Organic Chemistry

Data

Official data in SubjectManager for the following academic year: 2023-2024

Topic

Starting from saturated, unsaturated, aromatic hydrocarbons, students acquire knowledge of the most important physical and chemical properties of halogen, oxygen, nitrogen and sulfur (organogenic elements) containing compounds, basic relationships, synthetic methods and the biological significance of each group of compounds. A suitable molecular basis is provided to study the basic relationships between chemical structure and biological action.
During the laboratory practice an introduction to organic laboratory equipment and techniques will be provided and some selected characteristic reactions of different functional groups will be investigated.

Lectures

• 1. Introduction to the elements of organic chemistry (functional groups, acids and bases in organic chemistry, structure and bonding, organic reactions, basics of nomenclature); - Dr. Bognár Balázs
• 2. Introduction to the elements of organic chemistry (functional groups, acids and bases in organic chemistry, structure and bonding, organic reactions, basics of nomenclature); - Dr. Bognár Balázs
• 3. Hydrocarbons I (alkanes, alkenes, alkynes); - Dr. Bognár Balázs
• 4. Hydrocarbons I (alkanes, alkenes, alkynes); - Dr. Bognár Balázs
• 5. Hydrocarbons II (aromatic compounds, biologically active polyenes – carotenoids, steroids); - Dr. Bognár Balázs
• 6. Hydrocarbons II (aromatic compounds, biologically active polyenes – carotenoids, steroids); - Dr. Bognár Balázs
• 7. Stereochemistry: isomerism, conformation, configuration, chirality; - Dr. Bognár Balázs
• 8. Stereochemistry: isomerism, conformation, configuration, chirality; - Dr. Bognár Balázs
• 9. Alkyl halides (physical and chemical properties, nucleophilic substitution, their role in industry and environment); - Dr. Bognár Balázs
• 10. Alkyl halides (physical and chemical properties, nucleophilic substitution, their role in industry and environment); - Dr. Bognár Balázs
• 11. Alcohols, phenols, ethers (structure, reactions, biological importance); - Dr. Bognár Balázs
• 12. Alcohols, phenols, ethers (structure, reactions, biological importance); - Dr. Bognár Balázs
• 13. Nitrogen containing compounds (amines - structure, physical, chemical properties, biologically active amines, alkaloids); - Dr. Bognár Balázs
• 14. Nitrogen containing compounds (amines - structure, physical, chemical properties, biologically active amines, alkaloids); - Dr. Bognár Balázs
• 15. Sulfur containing compounds: thiols and sulfides (physical, chemical properties, importance in biological processes); - Dr. Bognár Balázs
• 16. Sulfur containing compounds: thiols and sulfides (physical, chemical properties, importance in biological processes); - Dr. Bognár Balázs
• 17. Aldehydes and ketones (structure, physical, chemical properties, reactions, important representatives); - Dr. Bognár Balázs
• 18. Aldehydes and ketones (structure, physical, chemical properties, reactions, important representatives); - Dr. Bognár Balázs
• 19. Mono-, di- and polysaccharides: structure and biological importance; - Dr. Bognár Balázs
• 20. Mono-, di- and polysaccharides: structure and biological importance; - Dr. Bognár Balázs
• 21. Carboxylic acids and their derivatives (structure, physical, chemical properties, alpha-position substituted derivatives, di- and polycarboxylic acids, representatives); - Dr. Bognár Balázs
• 22. Carboxylic acids and their derivatives (structure, physical, chemical properties, alpha-position substituted derivatives, di- and polycarboxylic acids, representatives); - Dr. Bognár Balázs
• 23. Amino acids and proteins; - Dr. Bognár Balázs
• 24. Amino acids and proteins; - Dr. Bognár Balázs
• 25. Heterocycles (5- and 6-membered heteroaromatic compounds, structure, biologically important representatives, chemical mode of action of coenzymes); Vitamins; Nucleotides, nucleosides, nucleic acids; - Dr. Bognár Balázs
• 26. Heterocycles (5- and 6-membered heteroaromatic compounds, structure, biologically important representatives, chemical mode of action of coenzymes); Vitamins; Nucleotides, nucleosides, nucleic acids; - Dr. Bognár Balázs
• 27. Summary - Dr. Bognár Balázs
• 28. Summary - Dr. Bognár Balázs

Practices

• 1. Introduction: general safety rules in organic laboratory, reduction of risks; selected characteristic reactions of alkanes, alkenes, alkynes. Introduction to organic laboratory equipment and techniques I.: synthesis of acetanilide (heating, cooling, stirring, filtration, determination of melting point);
• 2. Introduction: general safety rules in organic laboratory, reduction of risks; selected characteristic reactions of alkanes, alkenes, alkynes. Introduction to organic laboratory equipment and techniques I.: synthesis of acetanilide (heating, cooling, stirring, filtration, determination of melting point);
• 3. Introduction: general safety rules in organic laboratory, reduction of risks; selected characteristic reactions of alkanes, alkenes, alkynes. Introduction to organic laboratory equipment and techniques I.: synthesis of acetanilide (heating, cooling, stirring, filtration, determination of melting point);
• 4. Introduction to organic laboratory equipment and techniques II.: preparation of tert-butyl-chloride (extraction, distillation, drying, determination of boiling point), selected characteristic reactions of aromatic hydrocarbons, alkyl and aryl halides, alcohols, phenols and ethers.
• 5. Introduction to organic laboratory equipment and techniques II.: preparation of tert-butyl-chloride (extraction, distillation, drying, determination of boiling point), selected characteristic reactions of aromatic hydrocarbons, alkyl and aryl halides, alcohols, phenols and ethers.
• 6. Introduction to organic laboratory equipment and techniques II.: preparation of tert-butyl-chloride (extraction, distillation, drying, determination of boiling point), selected characteristic reactions of aromatic hydrocarbons, alkyl and aryl halides, alcohols, phenols and ethers.
• 7. Selected characteristic reactions of amines, aldehydes, ketones and carbohydrates. Isolation of caffeine; thin layer chromatography;
• 8. Selected characteristic reactions of amines, aldehydes, ketones and carbohydrates. Isolation of caffeine; thin layer chromatography;
• 9. Selected characteristic reactions of amines, aldehydes, ketones and carbohydrates. Isolation of caffeine; thin layer chromatography;
• 10. Selected characteristic reactions of carboxylic acids and carboxylic acid derivatives, some heterocycles, amino acids and peptides.
• 11. Selected characteristic reactions of carboxylic acids and carboxylic acid derivatives, some heterocycles, amino acids and peptides.
• 12. Selected characteristic reactions of carboxylic acids and carboxylic acid derivatives, some heterocycles, amino acids and peptides.
• 13. Written test
• 14. Summary, evaluation.

Seminars

• 1. Recognizing functional groups, predicting hybridization and geometry, predicting the direction of acid-base reactions;
• 2. Reactivity alkanes, alkenes, alkynes, stability of radicals and carbocations;
• 3. Determining aromaticity, reactivity of aromatic compounds, directing rules in practice;
• 4. Stereochemistry: recognizing enantiomers, diastereomers, meso isomers, assigning configuration to chiral centers, representing 3D structures on paper (Fischer projection);
• 5. Nucleophilic substitution reactions with oxygen, nitrogen, sulphur and carbon centered nucleophiles;
• 6. Elimination reactions;
• 7. Basicity and nucleophilicity of amines;
• 8. Nucleophilic addition reactions on carbonyl compounds;
• 9. Drawing the structure of monosaccharides (chiral centers, Haworth projection);
• 10. Oxidation reactions of mono- and disaccharides (reducing and nonreducing sugars);
• 11. Interconversion of carboxylic acid derivatives;
• 12. pI of amino acids, some reactions;
• 13. Comparing aromatic heterocycles with benzene;
• 14. Summary of organic reactions: recognizing structure (functional groups) and reactivity relationship;

Reading material

Obligatory literature

John McMurry, Fundamentals of Organic Chemistry, International edition, 7th ed., 2011, 2007 Brooks/Cole Cengage Learning, Belmont, ISBN-13: 978-1-4390-4973-0; ISBN-10: 1-4390-4973-4
A. Winter: Organic Chemistry 1 for Dummies, 2nd ed., 2016, Wiley, ISBN: 1119293375

Literature developed by the Department

The slides of the lectures will be uploaded to the neptun MeetStreet or Teams files.
The questions discussed in the seminar are also uploaded to Teams.

Notes

Tamás Kálai, Balázs Bognár, Organic Chemistry Laboratory Manual for English Speaking Students, Department of Organic and Medicinal Chemistry, University of Pécs, 2010

Recommended literature

Harold Hart, Organic Chemistry A Short Course, International student edition, 8th ed, 1991 Houghton Mifflin Company, Boston, ISBN: 0-395-62838-5
Dr. James W. Zubrick, Organic Chem Lab Survival Manual: A Student’s Guide to Technics, 11th ed, Wiley; ISBN-13: 978-1119608554, ISBN-10: 1119608554

Conditions for acceptance of the semester

Maximum of 25 % absence allowed

Mid-term exams

At the end of the practice a written test must be completed over 50%.
Students write short midterm tests from the questions discussed in the seminar on 3rd, 5th, 7th, 9th and 11th week and at least three of them must be completed better than 50 %. Two midterm test will be written from the subject of the lecture. Those who can complete all (practice, seminar, lecture) tests at least 80 % grade 5 will be proposed.

Making up for missed classes

Students should consult with the lecturer or with the teaching assistant.

Exam topics/questions

1. Aliphatic hydrocarbons: alkanes, alkenes, alkynes; biologically active polyenes – carotenoids, steroids;
2. Aromatic hydrocarbons;
3. Stereochemistry: isomerism, conformation, configuration, chirality;
4. Alkyl and aryl halides: physical and chemical properties, nucleophilic substitution, their role in industry and environment;
5. Alcohols, phenols, ethers: structure, reactions, biological importance;
6. Nitrogen containing compounds: amines - structure, physical, chemical properties, biologically active amines, alkaloids;
7. Sulfur containing compounds: thiols and sulfides (physical, chemical properties, importance in biological processes);
8. Aldehydes and ketones: structure, physical, chemical properties, reactions, important representatives;
9. Mono-, di- and polysaccharides: structure and biological importance;
10. Carboxylic acids and their derivatives: structure, physical, chemical properties, alpha-position substituted derivatives, di- and polycarboxylic acids, representatives;
11. Amino acids and proteins;
12. Heterocycles: 5- and 6-membered heteroaromatic compounds; Nucleotides, nucleosides, nucleic acids; Biologically important representatives;

Examiners

• Dr. Bognár Balázs
• Dr. Kálai Tamás
• Pápayné Dr. Sár Cecilia

Instructor / tutor of practices and seminars

• Dr. Bognár Balázs
• Dr. Kálai Tamás
• Pápayné Dr. Sár Cecilia