Organic Chemistry 2 - Theory

Data

Official data in SubjectManager for the following academic year: 2024-2025

Topic

This subject is a part of chemistry basics. Its aim is to present the nomenclature, structure, physical and chemical properties, synthesis, reaction mechanisms and application of organic compounds.

Lectures

• 1.

  Nitro compounds: electronic structure, physical, chemical properties, synthesis, reduction of nitro compounds, aromatic nucleophilic substitution, nitro-aldol reaction, biologically important nitro compounds.

  - Pápayné Sár Cecilia
• 2.

  Nitro compounds: electronic structure, physical, chemical properties, synthesis, reduction of nitro compounds, aromatic nucleophilic substitution, nitro-aldol reaction, biologically important nitro compounds.

  - Pápayné Sár Cecilia
• 3.

  Application of nitro compounds in organic syntheses.

  - Pápayné Sár Cecilia
• 4.

  Amino compounds: Physical, chemical properties, basicity of amines.

  - Pápayné Sár Cecilia
• 5.

  Synthesis of amines: nucleophilic substitution, Gabriel synthesis, Hoffmann degradation, Curtius rearrangement, reduction of amides and nitriles.

  - Pápayné Sár Cecilia
• 6.

  Reactions of amines: alkylation, acylation, Hinsberg's probe, oxydation, diazonium salts.

  - Pápayné Sár Cecilia
• 7.

  Biologically important amines derived from amino acid decarboxylation.

  - Pápayné Sár Cecilia
• 8.

  Alkaloids: definition and some representatives.

  - Pápayné Sár Cecilia
• 9.

  Aldehydes and ketones: electronic structure of carbonyl group, enol-oxo tautomerism, physical, chemical properties, synthesis of aldehydes and ketones, nucleophilic addition.

  - Pápayné Sár Cecilia
• 10.

  Aldehydes and ketones: electronic structure of carbonyl group, enol-oxo tautomerism, physical, chemical properties, synthesis of aldehydes and ketones, nucleophilic addition.

  - Pápayné Sár Cecilia
• 11.

  Aldehydes and ketones: substitution on alpha carbon; Some representative oxo compounds; Quinones, vitamin K.

  - Pápayné Sár Cecilia
• 12.

  Carbohydrates: classification of carbohydrates, hemiacetal formation, mutarotation, D- and L-sugars; alpha- and beta-anomers.

  - Pápayné Sár Cecilia
• 13.

  Carbohydrates: classification of carbohydrates, hemiacetal formation, mutarotation, D- and L-sugars; alpha- and beta-anomers.

  - Pápayné Sár Cecilia
• 14.

  Chemical-physical properties of carbohydrates: oxidation, acetylation, bromination, formation of O- and N-glycosides. Epimerization. Formation of fructose 1,6-diphosphate in aldol reaction.

  - Pápayné Sár Cecilia
• 15.

  Chemical-physical properties of carbohydrates: oxidation, acetylation, bromination, formation of O- and N-glycosides. Epimerization. Formation of fructose 1,6-diphosphate in aldol reaction.

  - Pápayné Sár Cecilia
• 16.

  Function and structure of oligosaccharides and polysaccharides; Reducing and non-reducing sugars, the invert sugar.

  - Pápayné Sár Cecilia
• 17.

  Chemical reactions of oligosaccharides.

  - Pápayné Sár Cecilia
• 18.

  Carboxylic acids and their derivatives: Electronic structure of carboxylic acids and their derivatives. Formation and reactivity of carboxylic acid derivatives, acidity of carboxylic acids. Physical and chemical properties of carboxylic acids.

  - Pápayné Sár Cecilia
• 19.

  Carboxylic acids and their derivatives: Electronic structure of carboxylic acids and their derivatives. Formation and reactivity of carboxylic acid derivatives, acidity of carboxylic acids. Physical and chemical properties of carboxylic acids.

  - Pápayné Sár Cecilia
• 20.

  Some biologically important carboxylic acids; Structure of lipids and phospholipids

  - Pápayné Sár Cecilia
• 21. Alpha-substituted carboxylic acids: their structure, acidity, biological importance. - Pápayné Sár Cecilia
• 22.

  Alpha-substituted carboxylic acids: their structure, acidity, biological importance.

  - Kálai Tamás
• 23.

  Carbonic acid derivatives: syntesis, their utilization in amino acid synthesis and in drug industry.

  - Kálai Tamás
• 24.

  Carbonic acid derivatives: syntesis, their utilization in amino acid synthesis and in drug industry.

  - Kálai Tamás
• 25.

  Amino acids, peptides: physical and chemical properties of amino acids (zwitterion formation, chirality) peptide link formation, amino acid synthesis.

  - Kálai Tamás
• 26.

  Amino acids, peptides: physical and chemical properties of amino acids (zwitterion formation, chirality) peptide link formation, amino acid synthesis.

  - Kálai Tamás
• 27.

  Peptide synthesis, structure of proteins, general features of proteins and their classification.

  - Kálai Tamás
• 28.

  5-Membered heterocycles with one or two heteroatoms: classification of heterocycles, their nomenclature, electronic structure, aromaticity, aromatic electrophilic substitution, basicity, virtual tautomerism.

  - Kálai Tamás
• 29.

  5-Membered heterocycles with one or two heteroatoms: classification of heterocycles, their nomenclature, electronic structure, aromaticity, aromatic electrophilic substitution, basicity, virtual tautomerism.

  - Kálai Tamás
• 30.

  Most important and biologically important representatives of 5-membered heterocycles

  - Kálai Tamás
• 31.

  6-Membered heterocycles with one or two heteroatoms: their nomenclature, basicity, electronic structure, enol-oxo, amino-imino tautomerism, aromatic electrophilic substitution, nucleophilic substitution.

  - Kálai Tamás
• 32.

  6-Membered heterocycles with one or two heteroatoms: their nomenclature, basicity, electronic structure, enol-oxo, amino-imino tautomerism, aromatic electrophilic substitution, nucleophilic substitution.

  - Kálai Tamás
• 33.

  Most important and biologically active representatives of 6-membered heterocyles.

  - Kálai Tamás
• 34.

  Bases of nucleic acids. Structure of nucleic acids, chemical background to mutations.

  - Kálai Tamás
• 35.

  Bases of nucleic acids. Structure of nucleic acids, chemical background to mutations.

  - Kálai Tamás
• 36.

  Nucleic acid derivatives in drug synthesis.

  - Kálai Tamás
• 37.

  Vitamins: classification of vitamins and their biological role. Fat soluble vitamins.

  - Kálai Tamás
• 38.

  Vitamins: classification of vitamins and their biological role. Water soluble vitamins.

  - Kálai Tamás
• 39.

  Vitamins: classification of vitamins and their biological role. Water soluble vitamins.

  - Kálai Tamás
• 40.

  Examples for solving exam questions.

  - Kálai Tamás
• 41.

  Examples for solving exam questions.

  - Kálai Tamás
• 42.

  Summary

  - Kálai Tamás

Practices

Seminars

Reading material

Obligatory literature

John McMurry, Eric Simanek: Fundamentals of Organic Chemistry, 6th ed., Thomson Brooks, Belmont, 2007.

Literature developed by the Department

The slides of the lectures are available on neptun Meet Street.

Notes

Recommended literature

T. W. Graham Solomons: Organic Chemistry, 7th edition, Wiley and Sons, New York, 2000.

William H. Brown: Organic Chemistry, Saunders College Publishing, Fort Worth, 1995.

Conditions for acceptance of the semester

Further criterion of admission to the exam is the successful completion of the practice carried out in paralell (midsemester grade with the result different from failed).

Mid-term exams

Students write tests from the subject of the lecture on 3rd, 5th, 7th, 9th and 11th week and at least three of them must be completed better than 50 %. Those who can not complete these tests can not admit to the exam.

Making up for missed classes

Students have to contact the lecturer of the subject.

Exam topics/questions

1. Alkanes: Orbital hybridization and the structure of alkanes; Nomenclature, physical and chemical properties, combustion, free radical chlorination, conformation, cycloalkanes, type of ring strains, demonstrate with examples.

2. Unsaturated hydrocarbons: sp2 and sp hybridization, nomenclature, physical properties, reactions and synthesis of alkenes and alkynes. Electrophilic addition, Markovnikov's rule, 1,2- and 1,4-addition, conjugated and cumulated dienes.

3. Importance of unsaturated hydrocarbons in industry and biology: polymerization, isoprene, terpenes, steroids, carotenoids, polymers, rubber

4. Aromatic compounds: the structure of benzene, Hückel's rule. Electrophilic aromatic substitution reactions. (Nitation, sulfonation, bromination, Friedel-Crafts reactions), direction rules, classification of substituents, polyaromatics: examples, their chemical reactions aromatic electophilic substitution, oxidation.

5. Alkyl halides: the character of C-X bonds, physical properties, reactivity of alkyl halides, synthesis of alkyl and aromatic halides, and reactions of alkyl halides (substitution, elimination); Organic halides in the environment.

6. Organometallic compounds: their structure, their importance in organic syntheses (Mg, Na, Li, Si, Cu, Cd compounds).

7. Alcohols, phenols, ethers: Structure, physical and chemical properties, reactions; Their biological importance.

8. Stereochemistry: isomerism, absolute and relative configuration, chirality, racemates, diastereomers, polarimetry, resolution.

9. Sulfur containing compounds: Physical, chemical properties, importance in biological processes (in amino acids, peptides, methylation in biology, AcCo-A, drugs, sulfonamides, penicillin, cefalosporin).

10. Nitro compounds: electronic structure, physical, chemical properties, synthesis (including aromatic electrophilic nitration), reduction of nitro compounds, their nitro-aldol reaction, biologically important nitro compounds (glycerine trinitrate, chloroamphenicol).

11. Amino compounds - Physical, chemical properties, basicity of amines (compare aniline, ammonia, methylamine, dimethylamine etc.) their possible synthesis (alkylation of ammonia, Gabriel synthesis, reductive amination, Hofmann rearrangement), reactions: Hinsberg reaction, oxidation of amines, reaction with HNO2.

12. Biologically important amines: structure and properties of histamine, tryptamine, choline, acetylcholine, taurine, putrescine, adrenaline; Alkaloids: definition (structure of mescaline, nicotine, coniine, quinine, papaverine, morphine)

13. Aldehydes and ketones: electronic structure of carbonyl group, enol-oxo tautomerism, physical, chemical properties, synthesis of aldehydes and ketones, their reaction: aldol condensation, Canizzaro-reaction, Silver mirror/Fehling test, oxidation, reaction with amines, hydrazines, Grignard-reagent, oximes, Beckmann-rearrangement, ketenes, quinones, vitamin K.

14. Carbohydrates: classification of carbohydrates (ketose, aldose, pyranose, furanose, pentose, hexose), hemiacetal formation, mutarotation, D- and L-sugars; alpha- and beta-anomers. Chemical-physical properties of carbohydrates. The following covalent structures are required: glucose, fructose, mannose, galactose, ribose, 2-deoxy-ribose, glyceraldehyde, ascorbic acid. Oxidation of carbohydrates, acetylation, bromination, formation of O- and N-glycosides. Epimerization (glucose, mannose, fructose). Formation of fructose 1,6-diphosphate in aldol reaction.

15. Function and structure of oligosaccharides and polysaccharides: sucrose, maltose, cellobiose, lactose, kitine, pectine, cellulose, starch. Reducing sugars and non-reducing sugars, the invert sugar. Chemical reactions of oligosaccharides.

16. Carboxylic acids and their derivatives (acyl chlorides, anhydrides, esters, amides): Electronic structure of carboxylic acids and their derivatives. Formation of carboxylic acids and their derivatives. Reactivity of carboxylic acid derivatives, acidity of carboxylic acids. Physical and chemical properties of carboxylic acids. Ester synthesis, Claisen-condensation. Most important carboxylic acids: formic acid, acetic acid, benzoic acid, oleic acid, linolic and linoleic acid, palmitic and stearic acids, structure of lipids and phospholipids.

17. Alpha-substituted carboxylic acids and carbonic acid: halogenation, lactic acid, pyruvic acid, malonic acid, malonic acid synthesis, oxalic acid, malic acid, maleic acid, fumaric acid, citric acid. Their structure, acidity, biological importance. Carbonic acid derivatives: carbonic acid and its esters, phosgene, chloroformic acid esters and their utilization in amino acid synthesis, urea, thiourea, diureides, barbituric acid and its derivatives, guanidine, creatine.

18. Amino acids, peptides: the exact covalent structure of 20 amino acids, physical and chemical properties (zwitterion formation, chirality) peptide link formation, amino acid synthesis, glutathione, peptide synthesis, structure of proteins (primary, secondary, tertiary, quaternary), general features of proteins, their classification with examples, denaturation and colour-reactions of proteins (Xantoprotein-test, Millon-test etc.)

19. 5-Membered heterocycles: classification of heterocycles, their nomenclature, most important representatives: furane, thiophene, pyrrole. Heterocycles with two heteroatoms: oxazole, thiazole, imidazole, their electronic structure, aromaticity, aromatic electrophilic substitution, basicity, virtual tautomerism. Biologically important representatives: biotin, ultraseptil, histamine, penicillins, aminophenazone, furfural; Indole and its derivatives: serotonine, auxins, indigo.

20. 6-Membered heterocycles: their nomenclature, most important representatives: pyridine, quinoline, isoquinoline, pyrilium, benzpyrilium cation, their basicity, electronic structure, eno-oxo amino-imino tautomerism, aromatic electrophilic substitution, nucleophilic substitution, biologically important derivatives: rutin, vitamin E, cyanidium chloride, tetrahydrocannabinol, nicotinamide, quinine, papaverine, vitamin B6, isoniazide, nifedipine, barbituric acid: veronal, sevenal bases of nucleic acids, base pairs cytosine, guanine, adenine, timine, uracil, their exact covalent structure, structure of DNA, RNA, vitamin B1, purine: caffeine, theophylline, theobromine, xanthine, pteridine, structure and function of folic acid.

21. Vitamins: classification of vitamins, their exact covalent structure, their biological role. Vitamin A, vitamin D, Vitamin E, vitamin K, Vitamin B1, Vitamin B3, Vitamin B5, the role and function of the NAD, Vitamin B6, Vitamin B7, inosite, p-aminobenzoic acid, folic acid, Vitamin B12, Vitamin C, Vitamin P and flavonoids, Vitamin U.

Examiners

• Bognár Balázs
• Kálai Tamás
• Pápayné Sár Cecilia

Instructor / tutor of practices and seminars

• Bognár Balázs
• Kálai Tamás