Organic chemistry

A.Y. 2021/2022
6
Max ECTS
56
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
The course aims to provide the basic knowledge to be able to deal with specific chemical, biochemical and professional courses
of the degree course with rigor and scientific method, through lectures and classroom exercises (unit-1) and laboratory activities
(unit -2).
Unit-1 The objective is to learn how to classify organic compounds on the basis of the functional group that characterizes them.
The student will learn to write the formula and structure of organic compounds, including biomolecules such as amino acids,
polysaccharides and lipids. Furthermore, by correlating the structure to the reactivity, he will learn the main chemical reactions
that allow to transform and functionalize the organic compounds themselves. The study of all organic chemical reactions will
find its maximum application in the design of multistep synthesis of more complex organic compounds.
Unit-2 The objective is to deepen the topics covered through practical exercises in the laboratory. The student will learn the
main analytical techniques (extraction, distillation, acid-base separations and chromatography) to purify organic compounds
from mixtures of several products.
Expected learning outcomes
At the end of the course the student must have acquired the basics to recognize, face and overcome some fundamental
problems related to Organic Chemistry.
In particular, the student must be able to write the formula, the structure of organic compounds, including biomolecules such
as proteins, carbohydrates, lipids and know their chemical-physical properties. He must be able to indicate through reaction
schemes the main characteristic reaction mechanisms for each compound, thus correlating the molecular structure and the
functional group to reactivity. Furthermore, he must be able to design multistep syntheses of more complex organic molecules.
Being able to carry out a multistep synthesis consists in demonstrating the capacity of autonomy in mastering the program and
the capacity of judgment in being able to choose among the numerous reaction conditions studied the most selective ones to
make the transformations take place. After having participated in the laboratory activities, the student must show critical and
judgment skills by recognizing and applying analytical methods (extraction, distillation, chromatography, acid-base separation)
to purify organic compounds from mixtures of several products. Finally, the student must be able to explain all the course
contents in a clear and logical way, also orally.
Course syllabus and organization

Single session

Lesson period
Second semester
The lectures will be carried out partly in person and partly online (using the Microsoft Teams platform), according to the published calendar and the indications
given by the University. The lessons will be recorded and made available on the Ariel website. The exercises aimed at preparing the exam will take place online, partly asynchronously (providing the material on the Ariel website) and partly with synchronous mode to give the student the opportunity to propose exercises to be solved together with the intent of clarify any doubts (through the Microsoft Teams platform). The laboratory exercises will be carried out regularly in the presence, scrupulously following the rules set by the University and those who cannot be present will be able to follow the development of the experiment in synchrony through the Microsoft Teams platform.
Information on the organization of lessons and how to access Microsoft Teams and any other information on teaching will be available on the ARIEL website
teaching: it is therefore recommended to consult it regularly. Based on the evolution of the epidemic and in compliance with the relevant regulations, they will be able to
modify the modalities of the activities planned in the classroom, informing the students through ARIEL. The course program will not change. The exam methods will consist of a written and an oral one through the Microsoft Teams platform.
Course syllabus
Organic compounds: structure, properties, functional groups; carbon hybridization in organic compounds, chemical equilibria between organic compounds.
Alkanes and cycloalkanes: conformational analysis; chemical-physical properties; radical halogenation reaction.
Alkenes: structure, properties, geometric isomerism.
Alkenes: electrophilic double bond addition reactions according to Markovnikov and anti Mark.
Aromatic compounds: structure, nomenclature, benzene and aromatic electrophilic substitutions. Halogen derivatives of hydrocarbons: structure, properties
SN1 and SN2
Alcohols: structure, properties, and reactivity
Phenols: structure, acidity, Other oxygenated derivatives: ethers,
Chirality and optical activity; absolute configuration of stereogenic centers
Enantiomers and diastereoisomers; racemes.
Aldehydes and ketones: structure, properties; oxidoreduction and nucleophilic addition reactions to carbonyl.
Aldehydes and ketones: addition of nitrogen nucleophiles and Grignard reagents.
Aldehydes and ketones: keto-enolic tautomerism
Carboxylic acids: properties, acid-base reactions
Carboxylic acid derivatives: esters, amides, anhydrides, acyl chlorides
Acyl substitution reactions: Fisher esterification; hydrolysis of esters and amides
Basic and acid hydrolysis of esters
Amines: structure, properties, basicity, reactivity, imines,
Amino acids; the peptide bond; peptides and proteins
Sugar structure, mutual rotation phenomenon, reduction and oxidation reactions
Lipids: fatty acids, glycerol, triglycerides functions and structure
Saponification reaction
Prerequisites for admission
Knowledge acquired during the General and Inorganic Chemistry course
Teaching methods
Lectures, exercises and slides projection in classroom and the use of the Kahoot program on tablets or smartphones. Before each ongoing test, a simulation will be performed in the classroom through the resolution of exercises by the teacher.
Laboratory experiences will take place between April and June, e.g. extraction of lavender essential oil from lavender flowers, extraction of lycopene from tomato, dosage of caffeine in energy drinks, preparation of soap, distillation of benzoic acid and vanillin.
Teaching Resources
Text book: Introduzione alla Chimica Organica di W. Brown, T. Poon, Casa Editrice EdiSES. Notes from lessons, textes and solutions of exam texts are available at http://ariel.unimi.it.
Alternatively we recommend the use of any other organic chemistry text for university students
Assessment methods and Criteria
During the Organic Chemistry course, two written tests are scheduled; the first will take place halfway through the course, the second, the first week after the end of the course. Only students who have passed the first test with a mark greater than or equal to 18 can access the second test. To pass the exam, both tests must be sufficient, i.e. each passed with a mark greater than or equal to 18. The final mark will consist of the mathematics average of the two marks obtained in each ongoing test. Oral interview is not carried out. The ongoing tests are not mandatory and require registration. The typology of exam tasks consists of a variable number of exercises according to the examples shown during the classroom exercises. For those who do not pass the ongoing tests and for those who decide a priori not to participate, the exam will consist of a single written test on the dates set within each exam session. The single test will consist of a variable number of exercises on the entire program.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Practicals: 16 hours
Lessons: 40 hours
Educational website(s)