Organic chemistry lab

A.Y. 2018/2019
10
Max ECTS
160
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
The aim of the present course is to introduce the student to the main experimental procedures in Organic Chemistry (extraction, crystallization, chromatographic techniques, distillation), allowing him to perform synthetic sequences, isolating and purifying the products. The student will be trained to operate appropriately and independently in a laboratory of organic chemistry. In order to pursue this goal, the experimental work will be developed individually by any student.
Expected learning outcomes
At the end of the laboratory, students will acquire a basic familiarity with the practical operations of experimental Organic Chemistry, and the capability to correctly evaluate the purity of isolated products.
Course syllabus and organization

Single session

Lesson period
year
Unit: Laboratory of organic chemistry 1
Course syllabus
Goals
The aim of the present course is to introduce the student to the main experimental procedures in Organic Chemistry (extraction, crystallization, chromatographic techniques, distillation), allowing him to perform synthetic sequences, isolating and purifying the products. The student will be trained to operate appropriately and independently in a laboratory of organic chemistry. In order to pursue this goal, the experimental work will be developed individually by any student.

Acquired skills
At the end of the laboratory, students will acquire a basic familiarity with the practical operations of experimental Organic Chemistry, and the capability to correctly evaluate the purity of isolated products.

Course content
TEACHING UNIT: LABORATORY OF ORGANIC CHEMISTRY, I
Classroom exercises (pre-laboratory): 16h
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 and mp.
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.

TEACHING UNIT: LABORATORY OF ORGANIC CHEMISTRY, II
Classroom exercises (pre-laboratory): 16h
1- Brief review of the key concepts of IR 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
· Autan 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.

Suggested prerequisites
To have attended the General Chemistry and Organic Chemistry I course; to have attended or attend the Organic Chemistry II course. It is mandatory to have attended the first module of the Organic Chemistry Laboratory to be admitted to the second module.

Reference material
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.


Prerequisites
Knowledge of the basic principles of Organic Chemistry.


Assessment method
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.

Language of instruction
Italian

Attendance Policy:
Obligatory


Mode of teaching:
Traditional

Website:
https://lraimondiapuglisilcoa.ariel.ctu.unimi.it/v5/home/Default.aspx
Unit: Laboratory of organic chemistry 1
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Practicals: 16 hours
Laboratories: 64 hours
Shifts:
Corso A
Professor: Raimondi Laura Maria
Corso B
Professor: Puglisi Alessandra
Unit: Laboratory of organic chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Practicals: 16 hours
Laboratories: 64 hours
Professors: Lay Luigi, Lesma Giordano
Shifts:
Professor: Lesma Giordano
Corso A
Professor: Lesma Giordano
Corso B
Professor: Lay Luigi
Professor(s)
Reception:
please contact by e-mail or phone
Dipartimento di Chimica - via Golgi 19 - Milano - building C, 2nd floor, room 2011 or via Teams