Organic Chemistry Lab

Goals
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 he/she will learn some procedures for the characterization of the obtained compounds, such as the measurement of the melting point and spectroscopic analysis (IR and NMR).

Acquired skills
The student will be able to:
Recognize and choose the appropriate glassware to carry out simple organic chemistry procedures.
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.



Course content

Modulo unità didattica: Laboratorio di chimica organica 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.

Modulo unità didattica: Laboratorio di chimica organica 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.

Suggested prerequisites
Modulo unità didattica: Laboratorio di chimica organica 1
It is strongly recommended that the student has passed the exam of Chimica Organica I, or at least that he/she has attended the course with continuity. The student should indeed know organic compounds nomenclature and functional groups reactivity discussed in the Chimica Organica I course, including oxidations and reductions.
Modulo unità didattica: Laboratorio di chimica organica 2
It is recommended that the student attend the laboratory module concurrently with the the Chimica Organica II course.

Reference material
Slides on course website

Prerequisites
Basic knowledge of organic chemistry


Assessment method (use at least 2 lines):
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.

Language of instruction
Italian

Attendance Policy:
Mandatory

Mode of teaching:
Traditional

Website: http://mbenaglialco.ariel.ctu.unimi.it/v1/home/Default.aspx

Course content
Selected examples of chemical transformations and functional groups conversions are presented, including reactions related to electrophilic aromatic substitution. Introduction to NMR and UV 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.