67062 - Organic Chemistry with Laboratory

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 Affordable and clean energy

Academic Year 2021/2022

Learning outcomes

When the course ends, the students develop a basic knowledge of the Organic Chemistry. The basics are: naming and structure of organic compounds; graphical drawing of the chemical structure of organic compounds, structure and reactivity of the functional groups, isomeric structures concepts, regio- and stereoisomerism, structure and reactivity of reactive intermediates. A second set of required concepts includes simple organic reactions: electrophilic and nucleophilic substitution to aliphatic and aromatic systems; addition and elimination reactions; nucleophilic addition and nucleophilic substitution to carbonyls. The students learn also the main experimental techniques employed in organic chemistry: distillation, solvent extraction, crystallization and chromatograpy, the methodologies employed in simple organic reactions and the classic characterization methods. Finally, the students grow sensitivity to the risks involved in the laboratory techniques, how to use the individual safety devices and how to manage and dispose of glass devices and chemicals.

Course contents

Prerequisites

  • Atomic structure and chemical bond - Schroedinger atomic model, quantic numbers, orbitals and electronic configurations;

  • Equilibria in solution - pH - Definitions of acid and base;

  • Termochemistry and introduction to chemical thermodynamics - Enthalpy and bond energy - Entropy and disorder - Gibbs energy and spontaneous chemical reactions;

  • Free energy, Equilibrium constant and its dependence on temperature;

  • Chemical reactions and their balancement.

Contents

Reminder of general chemistry. The organic compounds. Electronic effects of functional groups. Reactive intermediates and their stabilization.
Isomerism: structural isomers, regioisomers, conformational isomers (ethane, substituted ethanes, and cyclohexanes), configurational isomers (enantiomers, diastereoisomers, R/S absolute configuration, cis/trans isomers in cycloalkanes). 
The mechanisms of organic reactions. Kinetics, transition states and intermediates. Activation energy and reaction energy.

ALKANES. Natural sources and reactions. Mechanism of halogenation.

ALKENES. cis/trans (E/Z) isomers. Dienes and polyenes (isolated, conjugated, and cumulated). Preparation methods and reactions (electrophilic addition, reduction, oxidation, radical addition). Reactions of conjugated dienes.

ALKYNES. Acidity. Preparation methods and reactions (formation of salts, hydrogenation, electrophilic addition).

ARENES (aromatic hydrocarbons). Aromaticity. Benzene. Polynuclear and heteronuclear aromatics. Ortho, meta, and para positions in benzene. Sources of aromatics. Reactivity (electrophilic aromatic substitution in benzene and monosubstituted benzenes, nucleophilic aromatic substitution, oxidation).

HALOGEN DERIVATIVES. Preparation methods of alkyl and aryl halides. Reactivity of alkyl halides (reactions with metals, SN1 and SN2 nucleophilic substitutions, E1 and E2 eliminations). Reactions of aryl halides.

ALCOHOLS AND PHENOLS. Preparation methods of alcohols, phenols, and diols. Reactivity.

ETHERS, EPOXIDES, THIOLS, AND SULFIDES. Preparation methods and reactivity.

AMINES. Preparation methods and reactivity. Diatotization of aromatic amines: reactivity of diazonium salts.

Structure and reactivity of the CARBONYL GROUP. Nucleophilic addition and acyl substitution reactions.

ALDEHYDES AND KETONES. Preparation methods and reactivity. 

CARBOXYLIC ACIDS AND DERIVATIVES (ACYL HALIDES, ANHYDRIDES, ESTERS, AMIDES, NITRILES). Acidity of carboxylic acids. Preparation methods and reactivity of carboxylic acids and their derivatives.

ENOLATES. Reactivity of enolates of aldehydes and ketones (keto-enolic tautomerism, aldolic condensation). Reactivity of ester enolates (Claisen condensation). Reactivity of beta-ketoester enolates (acetacetic synthesis). Reactivity of beta-diester enolates (malonic synthesis).

LABORATORY

Safety in a laboratory of organic chemistry: products, apparatuses, standard procedures, waste disposal, common hazards, safe working practice, and emergency procedures.

Laboratory equipments and procedures: glassware, filtration devices, heating mantles and plates, stirring methods, vacuum pumps, rotary evaporators, equipment assembly, the laboratory notebook.

Base procedures in a laboratory of organic chemistry: distillation, extraction, crystallisation, thin-layer- and column-chromatography.

Characterisation of organic molecules: infrared spectroscopy, mass spectrometry, NMR spectroscopy, polarimetry.

Examples of synthesis, separation, purification, and characterisation of organic compounds (examples of simple reactions) with measurement of physical constants.

The chemical literature: the structure of chemical information and literature, Chemical Abstracts and Beilstein, on-line databases and resources.

Readings/Bibliography

Condensed texts:

  • J. McMurry, Fondamenti di Chimica Organica, IV Ed. Italiana, Zanichelli, 2011;

  • W. Brown, T. Poon, Introduzione alla Chimica Organica, IV Ed., EdiSES, 2011.

  • P. Yurkanis Bruice, Elementi di Chimica Organica, II Ed., EdiSES, 2017.

Expanded texts:

  • P. Yurkanis Bruice, Chimica Organica, III Ed. Italiana, EdiSES, 2017;

  • W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote, Chimica Organica, VI Ed., EdiSES, 2019 (linked to: B. L. Iverson, S. Iverson, Guida alla Soluzione dei Problemi, IV Ed., EdiSES, 2016);

  • J. McMurry, Chimica Organica, IX Ed. Italiana, Piccin, 2017;

  • Chimica Organica (a cura di B. Botta), edi-ermes, 2011;

  • D. E. Levy, Arrow Pushing in Organic Chemistry, Wiley, 2008 (II Ed, 2017).

Exercises:

  • M. V. D'Auria, O. Taglialatela Scafati, A. Zampella, Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica, Loghia Editrice (NA), IV Ed., 2017.

  • for exercises on baisc organic chemistry, see: http://www2.fci.unibo.it/~nanni/orgweb/

Lab texts:

  • R. M. Roberts, J. C. Gilbert, S. F. Martin, Chimica Organica Sperimentale, Zanichelli, Bologna, 1998;

  • H. Hart, L. E. Craine, Laboratorio di Chimica Organica, Zanichelli, Bologna, 1998.

Teaching methods

Lessons supported by electornic presentations, exercises, and practical activity in the laboratory (introduction during the lectures) performed by the students under the supervision of the teacher. The teacher is willing to receive students outside the lesson time for additional explanations and/or discussion.

Lessons and lab practice could be modified, due to the pandemic emergency, by directives by Italian authorities.

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

The assessment is done by a final exam only, which tests acquisition of the expected learning outcomes through a written exam that may be followed by an oral one (usually, but not always, on a different day indicated as a note on the Almaesami web page).

As the experimental Lab course is an essential part of the whole exam, attendance of the practical activity in the laboratory is compulsory: only absences due to exceptional, acceptable reasons will be justified (e.g. medical certificate).

During the laboratory activities the students should keep a laboratory notebook containing the detailed description of each experiment and the theoretical rationalisation of every experimental observation. At the end of the course, the lab notebook should be delivered to the teacher within TEN DAYS. Delivery of the notebook is compulsory for confirming lab attendance and for admission to the exam. Students who will not deliver their lab notebooks within ten days from the end of the course will be expected to attend again the lab course in the subsequent academic year. Evaluation of the notebook will be part of the final mark.

The final written exam will contain exercises related to both theoric (maximum grade will be 33/30) and lab Courses (maximum grade will be 33/30).

Only students passing the written exam (both tests >= 18 and weighted average of the two written tests >= 18) will be admitted to the oral exam, dealing, on the student's decision, with a further test on the whole Course contents. The students are free to accept the mark coming from the written exam without any additional test. The final mark will be given as a weighted average between the written exam (first test 70%, second test 25%) and the evaluation of the Lab notebook (5%). The oral exam, if positive, can add 3-4 points (out of 30) to the total mark. The oral exam must not be posponed to another date.

Just in case only one test is passed, the teacher reserves the right to offer the student to keep this result valid waiting for the other test to be passed.

During the exam, using of books/notes is not permitted, but the students will be allowed to refer to the Periodic Table, correlation tables of spectroscopic data, and priority tables of functional groups.

Exam procedures could be modified, due to the pandemic emergency, by directives by Italian authorities.

Teaching tools

PowerPoint presentations (whole course) and written lectures (laboratory section only) by the teacher will be available on-line.

Office hours

See the website of Daniele Nanni