C3050 Organic Chemistry II

Faculty of Science
autumn 2017
Extent and Intensity
4/0/0. 4 credit(s) (plus extra credits for completion). 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)
Mgr. Václav Němec, 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
Mon 18. 9. to Fri 15. 12. Mon 9:00–10:50 B11/132, 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
Course objectives
During the course the students will be acquainted with chemistry of hydrocarbons derivatives, their structure assessment and reactivity of different functional groups, their influence on the reactivity of the hydrocarbon skeleton and vice versa. More complex molecules, e.g. saccharides, steroids and heterocyclic compounds, will be also covered. The main aim of the course is to provide understanding of the structure of single functional groups and their behaviour in combination with the character of the hydrocarbon skeleton, and evaluation of the chemical properties of complex molecules.
Learning outcomes
Students will be able to assess structure and reactivity of common functional groups and thus they will be able to evaluate chemical properties of basic types of organic molecules.
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
  • CLAYDEN, Jonathan. Organic chemistry. 2nd ed. Oxford: Oxford University Press, 2012, xxv, 1234. ISBN 9780199270293. info
  • 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 demontration of the taught topic on chosen examples
Assessment methods
There are 3 written tests during the semester. The final examination consists of a written test with maximum 100 points (minimum 50 points is required to pass).
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
The course is also listed under the following terms Autumn 1999, Autumn 2000, Autumn 2001, Autumn 2002, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.
  • Enrolment Statistics (autumn 2017, recent)
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