OVERVIEW

The course involves the continuation and in-depth study of the concepts covered by the Organic Chemistry I course. The topics covered allow you to acquire a more complete vision of the basic concepts of organic chemistry. Furthermore, they are largely chosen so as to be preparatory for subsequent courses such as Biochemistry and Pharmaceutical Chemistry.

AIMS AND CONTENT

LEARNING OUTCOMES

In-depth study of the reactivity of organic molecules through the study of difunctional compounds. Expansion of carbon-carbon bond formation reactions with particular attention to the construction of cyclic systems. Introduction to natural and heterocyclic organic substances.

AIMS AND LEARNING OUTCOMES

The aim of the Organic Chemistry II course is to provide more advanced concepts of the subject, compared to those learned in the previous Organic Chemistry I course. At the end of the lessons the student will have acquired theoretical knowledge on the structure and reactivity of bifunctional compounds, polycyclic aromatic compounds and heterocyclic compounds (aromatic and non-aromatic). He/she will also have explored the fundamental strategies for the formation of carbon-carbon bonds. This knowledge is fundamental for tackling future studies in the biochemical and pharmaceutical chemistry fields.
Specifically, the student will be able to:
• know the main classes of synthetic and natural organic compounds;
• apply the fundamental rules of the IUPAC nomenclature, in particular in the context of heterocycles;
• apply basic stereochemical knowledge also to more complex systems;
• think critically in order to apply the reactions studied to simple synthetic sequences for the production of required molecules, arguing the choices.

PREREQUISITES

Basic knowledge of the main topics of organic chemistry I.

TEACHING METHODS

The course includes three weekly lectures of two hours each, during which the students are taught all the notions relating to the organic chemistry teaching program.

Teaching materials to support the lessons (presentations, exercises, and in-depth articles) are provided to students through the aulaweb platform. Fundamental texts are recommended for the study of theory and for carrying out the exercises. However, part of the lesson is carried out on the blackboard, using digital media and molecular models to educate the student in the two- and three-dimensional design of molecules and in the carrying out of chemical reactions with the relative mechanism. To face dynamic frontal lessons, the active participation of students is required in answering questions and carrying out exercises individually or in groups. Quizzes and exercises will be available on the aulaweb platform to keep the study updated, which allows a profitable accompaniment of the lessons throughout the teaching period of organic chemistry.

Activities are planned to promote the ability to peer-review and self-evaluate the papers to promote the ability to learn to learn (basic level). The production of multimedia products is encouraged to develop functional alphabetic skills that allow the student to seek and process information, present, communicate and argue theories and practical concepts in both oral and written form (basic level).

Tips on how to study: 1) keep the study of the weekly topics updated, never let them accumulate; 2) study the material in small teaching units and make sure you understand each new section before moving on to the next; 3) solve all the problems of the chapter; 4) write during the study in a theory and exercise notebook; 5) learn by teaching and explaining (study better in a group); 6) use molecular models during the study.

Any Student with documented Specific Learning Disorders (SLD), or with any special needs, shall reach out to the Lecturer(s) and to the dedicated SLD Representative in the Department ( Prof. Luca Raiteri, Luca.Raiteri@unige.it ) before class begins, in order to liaise and arrange the specific learning methods and ensure proper achievement of the learning aims and outcomes. VERY IMPORTANT: any request for compensatory tools and adaptations in the exam MUST be done within 10 working days before the date of the exam according to the instructions that can be found at https://unige.it/disabilita-dsa/comunicazioni

SYLLABUS/CONTENT

1. ANALYSIS OF THE ORGANIC CHEMISTRY OF FUNCTIONAL AND BIFUNCTIONAL COMPOUNDS (28 hours)

• A1 Polycyclic and polyunsaturated systems and dicarboxylic acids

A1.1 Conformations of cycloalkanes and bicycloalkanes

• A1.1.1 Conformations in monocyclic alkanes
• A1.1.2 Conformations in fused bicyclic alkanes
• A1.1.3 Nomenclature and properties of bicyclic bridge systems

 A1.2 Dienes

• A1.2.1: UV-visible conjugation and absorption
• A1.2.2: Electrophilic additions to conjugated dienes
• A1.2.3: Pericyclic cycloadditions: the Diels-Alder reaction
• A1.2.4 Ring-closing metathesis reaction

A1.3 Dicarboxylic acids

A1.4 Polycyclic aromatic systems

• A1.4.1: nomenclature and properties
• A1.4.2: fullerenes, graphite, graphene, carbon nanotubes
• A1.4.3: arena oxides
• A1.4.4: electrophilic substitutions in naphthalene

A1.5 Biaryl systems

• A1.5.1 Chirality in biaryls
• A1.5.2 Suzuki reaction in the synthesis of biaryls and dienes

A2 Derivatives with two oxygen functions or with one oxygen function and one unsaturation

A2.1 Conjugated carbonyl and carboxyl compounds

A2.1.1 Preparation for: halogenation/elimination; crotonic condensation; Knoevenagel reaction; intramolecular metathesis; Wittig and Horner-Wadsworth-Emmons reactions

A2.1.2 Synthetic equivalence

A2.1.3 Nucleophilic conjugate addition reactions: reactions with mild nucleophiles, with organometallic derivatives, hydrides, Michael reaction

A2.1.4 Robinson ringing

A2.1.5 Conjugate additions in the biological world

A2.1.6 Conjugate additions and other reactions of enamines

A2.2 1,3-oxygenated compounds

• A2.2.1: Crossed aldol condensations with enolate preformation
• A2.2.2: Aldol condensations with synthetic equivalents of aldehydes
• A2.2.3 Oxidations with diacetoxyiodobenzene and Swern
• A2.2.4 Claisen and Dieckmann condensations
• A2.2.5 Biological aldol and Claisen reactions

 A2.3 1,2-oxygenated compounds (3 hours)

• A2.3.1 Retrosynthetic strategies: logical and illogical disconnects
• A2.3.2 Cyanide as an acyl anion equivalent.
• A2.3.3 Isonitriles: Passerini reaction
•  A2.3.4 Ditiani
• A2.3.5 1,2-Diols
• A2.3.6 Cyclic acetals

• A3 Radical reactions, phenols, quinones

 A3.1 Radical reactions

• A3.1.1: General principles
• A3.1.2: Radical polymerizations
• A3.1.3 Autooxidations
• A3.1.4 Antioxidants
• A3.2 Phenols as natural antioxidants
• A3.3 Quinones

2. HETEROCYCLIC COMPOUNDS (20 hours).

• B1 Classification and nomenclature of heterocyclic compounds

• B2 Electron-rich aromatic heterocycles

• B2.1 General characteristics
• B2.2 Synthesis and reactivity of pyrrole, furan, thiophene and related benzocondensed derivatives

• B3 Electron-poor aromatic heterocycles

• B3.1 General characteristics
• B3.2 Synthesis and reactivity of pyridine, quinoline and isoquinoline, pyrimidine, pyrazine, pyridazine

• B4 Aromatic pentaatomic heterocycles with two heteroatoms

• B4.1 General characteristics
• B4.2 Synthesis and reactivity of imidazole, oxazole, isoxazole

• B5 Tensioned saturated heterocycles: structure, synthesis and reactivity of oxiranes, aziridines, oxetanes and azetidines

RECOMMENDED READING/BIBLIOGRAPHY

• Chimica Organica di P. Y. Bruice, EdiSES
• Chimica Organica di W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote, EdiSES
• Chimica dei Composti Eterociclici di D. Sica, F. Zollo - EdiSES (l'ultima edizione)
• Chimica degli Eterocicli di G. Broggini, G. Zecchi – vol. 1 LaScientifica
• Chimica Organica di P. C. Vollhardt e N. E. Schore, Zanichelli
• Chimica Organica AA. VV. a cura di B. Botta Edi-Ermes
• Chimica Organica di M. Loudon, EdiSES
• Chimica Organica di J. McMurry, Piccin

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

The lessons start at the end of September following the official calendar

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

Written exam with open and/or multiple-choice questions. A self-correction phase will be introduced in your written exam by following the solution to the exercises carried out by the teacher on the blackboard. Subsequently, an evaluation of the papers will be carried out among the students (peer review). The self-evaluation process encourages reflection on one's work for responsible self-correction. Peer review stimulates discussion and in-depth analysis of the topics covered. After the correction, students will be informed of the score obtained and can ask for explanations. Those who obtain a pass will proceed to the oral exam.

During the course, an additional (optional) individual or group activity will be required to produce a video (maximum 10-12 minutes) on a topic covered in the classroom. Through the evaluation of the video, the transversal skills (communicative, functional, and social) of the student or the work group will be determined. The videos will be peer-evaluated through an evaluation rubric that will allow them to delve deeper into topics covered by other students.

ASSESSMENT METHODS

The written exam will include theoretical questions and organic chemistry exercises to be completed in three hours. The oral exam requires the student to be able to answer theoretical questions and solve exercises through which it will be possible to evaluate knowledge of the contents, quality, and organization of the presentation.The control tools provided in the teaching and examination methods, which accompany the teaching-learning process, aim to assess the students' levels of knowledge, skills, and competencies.