Organic chemistry lab

A.Y. 2021/2022
10
Max ECTS
144
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. 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

Responsible
Lesson period
year
Laboratory of Organic Chemistry I
The activity will be shift-based, but each shift will be reduced to approximately 5-7 days depending on the number of students and rules for laboratory occupancy.
Classroom lectures: 8 hours online in synchronous mode (that subsequently will
be available in asynchronous mode)
Pre-laboratory lectures will be carried out in presence (if possible)
The laboratory chemical manipulations will be carried out in presence, but their number will be reduced owing to the reduced duration of the shifts:
1. Separation of two organic compounds by means of selective liquid-liquid extraction, purification by crystallization, evaluation of their purity grade (TLC and m.p.) and spectroscopic characterization (IR).
2. Separation by column chromatography and characterization of the isolated compounds by IR spectroscopy.
3. Aldehyde reduction, with isolation and spectroscopic characterization of the obtained compound.
4. Chemical synthesis of Aspirin (acetylsalicylic acid), followed by isolation and spectroscopic characterization of the compound.
Videotapes of all laboratory chemical manipulations will be carried out and made available for download to students who will attend the laboratory course online. Production of detailed reports (laboratory book format) related to each laboratory chemical manipulation, however, is mandatory for all students, regardless of their attendance mode.
After each laboratory shift there will be an examination (in synchronous mode) consisting of one numerical excercise and one theoretical question (four theoretical questions for students who attended the course remotely, so that there will be a homogeneous evaluation with the students who attended the course in presence).
The Laboratory of Organic Chemistry II, scheduled in the 2nd semester starting from March 2022, will take place according to traditional methods (see next tabs for a more detailed description), unless otherwise indicated by the academic authorities.
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).
Assessment methods and Criteria
Practical: 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 i) to accept the proposed score, or ii) 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 may entail an increase/decrease of the rating up to a maximum of ±2 points.
Unit: Laboratory of organic chemistry 1
Course syllabus
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.
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.
Unit: Laboratory of organic chemistry 2
Course syllabus
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.
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.
Unit: Laboratory of organic chemistry 1
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Shifts:
Corso A
Professor: Puglisi Alessandra
Corso A + B
Professor: Raimondi Laura Maria
Corso B
Professor: Raimondi Laura Maria
Unit: Laboratory of organic chemistry 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Laboratories: 64 hours
Lessons: 8 hours
Shifts:
Corso A
Professor: Lay Luigi
Corso A + B
Professor: Lay Luigi
Corso B
Professor: Pignataro Luca Luigi
Educational website(s)
Professor(s)
Reception:
Thursday from 10:30 to 12:30
Room 2042, second floor of the Chemistry building (Corpo B)
Reception:
please contact by e-mail or phone
Dipartimento di Chimica - via Golgi 19 - Milano - building C, 2nd floor, room 2011 or via Teams