C3022 Organic Chemistry II/1

Faculty of Science
Autumn 2014
Extent and Intensity
2/0/0. 2 credit(s) (fasci plus compl plus > 4). Type of Completion: zk (examination).
Teacher(s)
doc. Mgr. Kamil Paruch, Ph.D. (lecturer)
Mgr. Jakub Švenda, PhD. (lecturer)
Benoit Jean-Pierre Carbain, PhD. (assistant)
Mgr. Ondřej Hylse, Ph.D. (assistant)
RNDr. Slávka Janků, Ph.D. (assistant)
Mgr. Jaromír Literák, Ph.D. (assistant)
Guaranteed by
doc. Mgr. Kamil Paruch, Ph.D.
Department of Chemistry - Chemistry Section - Faculty of Science
Supplier department: Department of Chemistry - Chemistry Section - Faculty of Science
Timetable
Wed 9:00–10:50 B11/132
Prerequisites
C2021 Organic Chemistry I
Knowledge of General Chemistry and Organic Chemistry I
Course Enrolment Limitations
The course is also offered to the students of the fields other than those the course is directly associated with.
fields of study / plans the course is directly associated with
there are 8 fields of study the course is directly associated with, display
Course objectives
Organic chemistry of hydrocarbon derivatives. Analysis of functional groups structure and their reactivity, influence of the neighbouring skeleton upon their reactivity and opposite influence of the certain functional group upon the hydrocarbon skeleton. Sacharides, steroids and heterocyclic compounds in an overview. At the end of the course the student should understand reactivity of various functional groups and their influence upon the hydrocarbon skeleton with the final aim to deduce chemical behaviour of a complex molecule, which might be a centre of the interest.
Syllabus
  • Organic Chemistry II 1. Alkenes and alkynes. Reactivity of the nucleophilic alkenes (Organic Chemistry I). Addition of electrophiles onto alkenes and alkynes: halogenations, hydration, epoxidation, hydroboration, dihydroxylation, hydrogenation. Radical additions. Carbocation rearrangements. Preparation of alkenes and alkynes. 2. Alcohols, Thiols, Amines and their derivatives. Acidity and basicity. Nucleophilicity. Substitution / elimination and the role of leaving group (Organic Chemistry I). Preparation of alcohols (hydration, hydroboration, reduction of carbonyl compounds). Conversion of hydroxyl group into good leaving groups (halides, sulfonates) – application in substitution and elimination reactions. Amines as common organic bases. Preparation of amines (alkylation, reductive amination). Conversion of amino group into quarternary ammonium salts and N-oxides. Preparation of thiols and their oxidation to sulfoxides and sulfones. Ethers and epoxides – preparation and reactivity. Oxidation of alcohols to carbonyl compounds. 3. Aldehydes and ketones. Addition to the carbonyl group (Organic Chemistry I). Irreversible addition reactions. Organolithium and organomagnesium reagents and formation of C-C bonds. Reversible addition reactions with alcohols (hemiacetals, acetals) and amines (imines, enamines). Protecting groups. Reductive amination and Wittig reaction. 4. Enols and enolates. Keto-enol tautomerism (Organic Chemistry I). Contrast with reactivity of carbonyl group and similarities with reactivity of alkenes. Halogenation, alkylation, aldol reaction, and Mannich reaction. Synthetic equivalents of enols and enolates (enamines, enol ethers). 1,2- versus 1,4-addition. 5.Carboxylic acid derivatives. Substitution at the carbonyl group (Organic Chemistry I). Preparation of and conversion between the individual derivatives (acid chlorides, anhydrides, esters, amides). Chemoselectivity. Extension of the enolate chemistry: Claisen condensation. Common features of rearrangements: Baeyer-Villiger oxidation, Schmidt rearrangement, Curtius rearrangement, Beckmann rearrangement. 6. Aromatic compounds. Aromaticity, electrophilic and nucleophilic aromatic substitution, and substituent effects (Organic Chemistry I). Synthetic strategies for preparation of polysubstituted aromatic rings. 7. Dienes and polyenes. Conjugation and delocalization (Organic Chemistry I). Pericyclic reactions (Diels-Alder reaction, electrocyclizations, sigmatropic rearrangements). Power of transition metal chemistry: preparation of alkenes and dienes (cross-couplings, olefin metathesis). 8. Alkanes and carbenes. Radical substitution. Preparation and reactivity of carbenes: cyclopropanation and insertion into C-H bonds. 9. Organic molecules as building blocks of biological systems.
Literature
    recommended literature
  • MCMURRY, John. Organická chemie. Translated by Jaroslav Jonas. Vyd. 1. Praha: Vysoká škola chemicko-technologická v Praze, 2007. 1 sv. ISBN 9788070806371. info
  • J. Clayden, N. Greeves, S. Warren, P. Wothers. Organic Chemistry. Oxford University Press 2001
  • LITERÁK, Jaromír. Sbírka řešených příkladů k semináři z organické chemie (Collection of Excercises in Organic Chemistry). 1. vydání. Brno: Masarykova univerzita, 2012. 308 pp. ISBN 978-80-210-5810-1. info
Teaching methods
lectures with a demonstration of the taught topic on chosen examples
Assessment methods
The course is represented by a set of lectures and seminars where various phenomena are demonstrated on chosen examples. The course is closed by a written test and an oral examination.
Language of instruction
Czech
Follow-Up Courses
Further comments (probably available only in Czech)
Study Materials
The course can also be completed outside the examination period.
The course is taught annually.
Listed among pre-requisites of other courses

Zobrazit další předměty

The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 1999, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Autumn 2003, Autumn 2004, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013.
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