ORGANIC CHEMISTRY APPLIED

Degree course: 
Corso di First cycle degree in Chemical Sciences and Technologies
Academic year when starting the degree: 
2014/2015
Year: 
3
Academic year in which the course will be held: 
2016/2017
Course type: 
Supplementary compulsory subjects
Credits: 
6
Period: 
First Semester
Standard lectures hours: 
60
Detail of lecture’s hours: 
Lesson (60 hours)
Requirements: 

The contents of the courses of Organic Chemistry I and Organic Chemistry II are prerequisiti.

Assessment: 
Voto Finale

The main targets of the course are the following:
1)To provide a general view of the oxidation and reduction methods of the main functional groups focusing expecially on the chemoselective reactions and, if possible, on the stereo- and enantioselective versions.
2)To experiment some of the reactions shown in the theoretical course in order to verify their efficiency and to face the experimental issues involved.
At the end of the course the students will have become familiar with the oxidation and reduction reactions and will be able to use them in the planning of organic synthesis.

The course is divided in two theoretical and one experimental modules.
1) Oxidation reactions
•Alcohol oxidation: Jones reagent, PCC, PDC, Ley, Moffat, Swern, and Dess-Martin oxidations, Fetizon oxidation, allylic alcohol oxidationi.
•Oxidation of carbonylic compounds to carboxylic acids
•Oxidation of carbonylic compounds to 1,2-carbonylic compounds.
•Oxidation of ketones to esters: Bayer-Villiger reaction
•Oxidation of phenols
•Oxidation in the allylic position.
•Double bond oxidation: epoxidation with peracids, alkylhydro peroxides and hydroperoxides. Asymmetric epoxidation: Sharpless, Shi and Jacobsen-Katsuki
•Oxidation of alkenes to 1,2-diols cis and trans
•Oxidation of heteroatoms: nitrogen, sulfur and selenium
2) Reduction reactions
•Heterogeneous and homogeneous catalytic hydrogenation
•Transfer hydrogen reaction.
•C=C reduction with I group metals in NH3
•Reduction of aromatic compound: Birch reaction
•C=N reduction
•Reduction of carboxylic acids and derivatives
•Reduction of carbonyl compounds. Enantioselective reductions of ketones
•Reduction of C-O and C-N bonds

Francis A. Carey, R. J. Sundberg “Advanced Organic Chemistry” Part B

Final exam: written resolution of exercises, oral discussion of theoretical questions and evaluation of laboratory reports

Professors