Innovative methods for synthesis and analysis

A.Y. 2019/2020
Overall hours
Learning objectives
- Offer more in-depth knowledge of organic chemistry.
- Give the appropriate skills to solve more complex synthetic processes.
- Knowledge of modern synthetic methods using selective reagents of new generation.
- Give the appropriate skills to work independently in a research lab of organic chemistry.
- Knowledge of the more important analytic methods used in organic synthesis lab
- Knowledge and use the most important database for organic chemists (Scifinder)
Expected learning outcomes
- Advanced knowledge of synthetic organic chemistry.
- Skills in the development of complex reaction patterns by identifying by analyzingthe problems related to the presence of different functional groups and to the stereochemical aspects of a reaction
- Use of acquired skills to tackle experimental thesis
Course syllabus and organization

Single session

Lesson period
Second semester
Prerequisites for admission
Theoretical course:
Good knowledge of organic chemistry I and II
Basic knowledge of synthetic techniques acquired in a laboratory of organic synthesis
Assessment methods and Criteria
Theoretical course: written exam relating to the synthesis of organic compounds (10 exercises; marks for each exercise: 0-3) followed by discussion of the results.
Laboratory module: evaluation of the laboratory activity and of the report delivered by the student
The final mark is the result of the weight average of the mark of the written exam and of the laboratory activity.
Innovative methodologies for synthesis and analysis. Mod. 1
Course syllabus
A) The chemistry of protecting group:Protection of alchools, amines, thiols, carbonyl compounds, carboxylic acids. Othogonal protection; DNA synthesis: an example of the use of protecting groups
B) Cycloaddition reactions: i) regio- diastereo- and enantioselective Diels-Alder reactions ii) 1,3-dipolar cycloadditions
C) C-C bond formations: i) regio- and stereoselective alkylation of aldehydes, ketones and esters ii) enantioselective alkylation of ketones via enamines iii) stereoselective aldol condensations iv) stereoselective condesation between esters and carbonyl compounds
D) Reduction: i) Use of regio- diastereo- and enantioselective reagents for the reduction of olefins, carbonyl and carboxylic acid derivatives ii) Hydroboration reaction and use or boranes in the reductive processes
E) Use of organometallic compounds in organic synthesis i) reaction involving transition metals (Pd, Rh, Ru) ii) C-C-bond formation by using organoboranes, organotin and zinc halides iii) Pd-catalyzed carbonylation
Teaching methods
classroom lectures with explanation of the various course topics, followed by interactive exercises on organic synthesis
Teaching Resources
- Course slides available on Ariel
- recommended textbooks listed in the first slides of the course
- examples of written tests on the Ariel website
Innovative methodologies for synthesis and analysis. Mod. 2
Course syllabus
The practical activities are listed below:
1. on-line bibliographic researchers regarding the products to be synthesized
2. synthesis of reagents and products exploiting different particular techniques related to: a) use of techniques for reactions under inert atmosphere and anhydrous solvents; b) use of reagents sensible to wet and air
3. use of gas-chromatography
4. use of polarimetry
6. identification of suitable analytical procedures (e.g. MS and NMR spectroscopic analyses) aimed to structural determination and characterization of different products synthesized
Teaching methods
Practical experiences in advanced organic synthesis laboratory and computer laboratory practice.
Teaching Resources
List of synthetic procedures for the synthesis of specific compounds
Innovative methodologies for synthesis and analysis. Mod. 1
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
Lessons: 32 hours
Professor: Gelmi Maria Luisa
Innovative methodologies for synthesis and analysis. Mod. 2
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
Single bench laboratory practical: 64 hours