. McMurry “Fondamenti di Chimica Organica”, Zanichelli, Bologna

P. J. Bruice “Chimica Organica”, EDISES, Napoli,

Teaching methods

Lessons and discussion.

Classroom exercises.

Practical laboratory training.

As concerns the teaching methods of this course unit, all students must attend Module 1, 2 [https://www.unibo.it/en/services-and-opportunities/health-and-assistance/health-and-safety/online-course-on-health-and-safety-in-study-and-internship-areas] online, while Module 3 on health and safety is to be attended in class. Information about Module 3 attendance schedule is available on the website of your degree programme

Assessment methods

Written and oral exam and assessment of the laboratory reports

Teaching tools

PowerPoint videoprojection

Molecular models

Organic chemistry laboratory and instruments for practical training

Office hours

See the website of Paola Galletti

See the website of Chiara Samorì