Subjects

Your browser does not support JavaScript, or its support is disabled. Some features may not be available.

Organic Synthesis I - MC270P13A

Title:	Organická syntéza I
Czech title:	Organická syntéza I
Guaranteed by:	Department of Organic Chemistry (31-270)
Faculty:	Faculty of Science
Actual:	from 2017
Semester:	winter
E-Credits:	4
Examination process:	winter s.:
Hours per week, examination:	winter s.:2/2, C+Ex [HT]
Capacity:	unlimited
Min. number of students:	3
4EU+:	no
Virtual mobility / capacity:	no
State of the course:	taught
Language:	Czech, English
Additional information:	http://orgchem.cz/vesely/
Note:	enabled for web enrollment

Guarantor:	prof. RNDr. Jan Veselý, Ph.D.
Teacher(s):	prof. RNDr. Jan Veselý, Ph.D.
Is pre-requisite for:	MC270P92

Opinion survey results Examination dates WS schedule

Annotation -

Last update: prof. RNDr. Jan Veselý, Ph.D. (16.06.2014)

Introduction and transformation of functional groups into the carbon skeleton: Reduction, oxidation, halogenation, nitration, nitrosation, sulfonation, metalation,diazotiasation and diazonium salt tranformation, elimination, hydroboration and reaction of boron compounds.
Formation of carbon - carbon bonds. Alkylation and acylation of carbanions and enolates, Claisen and similar condensations, Michael and similar reactions, Wittig and Peterson reactions, Friedel-Crafts alkylations and acylations, cycloaddition reactions, reactions of organometalic compounds, molecular rearrangements.

This course is for ERASMUS students also available in English.

Literature -

Last update: prof. RNDr. Jan Veselý, Ph.D. (24.10.2019)

Recommended literature:
1. Francis A. Carey, Richard J. Sundberg: Advanced Organic Chemistry, Part B - Reaction and Synthesis, Springer, 2007, ISBN: 038768350X.
2. J. Svoboda: Organická syntéza, VŠCHT Praha, 2017, ISBN: 978-80-7080-990-7.
Elektronic materials (lectures) are also available in SIS.

Other books:

Laszlo Kurti Barbara Czako: Strategic Applications of Named Reactions in Organic Synthesis, Academic Press, 2005, ISBN: 9780124297852.
Michael Smith: Organic Synthesis. Academic Press, 2011, ISBN: 9781890661403.
L. Lešetický, M. Dzurrila, P. Elečko, M. Potáček, P. Zahradník: Organická syntéza, SPN Praha, 1983.
V. Dědek, L. Lešetický, F. Liška, J. Svoboda: Organická syntéza. Transformace funkčních skupin. Karolinum, Praha 1995.

Requirements to the exam -

Last update: prof. RNDr. Jan Veselý, Ph.D. (24.10.2019)

Requirements for study control:

credit - oral presentation about selected synthetic organic method
exam - first part (written part with score above 60%), second part (oral)

Syllabus -

Last update: SMRCEK (29.01.2003)

Part A. Introduction and transformation of the functional groups

1. Introduction. Scope and limitation of this course. Basic definitions. Carbon skeleton. Functional group. Literature sources.

2. Reduction. Clasification, basic mechanisms, sterreochemistry. Catalytic hydrogenation and hydrogenolysis, reduction by metals and electic current, reductions by complex hydrides, reductions by other reagents. Reduction of the different functional groups.

3. Oxidation. Basic kinds of the oxidation reactions, mechanisms, selectivity. Overview of the reagents. Oxidation of the different functional groups.

4. Halogenation. Overview of the reagents, mechanisms and stereochemistry. Electrophilic halogenation of aromates. Electrophilic halogenation of alifatic substrates. Nucleophilic alifatic substitution. Addition reactions.

5. Nitration, nitrosation, sulfonation. Electophilic nitration of aromatic compounds. Nitration and nitrosation of alifatic compounds. Sulfonation of aromatic substrates. Alifatic nucleophilic substitution.

6. Functional interconversions in carbonyl and carboxyl groups. Enolates and enolethers. Acetals and orthoesters. Schiff bases. Enamines. Oximes, hydrazones. Carboxylic esters. Amides, amidines. Acylazides acylhydrazides. Hydroxamic acids.

7. Organometalic compounds. Substitution of hydrogen by metal. Substitution of functional group (halogen) by metal. Transmetalation. Alcali metal compounds, Grignard reagents, Compounds of Zn, Cd, Hg. Organocopper reagents. Transition metal compounds.

8. Diazotisation and reactions of diazonium salts. Diazotisation methods. Substitution of the diazonium group by nucleophilic reagents. Copulation of diazoniun salts with aromatic compounds, with alifatic compounds.

9. Elimination reactions. Mechanisms and stereochemistry. Eliminations of oxygen functional groups. Eliminations of nitrogen functional groups. Eliminations of halogens. Eliminations of sulfur functional groups. Decarboxylation and decarbonylation.

10. Hydroboration and reactions of boron compounds. Hysdrfoboration. Isomeration of boranes. Hydrolysis, halogenation of boranes. Syntheses of alkenes and dienes. Oxidation. Carbonylation.