Organic Chemistry Lab

1ST SEMESTER
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, with the aim to confirm the structure of the compounds obtained and to determine their purity. 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.

2ND SEMESTER
Classroom exercises (pre-laboratory): 8h
1- Brief introduction of the key concepts of NMR 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.