66683 - Organic Chemistry I with Laboratory

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, polarimetry.

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

 

Readings/Bibliography

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).

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.

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 basic organic chemistry, see: http://www2.fci.unibo.it/~nanni/orgweb/

Teaching methods

Lessons supported by electronic 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.

Attendance to practical activities in the laboratory is compulsory and will be verified by signing the lists of attending students: only absences due to exceptional, acceptable reasons will be justified. 

As part of the teaching innovation project, supplementary digital teaching activities (DDI) will be organized to make up for any gaps in preparation.

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 course will give rise to a single mark (30 out of 30) resulting from the sum of the marks obtained in module 1 (theory, max 23 points) and module 2 (laboratory, max 10 points). Any score higher than 30 will result in 30 cum laude.

To pass the exam, however, a score of 12 or higher is required for module 1.

It is possible to take the module 1 exam only if the obligations of module 2 have been fulfilled (laboratory attendance, delivery of quizzes and reports).

MODULE 1 (THEORY)

The assessment of the knowledge acquired for module 1 takes place through the final exam only, which consists in a written test possibly followed by an oral test (generally on a different day from the written test and indicated on the Almaesami page as a note relating to the written test considered).

During the written exam, lasting 2 hours, the use of textbooks or notes will not be allowed, but periodic table, priority tables of functional groups, tables showing the pKa values may be used.

The written test will focus on the resolution of some organic chemistry exercises related to the application of the concepts learned during the theoretical course. In the text of the written test, the relative scores will be reported next to each exercise: the maximum total score achievable with this test will be 23.

The oral exam, which can be accessed with a minimum score of 12, is optional.

MODULE 2 (laboratory)

The evaluation of module 2 (max 10 points) will be performed through:

-evaluation of the answers to some quizzes distributed through the virtuale platform (max 1 point)
-correction of laboratory reports (max 1 point)
-final written test (max 8 points)

In detail, at the end of the first block of laboratory experiences (separation and purification techniques), quizzes regarding the experiences just completed will be distributed via the virtuale platform. The quizzes will have to be completed over a few weeks, and will give rise to the first score (max 1 point).

At the end of the second block of experiences (reactions), students will be asked to submit a report for each experience, which summarizes and comments on the results obtained. The reports will be corrected and returned within a few weeks, and will give rise to the second score (max 1 point).

Finally, a final written test will be prepared during the last week of the course. This final test consists of various exercises concerning the topics covered in module 2 of the course, and will last one hour. During the test, it will be possible to consult and use correlation tables of spectroscopic data, calculator, and periodic table, but not notes or textbooks. The evaluation of this test gives rise to the third score (max 8 points).

In the event of failure to participate in this last test, or scores deemed unsatisfactory by the student, it will be possible to repeat the test during the first session of the June exam session.

The score obtained for module 2 remains valid also for the academic years following the one of attendance of the course, with no time limits.

Teaching tools

Electronic presentations by the teachers will be available on-line.

Exercises of the various topics covered by the course and the relative solutions will be made available through the Virtuale platform as well as the texts of the exercises used for the previous exams and the relative solutions.

Office hours

See the website of Mariafrancesca Fochi

See the website of Luca Bernardi