Organic chemistry lab
A.Y. 2020/2021
Learning objectives
The aim of the present course is to introduce the student to the main experimental procedures in Organic Chemistry. In order to pursue this goal, the experimental work will be developed individually by each student. Particular care will be devoted to safety rules. The student will learn the main techniques for the isolation and purification of organic compounds. The student will be also introduced to some basic organic reactions, and will learn some procedures for the characterization of the obtained compounds.
Expected learning outcomes
The student will be able to: carry out the routine operations in an organic chemistry lab, paying special attention to the safety aspects (filtration, phase separation, crude reaction mixture isolation, acidic and basic work up, TLC analysis, purification through crystallization, distillation or column chromatography); make adeguate choices with regard to reaction conditions; apply some spectroscopic techniques to solve structural problems for simple organic compounds.
Lesson period: year (In case of multiple editions, please check the period, as it may vary)
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Course syllabus and organization
Single session
Responsible
Lesson period
year
Module II of the laboratory will be in the second semester and will take place regularly in attendance, as in previous years. If it is not possible, and it is necessary to foresee an occupation of the laboratories according to spacing rules, we will adjust as in the first module (see below), with a reduced number of experiences. In case of total closure and inability to attend in presence, the course will take place as in the A.Y. 2019-20, only online, through material (audio video films, presentations and articles) uploaded on the Ariel website of the course.
Module 1 of the Organic Chemistry laboratory will take place in the presence of shifts (5-7 days depending on the total number of students involved and the indications received on the occupation of the laboratories).
· Frontal lessons: 8 hours online synchronously (subsequently usable asynchronously)
· first frontal lesson Friday 2 October 2020 (still to be determined whether morning or afternoon)
· Pre-workshops possibly carried out in presence
· The experiences carried out in presence will be less than usual due to the shorter duration of the shifts:
1. a separation of two substances by selective extraction, purification by crystallization, evaluation of purity (TLC and p.f.) and spectroscopic characterization (IR)
2. a chromatographic separation with IR characterization of the compounds
3. a reduction of an aldehyde with product isolation and spectroscopic characterization
4. the synthesis of aspirin with isolation and purification by crystallization.
· For students who will use the laboratory course remotely, the experiences will be filmed and left available asynchronously. They too will have to produce the reports / extract from the laboratory notebook of each experience
· At the end of each shift there will be an exam carried out synchronously with a numerical exercise and one theory question (4 theory questions for students who attend remotely, to allow a homogeneous assessment compared to the direct observation of those who have attended in presence).
Module 1 of the Organic Chemistry laboratory will take place in the presence of shifts (5-7 days depending on the total number of students involved and the indications received on the occupation of the laboratories).
· Frontal lessons: 8 hours online synchronously (subsequently usable asynchronously)
· first frontal lesson Friday 2 October 2020 (still to be determined whether morning or afternoon)
· Pre-workshops possibly carried out in presence
· The experiences carried out in presence will be less than usual due to the shorter duration of the shifts:
1. a separation of two substances by selective extraction, purification by crystallization, evaluation of purity (TLC and p.f.) and spectroscopic characterization (IR)
2. a chromatographic separation with IR characterization of the compounds
3. a reduction of an aldehyde with product isolation and spectroscopic characterization
4. the synthesis of aspirin with isolation and purification by crystallization.
· For students who will use the laboratory course remotely, the experiences will be filmed and left available asynchronously. They too will have to produce the reports / extract from the laboratory notebook of each experience
· At the end of each shift there will be an exam carried out synchronously with a numerical exercise and one theory question (4 theory questions for students who attend remotely, to allow a homogeneous assessment compared to the direct observation of those who have attended in presence).
Course syllabus
Module 1 (5 cfu)
1. Safety and accident prevention in the chemical laboratory
2. Main techniques for the isolation and purification of organic compounds (extraction, crystallisation, simple and fractional distillation, chromatography)
3. Introduction to IR spectroscopy
4. Experimental aspects of some fundamental organic reactions (oxidations, reductions, condensations, nucleophilic substitutions, Fischer synthesis), evaluation of the purity grade of the obtained products through TLC and melting point measurement
5. The experimental activities performed in the laboratory aim at applying the topics discussed in classroom.
Module 2 (5 cfu)
Selected examples of chemical transformations and functional groups conversions are presented, including reactions related to electrophilic aromatic substitution. Introduction to NMR spectroscopy. The experimental activities developed in the organic chemistry laboratory are aimed at applying the topics discussed in classroom:
the synthesis of an amide of an aromatic carboxylic acid, an example of aromatic heterocycle synthesis, a two steps reaction sequence for the preparation of a substituted aniline, the use of diazonium salt in the preparation of an indicator, a phase transfer-catalyzed transformation.
Finally the determination of an unknown carbonyl compound, the separation of a mixture of two unknown compounds, their recognition and preparation of their suitable derivatives are the topics of the last week in lab.
The characterization of the products will be accomplished by melting point, TLC analysis, IR and NMR spectroscopy.
The common purification techniques for organic compounds are employed: crystallization, acid/base separation, distillation under vacuum, chromatographic separation on a silica gel column.
1. Safety and accident prevention in the chemical laboratory
2. Main techniques for the isolation and purification of organic compounds (extraction, crystallisation, simple and fractional distillation, chromatography)
3. Introduction to IR spectroscopy
4. Experimental aspects of some fundamental organic reactions (oxidations, reductions, condensations, nucleophilic substitutions, Fischer synthesis), evaluation of the purity grade of the obtained products through TLC and melting point measurement
5. The experimental activities performed in the laboratory aim at applying the topics discussed in classroom.
Module 2 (5 cfu)
Selected examples of chemical transformations and functional groups conversions are presented, including reactions related to electrophilic aromatic substitution. Introduction to NMR spectroscopy. The experimental activities developed in the organic chemistry laboratory are aimed at applying the topics discussed in classroom:
the synthesis of an amide of an aromatic carboxylic acid, an example of aromatic heterocycle synthesis, a two steps reaction sequence for the preparation of a substituted aniline, the use of diazonium salt in the preparation of an indicator, a phase transfer-catalyzed transformation.
Finally the determination of an unknown carbonyl compound, the separation of a mixture of two unknown compounds, their recognition and preparation of their suitable derivatives are the topics of the last week in lab.
The characterization of the products will be accomplished by melting point, TLC analysis, IR and NMR spectroscopy.
The common purification techniques for organic compounds are employed: crystallization, acid/base separation, distillation under vacuum, chromatographic separation on a silica gel column.
Prerequisites for admission
Basic knowledge of organic chemistry
Teaching methods
Traditional
Attendance : mandatory
Attendance : mandatory
Teaching Resources
Slides on course website
Course web site: http://mbenaglialco.ariel.ctu.unimi.it/v1/home/Default.aspx
Course web site: http://mbenaglialco.ariel.ctu.unimi.it/v1/home/Default.aspx
Assessment methods and Criteria
Practical (an additional oral assessment is possible upon request of the student). The evaluation will consider both the experimental activities developed individually by each student and the final test, with the aim to verify the skills acquired by the student and his/her ability to work with confidence in a laboratory of Organic Chemistry, and in compliance with the safety rules. Based on the content of the written reports (prepared by the student and describing each experimental activity), the oral assessment will be about the different subjects presented during the course.
Unit: Laboratory of organic chemistry 1
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Lessons: 8 hours
Professors:
Belvisi Laura, Sattin Sara
Shifts:
Professors:
Belvisi Laura, Sattin Sara
Corso A
Professor:
Sattin SaraCorso B
Professor:
Belvisi Laura
Unit: Laboratory of organic chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Lessons: 8 hours
Shifts:
Professor:
Silvani Alessandra
Corso B
Professor:
Silvani AlessandraEducational website(s)