Organic chemistry lab

A.Y. 2019/2020
Overall hours
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. He/she will illustrate what has been done in the laboratory with written reports.
Course syllabus and organization

Single session

Course syllabus
Laboratory of Organic Chemistry, I
Classroom exercises (pre-laboratory): 8h
1- Safety and accident prevention in the chemical laboratory.
2- Main techniques of isolation and purification of organic compounds (extraction, crystallization, simple distillation, fractional distillation, chromatography).
3- Introduction to IR spectroscopy.
4- Experimental aspects of some fundamental organic reactions and evaluation of the purity grade of the obtained products through TLC.
Laboratory Chemical Manipulations: 64 hrs
Practical execution of separation and purification procedures of organic compounds (extractions, crystallization, chromatography, distillation) and of simple organic reactions referring to the reactivity of functional groups. In particular, oxidations of alcohols, reduction of carbonyls, esterifications and aldol condensations will be performed. The students will learn also to prepare samples for IR spectroscopy and to register IR spectra. At the end of the laboratory, students will have to demonstrate at least a basic familiarity with the practical operations of experimental organic chemistry, and capability to correctly evaluate the purity of isolated products.

Laboratory of Organic Chemistry, II
Classroom exercises (pre-laboratory): 8h
1- Brief introduction of the key concepts of NMR and UV spectroscopy and their utilization for the determination of the structure of compounds prepared in laboratory.
2- Analytical and preparative chromatography from an applicative point of view.
3- Evaluation of reaction parameters, such as: right choice of the solvent, temperature, order of the addition of reagents, etc.
4- Functionalization reactions of aromatic compounds referring to the multistep synthetic syntheses to be performed.
Laboratory Chemical Manipulations: 64 hrs
Practical execution of simple multistep synthesis sequences referring to the chemistry of aromatic compounds. All of the experiences are "single bench".
In particular, aromatic electrophilic and nucleophilic reactions, diazotation, Sandmeyer, Michael 1,4-addition are carried out.
In addition several small molecules are synthesized:
· 1-phenyl-3-phenylaminopyrrolidin-2,5-dione
· Synthesis of a bioactive principle
· 2,4-dinitrophenyl-2'-naphtyl ether
· para-nitroacetanilide, and its conversion into para-nitro aniline
· p-iodonitrobenzene
The main organic functional groups will be identified by both spectroscopic methods and the study of their reactivity through the preparation of selected derivatives.
Mixture of unknown compounds, different for each student, will be separated, and the components purified and characterized. Products belong to the classes of: primary, secondary and tertiary amines; aldehydes, ketones , carboxylic acids, ethers, halo and nitro derivatives, hydrocarbons.
Mixtures will be separated by column chromatography and through the acid-base separation.
Prerequisites for admission
Attendance of General and Inorganic Chemistry and Organic Chemistry I courses. Attendance (also ongoing) of Organic Chemistry II course. Attendance with a positive evaluation (not less than 18/30) of the first module of Laboratory of Organic Chemistry (mandatory for admission to the second module).
Teaching methods
Classroom lectures: pre-laboratory
Laboratory Chemical Manipulations
Teaching Resources
Suggested reference books:
- M.D. Ischia: La Chimica Organica in Laboratorio, Piccin, Padova, 2002;
- B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell: Vogel's Textbook of Practical Organic Chemistry, Longman Group, UK Limited, 1989;
- D.L. Pavia, G.M. Lampman, G.S. Kriz: Il Laboratorio di Chimica Organica, Edizioni Sorbona, MI, 1994.
Assessment methods and Criteria
practical and oral
Due to the experimental nature of the course, the examination will be based on the practical results obtained in the lab as well as on the required reports. The score (maximum 30/30), will represent the average of the evaluations of the two session of practical experiences. The student will have the possibility to sustain an oral examination in order to improve the score. The oral examination will be focused on all the topics treated during the course, with attention to the practical experiences performed in the lab. The oral examination not necessarily implies an improvement of the rating.
Unit: Laboratory of organic chemistry 1
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Corso A
Professor: Raimondi Laura Maria
Corso A+B
Professor: Puglisi Alessandra
Corso B
Professor: Puglisi Alessandra
Unit: Laboratory of organic chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Corso A
Professors: Arosio Daniela, Lay Luigi, Polito Laura
Corso A+B
Professor: Lay Luigi
Tuesday from 10:30 to 12:30
Room 2025, second floor of the Chemistry building (Corpo B)
please contact by e-mail or phone
Dipartimento di Chimica - via Golgi 19 - Milano - building C, 2nd floor, room 2011