OVERVIEW

The importance of organic chemistry in the field of Materials Science has been growing steadily, with the design and fabrication of ever new organic materials having a wide variety of properties and functions. For Biological Sciences organic chemistry is essential in order to understand the mechanisms of livinf beings. For both a fundamentalknowledge of the principle of organic chemistry is therefore essential.

This module is organized in order to lead the students to understand the basic principles and thus to be able to understand and manipulate formulas and reaction equations without an excessive notionalism.

The laboratory work will introduce the most important separation methods and will train the students to work i  groups and to report their experimental findings in a correct way.

AIMS AND CONTENT

LEARNING OUTCOMES

Acquire basic knowledge regarding the nomenclature, structure and reactivity of the main organic compounds; acquire practical skills regarding simple experimental procedures.

AIMS AND LEARNING OUTCOMES

The objective of the teaching is to provide the basic knowledge of Organic Chemistry, useful for being able to relate structural properties and chemical behavior of the main classes of organic compounds. The teaching is completed with classroom exercises (mainly to learn rules of nomenclature and stereochemistry) and some laboratory experiences that introduce the student to the practical aspects of the subject.

At the end of the lectures, the student will thus have acquired: theoretical knowledge about the structure and reactivity of organic molecules and practical skills in applying separation techniques and performing simple chemical reactions.

PREREQUISITES

A good knowlege of general and inorganic chemistry

TEACHING METHODS

The module gives 8 credits (Biological Sciences) or 9 credits (Material Sciences).

There will be lessons in presence in a classroom and laboratory work.

Lessons are 54 hours (Bioogical Sciences) or 60 hours (Material Sciences). Attendance to lessons is not mandatory. However, those who attend at least 2/3 of the lessons will have a bonus for the written exam (see the appropriate section). Moreover, those, who pass at least 3 of 4 intermediate tests (that will be repeated twice each) will have a further bonus. Note: this latter bonus may be also gained by those who are not able to attend the lessons. Those who, for demonstrated reasons, can not attend, may be allowed by the teacher to access the lesson recordings.

Attendance to laboratory work (16 hours for Biological Sciences and 20 hours for Material Sciences) is mandatory. The students will be divided in three periods. All Material Science students will be in the first one. For biological Science, they will be divided into the three periods according to their preference and/or by their situation related to previous exams (especially General Chemistry). The periods will be:

• november- december
• january
• march

The students will write a report on the labioratory work, that will be read and corrected by the teacher. Laboratory work will be carried in pairs, and also the reports will be written in pairs.

Students are expected to spend (Biological Sciences or Material Science): 54-60 hours for attending lessons. 16-20 hours for laboratory work. 8-10 hours for writing the lab reports. 10 hours for sitting the intermediate tests. 5 hours for trying on aulaweb the written exam. Finally: 107-120 for individual study.

SYLLABUS/CONTENT

LESSONS (54 hours for both degree courses)

1) Fundamental concepts (11 hours)

• 1.1 Introduction
• 1.2 Chemical bond in organic compounds
  • 1.2.1: electronic configuration, valence shell.
  • 1.2.2: Lewis and Kekulé formuals. Noble gas rule.
  • 1.2.3: Electronegativity, covalent and ionic bonds
  • 1.2.4: Formal charge determination
  • 1.2.5: Resonance. Use of curved arrows
  • 1.2.6: Molecule shape. Bond angle. VSEPR theory.
  • 1.2.7: Molecular orbital theory. Hybrid orbirtals. Sigma and Pi bonds
• 1.3 Alkanes
  • 1.3.1: Molecular formula and constitutonal formula. Isomerism. Chemodiversity of alkanes
  • 1.3.2: Classification of carbon atoms
  • 1.3.3: Alkane nomenclatureNomenclatura degli alcani. Naming of monovalent and bivalent radicals
  • 1.3.4: Natural sources of alkanes
  • 1.3.5: Octane number
  • 1.3.6: The concept of functional group
• 1.4 Overview of the main classes of organic substances with elements of nomenclature
  • 1.4.1: alkenes, alkynes, arenes, alcohols, phenols, aldehydes, ketones, carboxylic acids, amines, ethers, esters, amides.
  • 1.4.2: Priority of functional groups in nomenclature
• 1.5 Intermolecular interactions and physical properties
• 1.6 Acid-base properties of organic compounds
  • 1.6.1: Recap of fundamental concepts of acid-base equilibria (Bronstend-Lowry)
  • 1.6.2: Factors that may influence acidity
  • 1.6.3: Acid properties of alcohols, thiols, alkynes, phenols, carboxylic acids, amides.
  • 1.6.3 Basic properties of alcohols, aliphatic and aromatic amines, amides, guanidine

2) Stereochemistry and conformations (6 hours)

• 2.1 Diversity of 2 substances
• 2.2 Conformations
  • 2.1.1: ethane
  • 2.1.2: butane
  • 2.1.3: cycloalkanes
  • 2.1.4: cyclohexane
• 2.3 Stereoisomer types
• 2.4 Deawing using dashed and wedged lines
• 2.5 Chirality. Stereogenic centres
• 2.6 R/S notations
• 2.7 Compounds with 2 stereogenic centres
• 2.8 Optical activity
• 2.9 Mixtures of enantiomers
• 2.10 Fischer formulas
• 2.11 Equivalent stereogenic centres
• 2.12 Chemical properties of enantiomers
• 2.13 Chirality in the living world
• 2.14 E/Z isomery in alkenes

3) General concepts on organic reactions and additioon reactions to alkenes (4 hours)

• 3.1 General concepts on thermodynamics and kinetics of organic reactions. Catalysis
• 3.2 Classification of reactions
• 3.3 Reaction mechanisms: electrophiles and nucleophiles
• 3.4 Hydrogenation of alkenes
• 3.5 Electrophilic additions to alkenes. Markovnikov rukle
• 3.5.1 Addition of hydrogen halides
• 3.5.2 Addition of water
• 3.5.3 Addition of halogens

4) Aromatic compounds (4 hours)

• 4.1 Benzene and aromaticity
• 4.2 Nomenclature of benzene derivatives
• 4.3 Aromatic electrophilic substitutions
  • 4.3.1 General concepts
  • 4.3.2 Halogenation
  • 4.3.3 Nitration
  • 4.3.4 Friedel-Crafts alkylation with alkenes
  • 4.3.5 Friedel-Crafts acylation
  • 4.3.6 Sulphonation. Use of sulphonates as surfactants
  • 4.3.7 Activating/deactivating and orienting effects of substituents
• 4.4 Heteroaromatic compounds
  • 4.4.1 Structure and names
  • 4.4.2 Basic properties

5) Laboratory  (6 hours)

• 5.1 Crystallization
• 5.2 Distillation
• 5.3 Liquid-liquid extraction
• 5.4 Chromatography

6) Reactivity of C=O bonds (8 hours)

• 6.1 Nucleophilic additions to carbonyl groups
  • 6.1.1 General concepts
  • 6.1.2 Addition of water
  • 6.1.3 Addition of alcohols, also followed by substitutions.
  • 6.1.4 Addition of primary amines
• 6.2 Keto-enol tautomery
• 6.3 Acyl nucleophilic substitutions
  • 6.3.1 General concepts: thermodynamic and kinetic aspects. Different reactivity of carboxylic derivatives
  • 6.3.2 Synthesis and hydrolysis of acyl chlorides
  • 6.3.3 Synthesis and hydrolysis of anhydrides
  • 6.3.4 Synthesis and hydrolysis of esters
  • 6.3.5 Synthesis and hydrolysis of amides
• 6.4 Other carboxylic-type derivatives
  • 6.4.1 Nitriles
  • 6.4.2 Derivatives of carbonic acid
  • 6.4.3 Derivatives of sulphonic acids
  • 6.4.4 Derivatives of inorganic oxyacids
• 6.5Reactivity at the alpha position of carbonyl/carboxylic compounds
  • 6.5.1 Acidity of the alpha position
  • 6.5.2 Aldol reaction and crotonic condensation

7) Redox reactions of organic compounds (3 hours)

• 7.1 Determination of oxydation number
• 7.2 Redox at carbon
  • 7.2.1 Redox levels
  • 7.2.2 General concepts
  • 7.2.3 Reduction of carbonyl compounds, carboxylic compounds and nitriles. Complex hydrides.
  • 7.2.4 Reductive amination
  • 7.2.5 Oxidation of alcohols to carbonyl compounds or carboxylic acids
  • 7.2.6 Oxidation of alkenes: epoxydation, dihydroxylation
• 7.3 Reduction of nitro derivatives
• 7.4 Sulfur compounds. Disulfides

8) Nucleophilic substitutions at saturated carbon and eliminations (3 hours)

• 8.1 SN2 substitutions.
  • 8.1.1 General concepts. Stereospecificity
  • 8.1.2 Importance of leaving group and nucleophile
  • 8.1.3 Importance of substrate
  • 8.1.4 Influence of reaction conditions
  • 8.1.5 Competition with E2 eliminations
  • 8.1.6 Synthesis of alcohols frol alkyl halides
  • 8.1.7 Williamson synthesis of ethers
  • 8.1.8 Synthesis of amines. Azides
  • 8.1.9 Alkylation of cyanides
• 8.3 SN1 substitutions and E1 eliminations
• 8.4 Opening of epoxides

9) Natural substances (7 hours)

• 9.1 Carbohydrates
  • 9.1.1 Structure and stereochemistry of main monosaccharides
  • 9.1.2 Mutarotation
  • 9.1.3 Glycosides
  • 9.1.4 Disaccarides
  • 9.1.5 Polysaccharides
• 9.2 Lipides
  • 9.2.1 Triglycerides - waxes
  • 9.2.2 Phospholipides
• 9.3 Aminoacids and peptides
  • 9.3.1 Proteinogenic alpha-aminoacids
  • 9.3.2 Stereochemistry of aminoacids
  • 9.3.3 Acid-base properties of aminoacids
  • 9.3.4 Peptides
• 9.4) Nucleic acids

10) Outlines on radical reactions (2 hours)

• 10.1 General concepts
• 10.2 Oxygen as radical reagent
  • 10.2.1 Autooxidations.
  • 10.2.2 Cumene hydropeoxides
  • 10.2.3 Benzylic oxidations
  • 10.2.4 Autooxidation of ethers, aldehydes, unsaturated compounds
  • 10.2.5 Radical stabilizers
• 10.3 Quiniones and hydroquinones

11) ADDITIONAL LESSONS (6 ore) (only for Material Science)

• 11.1 Organometal compounds.
  • 11.1.1 Preparation
  • 11.1.2 Basic properties
  • 11.1.3 Reactions with aldehydes and ketones
  • 11.1.4 Reactions with esters, nitrile, carbon dioxide
• 11.2 Radical polymerization
• 11.3 Radical halogenation of alkanes
• 11.4 Radical benzylic and allylic halogenation
• 11.5 Synthetic applications of E2 elimination
• 11.6 Polymers
  • 11.6.1 Polyesters
  • 11.6.2 Polyamides
  • 11.6.3 "Bio-based" polymers

LABORATORY EXERCISES (16-20 hours) (from november 27 to december 18 (round 1), january (round 2), march (round 3)

1. Distillation and crystallization
2. Liquid-liquid extraction
3. Chromatography
4. Synthesis of acetylsalicylic acid
5. (Only for Material Science) Classic resolution of alpha-methylbenzylamine - polarimetry

RECOMMENDED READING/BIBLIOGRAPHY

Although no specific book will be followed, also because the module is organized by reaction type, whereas most books are organized by functional groups, students are advised to complement the slides with reading any good organic chemistry book. For example:

• W. H. Brown "Introduzione alla Chimica Organica", EdiSES
• J. McMurry "Fondamenti di Chimica Organica", Zanichelli
• J.G. Smith "Fondamenti di Chimica Organica", McGraw Hill
• L.G. Wade "Fondamenti di Chimica Organica", Piccin
• D. Klein, "Fondamenti di Chimica Organica", Pearson
• P. Y. Bruice, «Elementi di Chimica Organica», EdiSES

These books are also available in english

TEACHERS AND EXAM BOARD

Exam Board

LUCA BANFI (President)

RENATA RIVA

CHIARA LAMBRUSCHINI (Substitute)

LESSONS

LESSONS START

September 30, 2024

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The exam will be written + oral. On aulaweb students may find an accurate description of the structure of written exam and on the points attributed to each question and an exam simulation.

The written exam will be in presence, but performed as a quiz at the computer using the aulaweb platform. It will last 90 minutes, that are increased by 30% for students with SLD* and by 50% for students with disabilities.

The oral exam will follow few minutes after conclusion of the written one. It is not possible to do the oral exam in aniother session. If a students does not pass the oral exam, he/she must repeat also the written one.

The point attributed authomatically by aulaweb (maximum score = 30), will be multiplied by a factor X, which depends on the bonuses acquired, and finally rounded to the next integer (following mathematical rules). Those who have achiede at least 18 are admitted to the oral exam.

The factor X will depend on the "active attendance": 

a) For students who have passed at least 3 out of 4 intermediate quizzes, X will be = 1.15 or, if the laboratory report will be judged good, X = 1.20

b) For students who have not achieved what described at point a, but who have attended at least 2/3 of the lesssons X = 1.05

The final grade will not be an authomatic average of written and oral exam. However, If the final grade of the quiz (after multiplication for X and rounding) is 20 or less, the final mark can not be higher than 26.

During the oral exam, there will be in 3 questions (that may be only 2 in case of outstanding result of the quiz). The first one will be quite general. During the oral exam, the teacher will assess the ability of the student in writing correct formula and reaction equations and to explain the various mechanisms. One question will be on the lab or on natural substances. The third question will be more specific.

* Students who have valid certification of physical or learning disabilities on file with the University and who wish to discuss possible accommodations or other circumstances regarding lectures, coursework and exams, should speak both with the instructor and with Professor Sergio Di Domizio (sergio.didomizio@unige.it)(for Material Sciences), or Prof. Sara Ferrando (sara.ferrando@unige.it) (for Biological Sciences) the School’s disability liaison.

ASSESSMENT METHODS

Assessment will stress mainly the logical and reasoning abilities of the student, more than a notional knowledge. For this aim, the questions of the aulaweb test are conceived in order to mostly require capacity to understand formulas and logical concepts. For the same reasons, during the oral exam, the teacher will try to guide the student to the correct drawings and description, even if the student does not recall well the subject.

The written exam (quiz) and the oral exam, taken together, will allow to accurately verify the grade of achievement of the learning outcomes.

Exam schedule

FURTHER INFORMATION

Students who have valid certification of physical or learning disabilities on file with the University and who wish to discuss possible accommodations or other circumstances regarding lectures, coursework and exams, should speak both with the instructor and with Professor Sergio Di Domizio (sergio.didomizio@unige.it), the Department’s disability liaison.