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, liquid-liquid extraction, crystallization and chromatography, the methodologies employed in simple organic reactions and the classic characterization methods (spectroscopy). 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).

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 assessment of learning is conducted through a series of tests distributed throughout the teaching semester and a final exam held during one of the sessions defined by the professors within the academic year during the exam periods arranged by the Degree Program.

Access to individual tests is allowed only through the AlmaEsami reservation system. Students not on the list will not be admitted to the tests. Any issues accessing the reservation system must be reported in a timely manner, and in any case, while the lists are still open.

The assessment of the laboratory module (maximum 33 points) will be carried out through:

- Evaluation of responses to some quizzes distributed via the virtual platform (maximum 4 points)
- Evaluation of the unknown test (maximum 7 points)
- Correction of laboratory reports (maximum 5 points)
- Final written test (maximum 18 points)

Specifically, during the first block of laboratory experiences (separation and purification techniques), quizzes related to the experiences will be distributed via the virtual platform, aimed at verifying the understanding of the experiences themselves. The quizzes must be completed by the end of the laboratory sessions and will result in the first score (maximum 4 points).

During the second block of experiences, students will perform a laboratory test consisting of the separation and identification of a mixture of unknown compounds. At the end of the test, students must fill out and submit a form that will result in the second score (maximum 7 points).

At the end of the second block of experiences (reactions), students will be invited to submit a report for one of the experiences performed, summarizing and commenting on the results obtained. The report will be corrected and returned within a few weeks and will result in the third score (maximum 5 points).

Finally, a final written test will be scheduled during the last week of the course. This final test consists of solving various exercises related to the topics covered in the laboratory module of the course and will last one hour. During the test, it will be possible to consult and use spectroscopic data correlation tables, calculators, and the periodic table, but not notes or textbooks. The evaluation of this test will result in the fourth score (maximum 18 points).

If a student fails to participate in this final test or obtains a score deemed unsatisfactory, it will be possible to retake the test a second time during the first session of the June exam period.

The laboratory module is considered passed with a score, given by the sum of the four evaluations, equal to or greater than 16/33.

The score obtained for the laboratory module remains valid even for academic years following the course attendance, without any expiration date.

The assessment of the theory module (maximum 33 points) will be carried out through the final exam alone, and it verifies the acquisition of the expected knowledge and skills through a written test.

During this test, lasting 2 hours, the use of textbooks or notes is not allowed, but the periodic table, tables of functional group priorities, and tables showing pKa values may be used.

The written test will focus on solving some organic chemistry exercises related to the application of concepts learned during the theoretical course. In the text of the written test, the relative scores will be indicated next to each exercise: the maximum total score achievable with this test will be 33 points. The written test is considered passed only if the score obtained is 18 or higher.

The overall grade for the Organic Chemistry I course with laboratory is obtained by summing the laboratory score (weighted at 30%) and the theory score (weighted at 70%), according to the following equation:

overall grade = lab score x 0.30 + theory score x 0.70

Scores above 30 will result in the awarding of honors.

Once the overall grade expressed in thirtieths is obtained, the student can either accept it as it is or try to improve it through an oral test that will take place on a day different from the written test, indicated on the AlmaEsami page as a note, but within the same session. It is not possible to take the written theory test and the oral test in different sessions.

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

See the website of Erica Locatelli