Organic Chemistry II - GAF299

• Title: Organic Chemistry II
• Guaranteed by: Department of Organic And Bioorganic Chemistry (16-16120)
• Faculty: Faculty of Pharmacy in Hradec Králové
• Actual: from 2024
• Semester: summer
• Points: 0
• E-Credits: 5
• Examination process: summer s.:combined
• Hours per week, examination: summer s.:28/20, C+Ex [HS]
• Capacity: unlimited / 60 (unknown)
• Min. number of students: unlimited
• 4EU+: no
• Virtual mobility / capacity: no
• State of the course: taught
• Language: English
• Teaching methods: full-time
• Note: deregister from the exam date if a requisite was not fulfilled; course can be enrolled in outside the study plan; enabled for web enrollment
• Guarantor: doc. Dr. Russell Richard Anthony Kitson
• Co-requisite : GAF390, GAF391
• Incompatibility : GAF133, GAF292
• Interchangeability : GAF133, GAF292
• Is co-requisite for: GAF243, GAF229, GAF050
• Is pre-requisite for: GAF141, GAF300, GAF244, GAF341
• Is interchangeable with: GAF133

Annotation

English

Preparatory discipline for profile subjects taught at the Faculty of Pharmacy. Themes: System of organic compounds: hydrocarbons, halogen derivatives, alcohols, phenols, ethers, amines, sulfur and silicon compounds, carbonyl compounds, carboxylic acids and their derivatives, substituted carboxylic acids and their derivatives, carbonic acid derivatives, organometallic compounds.

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Czech

Průpravná disciplina pro výuku profilových disciplín vyučovaných na fakultě. Témata: Systém organických sloučenin: uhlovodíky, halogenderiváty, alkoholy, fenoly, ethery, aminy, sloučeniny síry a křemíku, karbonylové sloučeniny, karboxylové kyseliny a jejich deriváty, substituované karboxylové kyseliny a jejich deriváty, deriváty kyseliny uhličité, organokovové sloučeniny, heterocykly

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Course completion requirements

English

The condition to obtain the credit is 100% attendance at the seminars and at least 60% points from tests written during the semester or from credit test. Exam has written test (minimum 60% points) and oral part.

2 Exam Questions: 

Drug formula, its name, physical and chemical properties

System: 

1.    Alkanes, cycloalkanes, nomenclature, synthesis, reactivity

 

2.     Alkenes, nomenclature, preparation (Zaitsev´s rule), reactivity (Markovnikov´s rule and anti-Markovnikov´s rule), reactivity

 

3.    Dienes, polyenes, Diels-Alder reaction, Alkynes, nomenclature, preparation and reactivity

 

4.    Benzene, aromaticity of compounds, electrophilic aromatic substitution, effect of substituents on electrophilic aromatic substitution

 

5.    Nucleophilic aromatic substitution.

 

6.    Alkylhalides, nomenclature, preparation, reactivity of halogenalkanes (substitution, elimination, comparison with arylhalogenates)

 

7.    Alcohols, ethers, nomenclature, preparation, reactivity

 

8.    Aldehydes, ketones, nomenclature, synthesis, reactivity

 

9.     Reaction of aldehydes and ketones with N-bases, O-bases and S-bases, Haloform reaction, oxidation reduction of carbonyl compounds

 

10. Reactivity of carbonyl compounds with C-H acids, Aldol and Crossed Aldol reactions (α-carbon)

 

11. Carboxylic acids, nomenclature, preparation and their reactivity

 

12. Acylchlorides, nomenclature, synthesis and their reactivity

 

13. Anhydrides and esters, nomenclature, synthesis and their reactivity

 

14.Amides and nitriles, nomenclature, synthesis and their reactivity

 

15. Reactivity of benzenediazonium salts, azo-coupling reactions of diazonium salts with activated aromatic compounds

 

16. Reactivity of a,b-unsaturated carbonyl compounds

 

17. Oxidations

 

18. Reductions

 

19. Molecular rearrangements

 

20. Addition polymers

 

21. Condensation polymers

 

22. Organometallic compounds - preparation, reactivity

 

23. Amines, nomenclature, synthesis, reactivity

 

24. Sulphur containing compounds

 

25. Heterocyclic amines

 

26. b-Dicarbonyl compounds and their reactivity (The Claisen condensation, Malonic ester synthesis, Knoevenagel condensation, Michael addition, Mannich reaction)

 

27. Phenols - synthesis, reactivity

 

28.Amino acids, nomenclature, preparation, reactivity

 

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Czech

Podmínkou pro získání zápočtu je 100% účast na seminární výuce a zisk nejméně 60 % bodů z testů psaných v průběhu semestru nebo ze zápočtového testu. Zkouška má písemnou a ústní část. Splnění písemné části (60% bodů) předchází ústní část zkoušky. Jedna otázka je vzorec léčiva, jeho název, fyzikální vlatnosti a reaktivita a jedna otázka ze systému. 

Otázky ke zkoušce:

 

1.    Alkany, cykloalkany, názvosloví, příprava a reaktivita

 

2.     Alkeny, názvosloví, příprava (Zaitsevovo pravidlo), reaktivita (Markovnikovovo pravidlo)

 

3.    Dieny, polyeny, Diels-Alderovy reakce, alkyny, názvosloví, příprava a reaktivita

 

4.    Benzen, aromaticita, elektrofilní aromatická substituce, vliv substituentů na aromatickou substituci

 

5.    Nukleofilní aromatická substituce.

 

6.    Alkylhalogenidy, názvosloví, příprava a reaktivita (substituce, eliminace, porovnání s arylhalogenidy)

 

7.    Alkoholy, ethery, názvosloví, příprava a reaktivita

 

8.    Aldehydy, ketony, názvosloví, příprava a reaktivita

 

9.     Reakce aldehydů a ketonů s N-basemi, O-basemi a S-basemi, Haloformová reakce, oxidace a redukce karbonylových sloučenin

 

10. Reaktivita karbonylových sloučenin s C-H kyselinami, Aldolové a zkřížené Aldolové reakce

 

11. Kyseliny, názvosloví, příprava a reaktivita

 

12. Acylchloridy, názvosloví, příprava a reaktivita

 

13. Anhydridy a estery, názvosloví, příprava a reaktivita

 

14. Amidy a nitrily, názvosloví, příprava a reaktivita

 

15. Příprava a reaktivita diazoniových solí, azo-sloučeniny

 

16. Reaktivita a,b-nenasycených karbonylových sloučenin

 

17. Oxidace organických sloučenin

 

18. Redukce

 

19. Molekulární přesmyky

 

20. Adiční polymery

 

21. Kondenzační polymery

 

22. Organokovové sloučeniny, názvosloví, příprava a reaktivita

 

23. Aminy, názvosloví, příprava a reaktivita

 

24. Sloučeniny obsahující síru, názvosloví, příprava a reaktivita

 

25. Heterocyklické sloučeniny

 

26. b-Dikarbonylové sloučeniny a jejich reaktivita (Claisenova kondensace, Malonesterová syntéza, Knoevenagelova kondenzace, Michaelova adice, Mannichova reakce)

 

27. Fenoly, názvosloví, příprava a reaktivita

 

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Literature

English

Obligatory:

• Solomons, T. W. Graham Fryhle, Craig B.. Organic chemistry. Hoboken: John Wiley, 2007, 1191 s. ISBN 0-471-68496-1.
• Wade, L. G.. Organic chemistry. Englewood Cliffs: Prentice Hall Int., 1987, 1233 s. ISBN 0-13-642588-7.
• McMurry, Susan McMurry, John. Study guide & student solutions manual for John McMurry's Organic chemistry. Belmont: Thomson-Brooks/Cole, 2008, 900 s. ISBN 978-0-495-11268-6.

Last update: prepocet_literatura.php (19.09.2024)

Czech

Povinná:

• McMurry, John. Organic chemistry. Pacific Grove: Brooks/Cole, 1996, 1243 s. ISBN 0-534-23832-7.
• Wade, L. G.. Organic chemistry. Englewood Cliffs: Prentice Hall Int., 1987, 1233 s. ISBN 0-13-642588-7.
• Solomons, T. W. Graham Fryhle, Craig B.. Organic chemistry. Hoboken: John Wiley, 2007, 1191 s. ISBN 0-471-68496-1.

Last update: prepocet_literatura.php (19.09.2024)

Syllabus

English

System of organic compounds

Alkanes, cycloalkanes, alkenes, polyenes, alkynes, aromates, halogen derivatives, alcohols, phenols, ethers, amines, organic compounds of sulphur and silicon, carbonyl compounds and their reactivity, carboxylic acids and their derivatives, acylchlorides, anhydrides, esters, amides, nitriles, amino acids, organometallic compounds, heterocyclic compounds.

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Czech

Systém organických sloučenin

Alkany, cykloalkany, alkeny, polyeny, alkyny, halogenderiváty, alkoholy, fenoly, ethery, aminy, sloučeniny síry a křemíku, karbonylové sloučeniny a jejich reaktivita, karboxylové kyseliny a jejich deriváty, acyl chloridy, anhydridy, estery, amidy, nitrily, aminokyseliny, organokovové sloučeniny, heterocykly

Last update: Vinšová Jarmila, prof. RNDr., CSc. (20.02.2024)

Learning outcomes

  

Workplace: Department of Organic and Bioorganic Chemistry, Charles University, Faculty of Pharmacy in Hradec Králové

 

Course title: GAF299 Organic Chemistry II

 

General learning Outcomes

 

A.  Prerequisite: Skills required from Organic Chemistry I:

·         Find and name all functional groups in the drug formula or find the specified functional group in the drug formula

·         Find and name all heterocycles in the drug formula and determine which heteroatom is present in the ring

·         Find the stereocentres in the given structure and discuss the maximum number of stereoisomers

·         Identify the aromatic rings in the given molecule and explain

·         Discuss the spatial arrangement of rings in a given molecule

·         Predict the acid-base properties of a given compound; comment on the acidity or basicity of specific functional groups (e.g., discuss the basicity of various nitrogen functional groups)

·         Predict the approximate aqueous solubility of a given compound; discuss the contributions of individual functional groups or structural fragments to aqueous solubility

·         Discuss ways to increase the solubility of a given substance in water (using acid-base reactions)

 

B.  By the end of the module, students should be able to…..

·         Write reaction schemes for the preparation of a given product from a given reactant(s) (the synthesis may have more than one step).

·         Write a detailed mechanism for the reaction of a given reactant(s) with a given reagent (under given conditions).

·         Explain the course of a given reaction using resonance structures.

·         Explain the influence of inductive or mesomeric effects on the course of a given reaction or the reactivity of a given functional group.

·         Decide whether a given compound will react with a given reagent and what, if anything, will be produced.

·         Sugest an appropriate reagent to achieve a specified reaction.

·         Select an appropriate reactant that can be used for a specified reaction.

·         Describe and explain the similarities and differences between the preparations of two given compounds.

·         Complete the formulae of unknown substances A, B, C in a given reaction scheme.

·         Decide whether a given reaction will take place.

·         Classify a given reaction as an addition, elimination, substitution or rearrangement.

·         Identify the electrophile/nucleophile in a given reaction.

 

 

For details of the module syllabus, see the corresponding content document.

Last update: Kitson Russell Richard Anthony, doc. Dr. (14.03.2025)