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Course, academic year 2023/2024
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Organic Chemistry II - MC270P81
Title: Organická chemie II (a)
Czech title: Organická chemie II (a)
Guaranteed by: Department of Organic Chemistry (31-270)
Faculty: Faculty of Science
Actual: from 2019 to 2023
Semester: winter
E-Credits: 5
Examination process: winter s.:
Hours per week, examination: winter s.:3/2, C+Ex [HT]
Capacity: unlimited
Min. number of students: 3
4EU+: no
Virtual mobility / capacity: no
State of the course: taught
Language: Czech, English
Note: enabled for web enrollment
Guarantor: prof. RNDr. Martin Kotora, CSc.
Teacher(s): doc. Mgr. Radim Hrdina, Ph.D.
doc. RNDr. Jindřich Jindřich, CSc.
prof. RNDr. Martin Kotora, CSc.
PharmDr. Eliška Matoušová, Ph.D.
doc. RNDr. Jiří Míšek, Ph.D.
Incompatibility : MC270P02N
Pre-requisite : MC270P80
Is incompatible with: MC270P61B
Annotation -
AIM: To expand the students' knowledge of organic chemistry and to enable them to rationalise and predict chemical reactions.
CONTENTS: A more thorough discussion of reaction types known from 1st semester of Organic Chemistry course, e.g. carbonium ion rearrangements, mechanism and stereochemistry of aliphatic nucleophilic substitution, addition and elimination reactions, and
mechanism and product distribution of aromatic electrophilic substitutions, carbonyl condensation. Natural substances.
Last update: FORSTOVA/NATUR.CUNI.CZ (05.04.2013)
Literature - Czech

1. John McMurry: Organic Chemistry, 8th ed. Brooks/Cole 2012. (Organická chemie; John McMurry; Vysoké technické učení v Brně, Nakladatelství VUTIUM a Vysoká škola chemicko-technologická v Praze; 2015.)
2. Susan McMurry: Organic Chemistry Study guide and solution manual. (Studijní příručka a řešené příklady k českému vydání učebnice John McMurry: Organická chemie; Vysoká škola chemicko-technologická v Praze; 2009.)
3. Tomáš Trnka a kol.: Organická chemie pro nechemiky, Karolinum 2002.

 

Speciální elektronické materiály nejsou k dispozici.

Last update: Matoušová Eliška, PharmDr., Ph.D. (29.07.2019)
Requirements to the exam - Czech

Požadavek pro absolvování zkoušky je úspěšné zdolání zápočtu.
Zkouška bude písemná. Bude v rozsahu učiva uvedeného v doporučené literatuře a probíraného během přednášek (vyjma spektroskopických metod).

Zápočet je možné získat po splnění minimálně 60 % zápočtového testu na konci kurzu (tj. konci semestru), zápočtový test je třeba psát u svého vyučujícího cvičení. Pro získání zápočtu je zároveň povinné vypracování deseti online testů dostupných v Moodle (zisk min. 65 % bodů z každého testu). Testy budou dostupné do konce zkouškového období. Povinné je také vypracování celkem 4 domácích úkolů a jejich odevzdání nejpozději 24 hodin před následujícím cvičením. Účast na cvičeních je povinná ze 70%, při dalších absencích je třeba dodat omluvenku nebo nebude udělen zápočet.
Počet termínů a opravných terminů se řídí zkušebním řádem.

 

 

Last update: Kotora Martin, prof. RNDr., CSc. (22.01.2024)
Syllabus -

1. Aldehydes and ketones. Synthesis of aldehydes and ketones (e.g. Friedel-Crafts reactions etc.). Oxidation of  of aldehydes and ketones (e.g. Jones oxidation). Nuclephilic additions to aldehydes and ketones: realtive reactivity, hydration, addition of HCN, addition of Grignard and organometallic reagents, additions of amines and hzdrzines, etc. 

2. Kizhner-Wolff  reaction, Clemmensen reduction, Kursanov-Parnes reduction, Mozingo reduction, formation of acetaůs and ketals, Wittig reaction, Peterson olefination, Tebbe reaction, Canizzaro reaction. Conjugoted addition to alpha,beta-unsaturated to aldehydes and ketones. (Synthetic examples: synthesis of Duloxetine, asymmetric synthesis of steroids.)

3. Carboxylic acids and nitriles. Physical properties of carboxylic acids, dissociation, effect of substitution on pKa, effect of substitution on pKa benzoic acids. Synthesis of carboxylic acids (oxidation of alcohols and aldehydes, oxidative cleavage of the double bonds, oxidation of alkyl aromatic compounds, hydrolysis of nitriles, carboxylation of Grignard and organolithium compouds, Kolbe-Schmitt raction, Willgerodt reaction, haloform reaction, Arndt-Eister reaction, Perkin reaction, malonester synthesis, Faworski rearrangement, Chemistry of nitriles. synthesis of nitriles (SN2 substitution, Sandmeyer reaction, dehydration of amides). Reactions of nitrilů (reduction, addition of water, and organometallic reagents). , adice vody, organokovových činidel).(Synthetic examples: synthesis of ibuprofen a fenclovac).

4. Functional derivatives of carboxylic acids. Nucleophilic acyl substitution. Acyl halides (synthesis, reaction: e.g. Friedel-Crafts reaction), anhydrides of carboxylic acids (preparation, reactions), carboxylic acid esters (preparation, reactions), carboxylic acid amides(preparation, reactions). Thioesters snd acylfosfonates (přírodní deriváty carboxylic acids). Polyamides and polyesters.

5. Keto-enol tautomerization (acid and base catalyzed rearrangement). Reactivity of enols and mechanism of alpha-alkylation. Alpha-halogenation of aldehydes, ketones (Faworski rearrangement) and carboxylic acids (Hell-Volhard-Zelinsky reaction). Acidity of hzdrogens in the alpha position to the carbonyl group. Reactivity of enolates: halogenation (haloform reaction), alkylation (malonester synthesis, acetoacetic synthesis). Direct alkylation of carbonyl compounds. Selenylation (formation of the double bonds).

6. Condenzation reactions of carbonyl compounds. Condenzation of aldehydes and ketones (formation of enones) and their application in organic synthesis (synthesis  of 2-ethylhexanolu). Cross aldol  condenzation (Mukaiyama aldol reaction). Intramolecular aldol condenzation. Claisen condenzation and its cross variant. Other condenzation reactions: Dieckmann reaction, Stobbe condenzation, Darzens reaction, Knoevenagel condenzation , Perkinova reaction. Michael adittion (Wieland-Mischer ketone). Stork enamin reaction. Robinson annulation.

7. Amines. Bonding in amines. Physical properties of amines. Basicity  of amines: alkylamines, arylamines, heterocyclic amines, carboxylic acid amides. Synthesis of amines (reduction of nitriles, reduction of nitro compounds, SN reactions of amines a arylamines. Sandmeyer reaction. Substitution reactions: azide synthesis, Gabriel synthesis , reductive amination, Delepin reaction). Hofmann ann Curtius degradation. Hofmanna elimination. Electrophilic aromatic substitution of arylamines. Diazonium salts (Sandmeyer reaction).

8. Saccharides. Clasification of saccharides. Stereochemistry of saccharides (Fischer projection) and their configuration. Cyklic strukture, anomers (mutarotation). Reaction of  monosaccharides: esterification, etherification (Williamson reaction, glykosides, digitoxin, Koenigs-Knorr reaction and its mechanism, methylarbatin, salicyn), reduction (alditols), oxidace (aldonic acids), chain prologation (Kiliani-Fischer synthesis) a chain degradation (Wohl degradation). Disaccharides (maltose, cellobiose, laktose, sacharose) a polysaccharides (starch, amylose, amylopektin, celulose, chitin). Deoxysaccharides, aminosaccharides,  ascorbic acid). Sweeteness and sweeteners (saccharin, aspartame, atd.).

9. Amino acids, peptides a proteins. Structure of aminoacids. Fischer projection. Isoelectric point. Synthesis of Amino acids. Peptides and proteins. Covalent bonding in peptides. Structura of peptides and its determination (Edmann and Sanger degradation). Synthesis of peptides.

10. Biomolecules and lipids. Soaps. Fosfolipids, prostagladines. Terpenoidy (isoprenoids). Steroids and their structure. Heterocyclic compounds. 5- a 6-membered heterocycles: pyrol, furan, thiofen, pyridin. Their electrophilic and nucleophilic substituttion. Nucleosides, nucleotides and nucleic acids.

 11. Pericyclic reactions. Molecular orbitals of conjugated systems and their relation to pericyclic reactions. Thermal and fotochemical electrocyklic reactions: cyclization of hexatrienes,  cyclization of dienes and ring-opening of cyclobutenes. Cykloaddition reactions: Diels-Alder reaction 2+2-cycloaddition. Sigmatropic rearrangements: 1,5- rearrangement, Cope and Claisen  rearrangement.






Last update: Kotora Martin, prof. RNDr., CSc. (21.10.2014)
 
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